Handbook of and Related

Naoyuki Taniguchi • Koichi Honke Minoru Fukuda • Hisashi Narimatsu Yoshiki Yamaguchi • Takashi Angata Editors

Handbook of Glycosyltransferases and Related Genes

Second Edition Editors Naoyuki Taniguchi Yoshiki Yamaguchi RIKEN-Max-Planck Joint Research Center RIKEN-Max-Planck Joint Research Center for Systems Chemical Biology, RIKEN for Systems Chemical Biology, RIKEN Wako, Saitama, Japan Wako, Saitama, Japan

Koichi Honke Takashi Angata Department of Biochemistry Institute of Biological Chemistry Kochi University Medical School Academia Sinica Nankoku, Kochi, Japan Taipei, Taiwan

Minoru Fukuda Sanford Burnham Medical Research Institute La Jolla, CA, USA

Hisashi Narimatsu Research Center for Medical Glycoscience (RCMG) National Institute of Advanced Industrial Science and Technology (AIST) Tsukuba, Ibaraki, Japan

ISBN 978-4-431-54239-1 ISBN 978-4-431-54240-7 (eBook) ISBN 978-4-431-54241-4 (print and electronic bundle) DOI 10.1007/978-4-431-54240-7 Springer Tokyo Heidelberg New York Dordrecht London

Library of Congress Control Number: 2014930991

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Springer is part of Springer Science+Business Media (www.springer.com) Preface

Almost ten years have passed since the publication of the first edition of this book in 2002, and it is timely to renew and publish a second edition, because a large number of glycosyltransferases has been characterized since then. In the second edition, Springer introduced an online system for receiving a submitted manuscript of each chapter, which helped us to handle more than one hundred manuscripts much easier, and before publishing the printed version of the book, online articles are now being made available. It is no doubt that glycoscience has been, and will be in the future, playing a pivotal role in various fields of research in the life sciences. Last year, the US National Academy of Sciences published a report entitled “Transforming Glycoscience, A Roadmap for the Future.” This report emphasizes the role of glycans in health, energy and material science. However, many issues related to the structure and function of glycans remain to be clarified, and characterizing the structure and function of glycosyltransferases is essential for our understanding of glycans in health and disease. Moreover, technology is now a very common technique and many KO or transgenic mice have been developed which has permitted possible implication of various diseases such as autoimmune disease, diabetes, chronic obstructive pulmonary disease, and cancer metastasis, and auto- immune diseases to be clarified. In addition, the cause of some of the CGD (congenital disorders of glycosylation) including muscle dystrophy was found to be due to the lack of, or a mutation in, a certain gene. At present, almost 200 glycosyltransferase genes have been identified and encompass approximately 1 % of the whole . There are still many with unknown functions which belong to the glycosyltransferase family or its related genes. In this edition, 160 glycosyltransferases are listed and additional information such as X-ray crystallographic data and UniProt number have been also included. It is also known that the expression levels of glycosyltransferases are regulated by various factors such as nucleotide sugar levels, nucleotide transporter levels, chaperons, acceptor substrate levels, genetic or epigenetic regulation via transcrip- tion factors etc., and also their availability in the Golgi or ER etc. However, those underlying mechanisms of glycosyltransferase regulation are largely unknown. It is also not clear at present how glycosyltransferases act on specific glycoprotein(s) as acceptor substrates and how monosaccharide(s) are added at a specific site of the

v vi Preface proteins and expressed in a tissue/cell/organ specific manner. These issues should be cleared in the next decade and will open a new field of glycobiology. Regarding industrial or pharmaceutical applications of glycosyltransferases, such as the synthesis of glycans using glycosyltransferases, it is still difficult for us to use a sole glycosyltransferase to synthesize glycans and/or glycoproteins, glycolipids and . Therefore a combination of glycosyltransferase and chemistry, namely, chemo-enzymatic techniques were being used. The biological significance of glycosyltransferases in terms of the growth and development, immune-system neuroscience, stem cell research, cancer biomarker discovery and antibody therapy etc. are still important areas of research which will likely develop in the future. This book is dedicated to the late Professor Robert Hill who was a genuine pioneer in the field of glycosyltransferase enzymology and the purification of glycosyltransferases which opened a new field of research for glycosyltransferase genes and their functions. Finally we wish to express our sincere thanks to all authors who took the time to contribute to this monograph. We particularly thank Ms. Fumi Ota at RIKEN Systems Glycobiology Research Group, who helped us in publishing this book. Finally we are very grateful to all staff members of the Springer Japan KK and Springer who generously edited the original draft of this book and the online version.

October 10, 2013 Naoyuki Taniguchi Koichi Honke Minoru Fukuda Hisashi Narimatsu Yoshiki Yamaguchi Takashi Angata Editors About the Editors

Naoyuki Taniguchi Group Director, RIKEN-Max-Planck Joint Research Center for Systems Chemical Biology, RIKEN, Wako, Saitama, Japan

Naoyuki Taniguchi graduated from the Faculty of Medicine, Hokkaido University, and obtained his M.D. in 1967 and then Ph.D. in 1972 from the same university. He became Assistant Professor of the Department of Preventive Medicine, Hokkaido University, and Visiting Associate Professor at the Connell University Medical School, New York, in 1976. In 1986, he became Professor and Chair of the Department of Biochemistry at the Osaka University Medical School. In 2006, after retirement from the medical school, he became endowed Chair Professor of Osaka University. Meanwhile, he formed the Systems Glycobiology Research Group at RIKEN in 2007 and has been the Group Director since. His focus is on the structure and function of glycans, especially the role of N-linked glycoproteins in relation to the mechanism of the disease biomarker discovery and therapeutics. He has received several distinguished awards, such as IGO (International Glycoconjugate Organization) Award in 2001, Medal with Purple Ribbon from the Emperor of Japan in 2005, HUPO (Human Proteome Organization) Distinguished Service Award in 2009, and Japan Academy Prize in 2011. Taniguchi currently

vii viii About the Editors serves as editor and editorial board member of many journals such as Journal of Biological Chemistry, Biochemical and Biophysical Research Communications, Proteomics, etc., and he himself has published more than 400 original papers and more than 50 reviews. He also served as President in the 75th Annual Meeting of the Japanese Biochemical Society and as Secretary General in the 20th IUBMB 11FAOBMB Congress. Recently, he has been elected as the President of the Society for Glycobiology for 2014. About the Editors ix

Koichi Honke Professor, Department of Biochemistry, Kochi University Medical School, Nankoku, Kochi, Japan

Koichi Honke is a Professor at Kochi University Medical School in Kochi, Japan. Honke graduated from Hokkaido University School of Medicine obtaining his M.D. in 1983. Since he started his research under the supervision of Prof. Akira Makita at Cancer Institute, Hokkaido University Medical School, in 1984, Honke has been studying the and function of glycolipids as well as glycoproteins. Honke worked at Osaka Medical Center for Maternal and Child Health as Chief Researcher from 1995 to 1999, with Dr. Yoshinao Wada, and in the Department of Biochemistry, Osaka University Medical School, as Associate Professor from 1999 to 2003, with Prof. Naoyuki Taniguchi. Honke was then promoted to Full Professor of the Kochi Medical School in 2003. Honke published over 110 original scientific papers, authored and edited many books, and served as Editor for Journal of Biochemistry. His major contribution has been purification, molecular cloning, and gene targeting of a glycan responsible for the biosynthesis of sulfatides and discovery of the ßGal 3-O-sulfotransferase gene family. Currently his research focus has shifted to the biogenesis of the membrane microdomains with establishment of a novel labeling method called EMARS for the identification of cell surface molecular clustering in living cells. x About the Editors

Minoru Fukuda Professor, Sanford Burnham Medical Research Institute, La Jolla, CA, USA

Minoru Fukuda is a Professor at Sanford-Burnham Medical Research Institute in La Jolla, California, and an Adjunct Professor in the Department of Pathology at the University of California, San Diego. Fukuda earned his Ph.D. in Biochemistry from the University of Tokyo, Japan, in 1973, and completed post doctoral research training at the Yale University School of Medicine. Fukuda was Assistant Professor at the University of Washington and Fred Hutchinson Cancer Research Center in Seattle, WA, working with Dr. Senichiro Hakomori, before he was recruited to the Burnham Institute as Director of the Glycobiology Program in 1984. In 1994–1995, Fukuda was also Biochemistry Chair of the Institute of Medical Science, University of Tokyo. Fukuda published over 280 original scientific papers, authored and edited many books, and served as Executive Editor and Associate Editor for BBA and Cancer Research, respectively. Fukuda received the Karl Meyer Award given by the Society for Glycobiology, The Mizutani Award, the MERIT Award, the Pro- gram Project Grant, and, recently, Alliance of Glycobiologists from the National Cancer Institute, NIH. His research focus is on structure, biosynthesis, and function of glycoproteins. He is particularly interested in tumor suppressor function of carbohydrates and for cellular signals in cell-cell interaction. About the Editors xi

Hisashi Narimatsu Director, Research Center for Medical Glycoscience (RCMG), National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan

Hisashi Narimatsu started his scientific carrier at the Keio University School of Medicine, where he earned his M.D. in 1974 and Ph.D. in 1979, then moved to the National Cancer Institute at the National Institutes of Health (NIH) in the USA as a postdoctoral fellow. He returned to Japan and became an Associate Professor at the Keio University School of Medicine and a Professor at the Institute of Life Science, Soka University, in 1991. In 2001, he joined the Institute of Molecular and Cell Biology of AIST, the former organization of RCMG, and has been the Director of RCMG since 2006. He served as the leader of several national projects including a series of the New Energy and Industrial Technology Development Organization (NEDO) Projects, and, currently, the Integrated Database Project funded by the Ministry of Education, Culture, Sports, Science and Technology. He also serves as a Professor of the Graduate School of Comprehensive Human Sciences, Tsukuba University, a Visiting Professor of the School of Medicine, Keio University, and an Advisory Professor for the Shanghai Jiao Tong University. He has received various awards including the Nikkei BP Technological Award (2007), Chemistry-Bio Tsukuba Award (2010), Tsukuba Award (2011), and JHUPO Award (2013). His specialties are glycobiology, biochemistry, , microbiology, and tumor biology, but the main theme of Narimatsu has been the clinical application of glycoscience. xii About the Editors

Yoshiki Yamaguchi Team Leader, RIKEN-Max-Planck Joint Research Center for Systems Chemical Biology, RIKEN, Wako, Saitama, Japan

Yoshiki Yamaguchi received his Ph.D. in 1998 at the Graduate School of Pharmaceutical Sciences, University of Tokyo (with Profs. Ichio Shimada and Yoji Arata), Japan. He continued his research as a Postdoctoral Research Fellow and then as a Research Associate in the same group. From 2001 to 2007, he was a Lecturer at Nagoya City University (with Prof. Koichi Kato) and then moved to his current position at RIKEN, Systems Glycobiology Research Group, as a Team Leader of the Structural Glycobiology Team. Yamaguchi has been holding posts concurrently in Nagoya City University (2007–) and in Tokyo Medical and Dental University (2008–) as a Visiting Professor and also in Fukushima Medical Univer- sity (2011–) as a contract lecturer. Yamaguchi received Young Scientist Awards from GlycoTOKYO in 2006 and from the Japanese Society of Carbohydrate Research in 2007. The Structural Glycobiology Team was formed with the aim of determining the 3D structure of such carbohydrate chains and lectins to gain knowledge of their function. In order to achieve this, his team is developing a multidisciplinary and comprehensive strategy based on a combination of nuclear magnetic resonance (NMR) spectroscopy, X-ray crystallography, synthetic chem- istry, and bioinformatics. His current study focuses on the development of NMR techniques for structural analyses of glycans, glycoproteins, and glycan-related proteins. About the Editors xiii

Takashi Angata Associate Research Fellow, Institute of Biological Chemistry, Academia Sinica, Taipei, Taiwan

Takashi Angata is an Associate Research Fellow at the Institute of Biological Chemistry, Academia Sinica, Taiwan. Angata received his Ph.D. degree in Bio- chemistry from the Graduate School of Science, University of Tokyo, Japan, in 1998. He completed his post doctoral training under Prof. Ajit Varki at the University of California, San Diego (1998–2003). After his return to Japan, he served as Research Scientist at the National Institute of Advanced Industrial Science and Technology (AIST; 2003–2009), Specially Appointed Associate Pro- fessor at Osaka University (2009–2011), and Team Leader at RIKEN Advanced Science Institute (2011–2013). He joined the Institute of Biological Chemistry, Academia Sinica, in 2013. Angata contributed to the expansion of the Siglec family of sialic acid recogni- tion proteins and made seminal discoveries in the field (such as concerted evolution of activating and inhibitory Siglecs as paired receptors), and published over 20 original research papers and reviews on the subject. His current research is focused on the role of activating Siglecs in innate immunity and chronic diseases.

Contents

Volume 1

Section I ...... 1

1 UDP-Glucose: Ceramide (UGCG) ...... 3 Yoshio Hirabayashi and Yohei Ishibashi

2 UDP-Glucose: Glycoprotein Glucosyltransferase 1,2 (UGGT1,2) ...... 15 Armando J. Parodi, Julio J. Caramelo, and Cecilia D’Alessio

3 Beta-1,3-Glucosyltransferase (B3GALTL) ...... 31 Takashi Sato and Hisashi Narimatsu

4 O-Glucosyltransferases Rumi (RUMI) ...... 39 Hideyuki Takeuchi and Robert S. Haltiwanger

Section II ...... 49

5 UDP-Gal: BetaGlcNAc Beta 1,4-, Polypeptide 1 (B4GALT1) ...... 51 Boopathy Ramakrishnan and Pradman K. Qasba

6 UDP-Gal: BetaGlcNAc Beta 1,4-Galactosyltransferase, Polypeptide 2-6; Xylosylprotein Beta 1,4-Galactosyltransferase, Polypeptide 7 (Galactosyltransferase I) (B4GALT2-7) ...... 63 Kiyoshi Furukawa, Henrik Clausen, and Takeshi Sato

7 UDP-Gal: BetaGlcNAc Beta 1,3-Galactosyltransferase, Polypeptide 1,2 (B3GALT1,2) ...... 73 Malene Bech Vester-Christensen, Lars Hansen, and Henrik Clausen

8 UDP-Gal: BetaGlcNAc Beta 1,3-Galactosyltransferase, Polypeptide 4 (B3GALT4) ...... 81 Koichi Furukawa, Yuhsuke Ohmi, and Keiko Furukawa

xv xvi Contents

9 UDP-Gal: BetaGlcNAc Beta 1,3-Galactosyltransferase, Polypeptide 5 (B3GALT5) ...... 89 Akira Togayachi and Hisashi Narimatsu 10 UDP-Gal: BetaGal Beta 1,3-Galactosyltransferase Polypeptide 6 (B3GALT6) ...... 101 Malene Bech Vester-Christensen, Lars Hansen, and Henrik Clausen

11 Glycoprotein Alpha 1,3-Galactosyltransferase 1, Pseudogene (GGTA1P) ...... 109 Shuji Miyagawa and Akira Maeda

12 Alpha 1,3-Galactosyltransferase 2, Pseudogene (A3GALT2P) . . 121 Dale Christiansen, Effie Mouhtouris, and Mauro S. Sandrin 13 UDP-Gal: Ceramide Galactosyltransferase (UGT8) ...... 131 Koichi Honke 14 UDP-Gal: Lactosylceramide Alpha 1,4-Galactosyltransferase (A4GALT) ...... 141 Koichi Furukawa, Yuji Kondo, and Keiko Furukawa 15 Core 1 b3Galactosyltransferase (C1GalT1, T-Synthase) and Its Specific Molecular Chaperone Cosmc (C1GalT1C1) ...... 149 Tongzhong Ju and Richard D. Cummings

Section III ...... 171

16 Protein O-Mannosyl- 1,2 (POMT1,2) ...... 173 Hiroshi Manya and Tamao Endo

Section IV N-Acetylglucosaminyltransferases ...... 181

17 Mannosyl (Alpha-1,3-)-Glycoprotein Beta-1,2-N- Acetylglucosaminyltransferase (MGAT1) ...... 183 Pamela Stanley 18 Mannosyl (Alpha-1,6-)-Glycoprotein Beta-1,2-N- Acetylglucosaminyltransferase (MGAT2) ...... 195 Brad Bendiak 19 Mannosyl (Beta-1,4-)-Glycoprotein Beta-1,4-N- Acetylglucosaminyltransferase (MGAT3); b1,4-N- Acetylglucosaminyltransferase III (GnT-III, GlcNAcT-III) .... 209 Yoshitaka Ikeda, Hideyuki Ihara, Hiroki Tsukamoto, Jianguo Gu, and Naoyuki Taniguchi 20 Mannosyl (Alpha-1,3-)-Glycoprotein Beta-1,4-N- Acetylglucosaminyltransferase, Isozyme A,B (MGAT4A,B) .... 223 Kazuaki Ohtsubo and Naoyuki Taniguchi Contents xvii

21 Mannosyl (Alpha-1,6-)-Glycoprotein Beta-1,6-N-Acetyl- Glucosaminyltransferase (MGAT5) ...... 233 James W. Dennis, Naoyuki Taniguchi, and Michael Pierce

22 Mannosyl (Alpha-1,6-)-Glycoprotein Beta-1,6-N-Acetyl- Glucosaminyltransferase, Isozyme B (MGAT5B) ...... 247 Kei-ichiro Inamori, Michael Pierce, and Naoyuki Taniguchi

23 Mannosyl (Alpha-1,3[6?]-)-Glycoprotein Beta-1,4-N- Acetylglucosaminyltransferase, Isozyme C (Putative) (MGAT4C) ...... 257 Tomohiko Taguchi

24 Fringe (UDP-GlcNAc: O-Fucosylpeptide ß1,3 N-Acetylglucosaminyltransferase) ...... 265 Robert S. Haltiwanger

25 UDP-GlcNAc: BetaGal Beta-1,3-N-Acetylglucosaminyltransferase 1 (B3GNT1), i- (iGnT) ...... 275 Minoru Fukuda

26 UDP-GlcNAc: BetaGal Beta-1,3-N-Acetylglucosaminyltransferase 2 (B3GNT2) ...... 283 Akira Togayachi and Hisashi Narimatsu

27 UDP-GlcNAc: BetaGal Beta-1,3-N-Acetylglucosaminyltransferase 3 (B3GNT3) ...... 295 Jiunn-Chern (Gene) Yeh and Minoru Fukuda

28 UDP-GlcNAc: BetaGal Beta-1,3-N-Acetylglucosaminyltransferase 4 (B3GNT4) ...... 303 Akira Togayachi and Hisashi Narimatsu

29 UDP-GlcNAc: BetaGal Beta-1,3-N-Acetylglucosaminyltransferase 5 (B3GNT5, Lc3Cer Synthase) ...... 311 Akira Togayachi and Hisashi Narimatsu

30 UDP-GlcNAc: Beta-Gal Beta1,3-N-Acetylglucosaminyltransferase 6 (B3GNT6) (Core 3 Synthase, C3GnT) ...... 321 Akira Togayachi and Hisashi Narimatsu

31 UDP-GlcNAc: BetaGal Beta-1,3-N-Acetylglucosaminyltransferase 7 (B3GNT7) ...... 331 Akira Seko

32 UDP-GlcNAc: BetaGal Beta-1,3-N-Acetylglucosaminyltransferase 8 (B3GNT8) ...... 337 Akira Togayachi and Hisashi Narimatsu xviii Contents

33 N-Acetyllactosaminide Beta-1,6-N-Acetylglucosaminyl-Transferase (GCNT2) (IGnT) ...... 347 Minoru Fukuda and Misa Suzuki-Anekoji 34 Beta-1,3-Galactosyl-O-Glycosyl-Glycoprotein Beta-1,6-N- Acetylglucosaminyltransferase 1 (GCNT1) (C2GnT-L) and Beta-1,3-Galactosyl-O-Glycosyl-Glycoprotein Beta-1,6-N- Acetylglucosaminyltransferase 3 (GCNT4) (C2GnT-T) ...... 355 Shigeru Tsuboi and Minoru Fukuda 35 Beta-1,3-Galactosyl-O-Glycosyl-Glycoprotein Beta-1,6-N- Acetylglucosaminyltransferase 3 (GCNT3) ...... 367 Jiunn-Chern (Gene) Yeh and Minoru Fukuda 36 Alpha-1,4-N-Acetylglucosaminyltransferase (A4GNT) ...... 379 Jun Nakayama 37 O-Linked N-Acetylglucosamine (GlcNAc) Transferase (UDP-N-Acetylglucosamine: Polypeptide-N- Acetylglucosaminyl Transferase) (OGT) ...... 393 Partha Banerjee and Gerald W. Hart 38 Protein O-Linked-Mannose Beta-1,2-N- Acetylglucosaminyltransferase 1 (POMGNT1) ...... 409 Hiroshi Manya and Tamao Endo

Section V N-Acetylgalactosaminyltransferases ...... 415

39 Beta-1,4 N-Acetylgalactosaminyltransferase 1,2 (B4GALNT1,2) ...... 417 Koichi Furukawa, Keiko Furukawa, Yuhsuke Ohmi, Yuki Ohkawa, Yoshio Yamauchi, Noboru Hashimoto, and Orie Tajima 40 Beta1,4-N-Acetylgalactosaminyltransferase-3 (B4GALNT3) and Beta1,4-N-Acetylgalactosaminyltransferase-4 (B4GALNT4) ...... 429 Jacques U. Baenziger 41 Beta1,3-N-Acetylgalactosaminyltransferase 2 (B3GALNT2) .... 439 Kiyohiko Angata, Takashi Sato, Akira Togayachi, and Hisashi Narimatsu 42 Beta1,3-N-Acetylgalactosaminyltransferase 1 (B3GALNT1) ...... 447 Koichi Honke 43 Globoside Alpha-1,3-N-Acetylgalactosaminyltransferase 1 (GBGT1) ...... 455 Koichi Honke Contents xix

44 Histo-Blood Group A and B , Their Gene Structures, and Common O Group Gene Structures ...... 463 Sen-itiroh Hakomori and Monica Palcic

45 Histo-Blood Group A Variants, O Variants, and Their Alleles . . 479 Sen-itiroh Hakomori and Monica Palcic

46 UDP-N-Acetyl-Alpha-D-Galactosamine: Polypeptide N-Acetylgalactosaminyltransferases (ppGalNAc-Ts) ...... 495 Liping Zhang, E. Tian, and Kelly G. Ten Hagen

Section VI ...... 513

47 Fucosyltransferases 1, 2. GDP-Fucose Galactoside a2-Fucosyltransferases. FUT1 or H Blood Group, FUT2 or ABH and Sec1 (FUT1, FUT2, Sec1) ...... 515 Rafael Oriol and Rosella Mollicone

48 3. GDP-Fucose Lactosamine a1,3/4- Fucosyltransferase. Lea and Leb Histo-Blood Groups (FUT3, Lewis Enzyme) ...... 531 Takashi Kudo and Hisashi Narimatsu

49 Fucosyltransferase 4. GDP-Fucose Lactosamine a1,3-Fucosyltransferase. Myeloid Specific (FUT4) ...... 541 Takashi Kudo and Hisashi Narimatsu

50 Fucosyltransferase 5. GDP-Fucose Lactosamine a3/4-Fucosyltransferase (FUT5) ...... 549 Reiji Kannagi

51 Fucosyltransferase 6. GDP-Fucose Lactosamine a3-Fucosyltransferase (FUT6) ...... 559 Reiji Kannagi

52 Fucosyltransferase 7. GDP-Fucose Lactosamine a1,3-Fucosyltransferase. Sialyl-Lex Specific (FUT7) ...... 573 Takashi Kudo and Hisashi Narimatsu

53 Fucosyltransferase 8. GDP-Fucose N-Glycan Core a6-Fucosyltransferase (FUT8) ...... 581 Hideyuki Ihara, Hiroki Tsukamoto, Jianguo Gu, Eiji Miyoshi, Naoyuki Taniguchi, and Yoshitaka Ikeda

54 Fucosyltransferase 9. GDP-Fucose Lactosamine a1,3-Fucosyltransferase. Lex Specific (FUT9) ...... 597 Takashi Kudo and Hisashi Narimatsu xx Contents

55 Fucosyltransferases 10, 11. GDP-Fucose N-Glycan Core a1,3-Fucosyltransferases (FUT10, FUT11) ...... 605 Rosella Mollicone and Rafael Oriol

56 Fucosyltransferases 12, 13: Protein O-Fucosyltransferases 1 and 2 (POFUT1, POFUT2) ...... 623 Shinako Kakuda and Robert S. Haltiwanger Volume 2

Section VII ...... 635

57 ST3 Beta-Galactoside Alpha-2,3- 1 (ST3GAL1) ...... 637 Kiyohiko Angata and Minoru Fukuda

58 ST3 Beta-Galactoside Alpha-2,3-Sialyltransferase 2 (ST3GAL2) ...... 645 Shuichi Tsuji and Shou Takashima

59 ST3 Beta-Galactoside Alpha-2,3-Sialyltransferase 3 (ST3GAL3) ...... 657 Ronald L. Schnaar

60 ST3 Beta-Galactoside Alpha-2,3-Sialyltransferase 4 (ST3GAL4) ...... 667 Ronald L. Schnaar

61 ST3 Beta-Galactoside Alpha-2,3-Sialyltransferase 5 (ST3GAL5) ...... 675 Jin-ichi Inokuchi and Satoshi Uemura

62 ST3 Beta-Galactoside Alpha-2,3-Sialyltransferase 6 (ST3GAL6) ...... 687 Tetsuya Okajima and Koichi Furukawa

63 ST6 Beta-Galactoside Alpha-2,6-Sialyltranferase 1 (ST6GAL1) ...... 693 Shinobu Kitazume

64 ST6 Beta-Galactoside Alpha-2,6-Sialyltranferase 2 (ST6GAL2) ...... 705 Shou Takashima and Shuichi Tsuji

65 ST6 N-Acetylgalactosaminide Alpha-2,6-Sialyltransferase 1 (ST6GALNAC1) ...... 715 Shuichi Tsuji and Shou Takashima Contents xxi

66 ST6 N-Acetylgalactosaminide Alpha-2,6-Sialyltransferase 2 (ST6GALNAC2) ...... 727 Shuichi Tsuji and Shou Takashima 67 ST6 N-Acetylgalactosaminide Alpha-2,6-Sialyltransferase 3 (ST6GALNAC3) ...... 737 Shou Takashima and Shuichi Tsuji 68 ST6 N-Acetylgalactosaminide Alpha-2,6-Sialyltransferase 4 (ST6GALNAC4) ...... 749 Shou Takashima and Shuichi Tsuji

69 ST6 N-Acetylgalactosaminide Alpha-2,6-Sialyltransferase 5,6 (ST6GALNAC5,6) ...... 759 Koichi Furukawa, Tetsuya Okajima, Akiko Tsuchida, and Keiko Furukawa

70 ST8 Alpha-N-Acetyl-Neuraminide Alpha-2,8-Sialyltransferase 1 (ST8SIA1) ...... 767 Marie Bobowski, Anne Harduin-Lepers, and Philippe Delannoy 71 ST8 Alpha-N-Acetyl-Neuraminide Alpha-2,8-Sialyltransferase 2 (ST8SIA2) ...... 781 Chihiro Sato 72 ST8 Alpha-N-Acetyl-Neuraminide Alpha-2,8-Sialyltransferase 3 (ST8SIA3) ...... 797 Shuichi Tsuji and Shou Takashima 73 ST8 Alpha-N-Acetyl-Neuraminide Alpha-2,8-Sialyltransferase 4 (ST8SIA4) ...... 805 Kiyohiko Angata and Minoru Fukuda 74 ST8 Alpha-N-Acetyl-Neuraminide Alpha-2,8-Sialyltransferase 5 (ST8SIA5) ...... 813 Shuichi Tsuji and Shou Takashima 75 ST8 Alpha-N-Acetyl-Neuraminide Alpha-2,8-Sialyltransferase 6 (ST8SIA6) ...... 823 Shou Takashima and Shuichi Tsuji

Section VIII Glucuronyltransferases ...... 833

76 Beta-1,3-Glucuronyltransferase 1 ( P); Beta-1,3-Glucuronyltransferase 2 (B3GAT1,2) ...... 835 Yasuhiko Kizuka and Shogo Oka 77 Beta-1,3-Glucuronyltransferase 3 (Glucuronosyltransferase I) (B3GAT3) ...... 849 Hiroshi Kitagawa and Satomi Nadanaka xxii Contents

Section IX GAG Polymerase and Related ...... 863

78 1-3 (HAS1-3) ...... 865 Naoki Itano, Theerawut Chanmee, and Koji Kimata 79 I, II (XYLT1,2) ...... 873 Myron E. Hinsdale 80 Exostoses (Multiple)-Like 1-3 (EXTL1-3) ...... 885 Hiroshi Kitagawa and Satomi Nadanaka 81 Exostosin 1,2 (EXT1,2) ...... 905 Hiroshi Kitagawa and Satomi Nadanaka 82 N-Acetylgalactosaminyltransferase 1,2 (CSGALNACT1,2) ...... 925 Takashi Sato and Hisashi Narimatsu

83 Dermatan Sulfate Epimerases (DSE, DSEL) ...... 935 Marco Maccarana and Anders Malmstro¨m

84 Chondroitin Polymerizing Factor, Chondroitin Polymerizing Factor 2, Chondroitin Sulfate Synthase 1,3 (CHPF, CHPF2, CHSY1, CHSY3) ...... 947 Hiroshi Kitagawa and Satomi Nadanaka

85 Heparin-Heparansulfate Related GlcA C5-Epimerase ...... 965 Jin-ping Li

Section X ...... 977

86 Carbohydrate (Chondroitin 6) Sulfotransferase 3; Carbohydrate (N-Acetylglucosamine 6-O) Sulfotransferase 7 (CHST3,7) ..... 979 Osami Habuchi

87 Carbohydrate (Keratan Sulfate Gal-6) Sulfotransferase 1 (CHST1) ...... 989 Osami Habuchi

88 Carbohydrate (N-Acetylglucosamine-6-O) Sulfotransferase 2 (CHST2) ...... 997 Kenji Uchimura 89 Carbohydrate (N-Acetylglucosamine 6-O) Sulfotransferase 5 and 6 (CHST5,6) ...... 1005 Tomoya O. Akama and Michiko N. Fukuda 90 Carbohydrate (N-Acetylglucosamine 6-O) Sulfotransferase 4 (CHST4) ...... 1015 Steven D. Rosen Contents xxiii

91 Carbohydrate (Chondroitin 4) Sulfotransferase 11-13 (CHST11-13) ...... 1025 Osami Habuchi

92 Carbohydrate Sulfotransferase 10 (CHST10) ...... 1035 Hans Bakker

93 Uronyl-2-Sulfotransferase (UST) ...... 1047 Jian Liu and Tim O’Leary

94 Heparan Sulfate 2-O-Sulfotransferase (HS2ST) ...... 1053 Hiroko Habuchi

95 Heparan-Sulfate 6-O-Sulfotransferase 1-3 (HS6ST1-3) ...... 1067 Naoko Nagai and Koji Kimata

96 Heparan Sulfate (Glucosamine) 3-O-Sulfotransferase 1-6 (HS3ST1-6) ...... 1081 Jian Liu and Tim O’Leary

97 N-Deacetylase/N-Sulfotransferase (Heparan Glucosaminyl) 1 (NDST1) ...... 1091 Kay Grobe

98 N-Deacetylase/N-Sulfotransferase (Heparan Glucosaminyl) 2 (NDST2) ...... 1105 Lena Kjelle´n

99 N-Deacetylase/N-Sulfotransferase (Heparan Glucosaminyl) 3,4 (NDST3,4) ...... 1113 Jun-ichi Aikawa

100 Galactose-3-O-Sulfotransferase 1-4 (GAL3ST1-4) ...... 1123 Koichi Honke

101 Carbohydrate (N-Acetylgalactosamine 4-O) Sulfotransferase 14 (CHST14) ...... 1135 Tomoki Kosho, Shuji Mizumoto, and Kazuyuki Sugahara

102 N-Acetylgalactosamine-4-sulfotransferase-1 (GalNAc-4-ST1, CHST8) and N-Acetylgalactosamine-4-sulfotransferase-2 (GalNAc-4-ST2, CHST9) ...... 1149 Jacques U. Baenziger

103 Carbohydrate (N-Acetylgalactosamine 4-Sulfate 6-O) Sulfotransferase 15 (CHST15) ...... 1157 Osami Habuchi xxiv Contents

Volume 3

Section XI Glycosyltransferase-like Proteins (inplicated in alpha-dystrogly) ...... 1165

104 Like-Glycosyltransferase; Glycosyltransferase-Like 1B (LARGE, GYLTL1B) ...... 1167 Kei-ichiro Inamori and Kevin P. Campbell

105 Fukutin and Fukutin-Related Protein (FKRP) ...... 1181 Motoi Kanagawa and Tatsushi Toda

Section XII GPI Anchor Biosynthesis ...... 1191

106 Glycosylphosphatidylinositol-N-Acetylglucosaminyltransferase (GPI-GlcNAc Transferase): A Complex Comprised of PIGA, PIGC, PIGH, PIGQ, PIGP, PIGY and DPM2 ...... 1193 Taroh Kinoshita, Norimitsu Inoue, and Yoshiko Murakami

107 GPI Mannose Extension (PIGM, PIGV, PIGB, PIGZ) ...... 1209 Taroh Kinoshita and Norimitsu Inoue

Section XIII N-Glycan Precursor Biosynthesis, en-bloc Transfer and Processing ...... 1221

108 Dolichyl-Phosphate (UDP-N-Acetylglucosamine) N-Acetylglucosaminephospho-transferase 1 (GlcNAc-1-P Transferase) (DPAGT1) ...... 1223 Neta Dean and Xiao-Dong Gao

109 Heterodimeric Alg13/Alg14 UDP-GlcNAc Transferase (ALG13,14) ...... 1231 Neta Dean and Xiao-Dong Gao

110 Alg1, Alg2, and Alg11 Mannosyltransferases of the ...... 1239 Neta Dean

111 ALG Mannosyltransferases, ER Lumen = Alpha Linkage (ALG3,9,12) ...... 1249 Markus Aebi

112 OST Complex (OST48, Ribophorin I, Ribophorin II, DAD1) . . . 1255 Yoichiro Harada and Tadashi Suzuki

113 Mannosyl-Oligosaccharide Glucosidase (Glucosidase I, MOGS) 1273 Alison V. Nairn and Kelley W. Moremen Contents xxv

114 Glucosidase, Alpha Neutral AB; Glucosidase II Subunit Beta (GANAB, PRKCSH, a-Glucosidase II) ...... 1283 Alison V. Nairn and Kelley W. Moremen

115 Mannosidase, Alpha, Class 1 (MAN1A1 (Golgi Alpha-Mannnosidase IA), Man1A2 (Golgi Alpha-Mannosidase IB), MAN1B1 (ER Alpha-Mannosidase I), MAN1C1 (Golgi Alpha-Mannosidase IC)) ...... 1297 Kelley W. Moremen and Alison V. Nairn

116 Mannosidase, Alpha, Class 2a1 (MAN2A1, Golgi a-Mannosidase II) ...... 1313 Kelley W. Moremen and Alison V. Nairn 117 Mannosidase, Alpha, Class 2a2 (MAN2A2) ...... 1327 Michiko N. Fukuda, Kazuhiro Sugihara, and Tomoya O. Akama 118 N-Acetylglucosamine-1-Phosphate Transferase, Alpha/Beta and Gamma Subunits (GNPTAB, GNPTG) ...... 1335 Maria Francisca Coutinho 119 N-Acetylglucosamine-1-Phosphodiester Alpha-N- Acetylglucosaminidase (NAGPA) ...... 1349 Stuart Kornfeld

Section XIV Nucleotide Sugar Transporters ...... 1359

120 Solute Carrier Family 35 (UDP-Galactose Transporter), Member A2 (SLC35A2) ...... 1361 Nobuhiro Ishida 121 Solute Carrier Family 35 (CMP-Sialic Acid Transporter), Member A1 (SLC35A1) ...... 1369 Shoko Nishihara 122 Adenosine 30-Phospho 50-Phosphosulfate Transporter 1,2 (PAPST1,2) (SLC35B2,3) ...... 1379 Shoko Nishihara 123 UDP-Xylose and UDP-N-Acetylglucosamine Transporter (SLC35B4) ...... 1393 Hans Bakker and Angel Ashikov 124 GDP-Fucose Transporter 1 (SLC35C1) ...... 1403 Hans Bakker, Angel Ashikov, Francoise H. Routier, and Rita Gerardy-Schahn 125 UDP-N-Acetylglucosamine/UDP-Glucose/GDP-Mannose Transporter (HFRC1) (SLC35D2) ...... 1413 Shoko Nishihara xxvi Contents

Section XV Transferase Donor Substrate Biosynthesis and Related Reactions ...... 1423

126 UDP-Glucose 6-Dehydrogenase (UGDH) ...... 1425 Yanusz Wegrowski and Andrew A. Pitsillides

127 UDP-Glucuronate Decarboxylase 1 (UXS1) ...... 1439 Hans Bakker

128 UDP-Galactose-4-Epimerase (GALE) ...... 1449 Thomas J. McCorvie and David J. Timson

129 Glutamine–Fructose-6-Phosphate Transaminase 1,2 (GFPT1,2) ...... 1465 Kazuto Yamazaki

130 Glucosamine-6 Phosphate N-Acetyltransferase (GNPNAT1 / GNA1) ...... 1481 James W. Dennis

131 N-Acetylglucosamine Kinase (NAGK) ...... 1489 Markus Berger and Stephan Hinderlich

132 Phosphoglucomutase 3 (= Phosphoacetylglucosamine Mutase) (PGM3) ...... 1497 Hisafumi Okabe and Toshiyuki Mio

133 UDP-N-Acetylglucosamine Pyrophosphorylase 1 (UAP1) ...... 1503 Hisafumi Okabe and Toshiyuki Mio

134 UDP-GlcNAc 2-Epimerase/ManNAc Kinase (GNE) ...... 1511 Werner Reutter, Stephan Hinderlich, and Wolfgang Kemmner

135 N-Acetylneuraminic Acid Synthase (NANS) ...... 1523 Michael J. Betenbaugh, Bojiao Yin, Emily Blake, Linda Kristoffersen, Someet Narang, and Karthik Viswanathan

136 N-Acetylneuraminic Acid Phosphatase (NANP) ...... 1537 Ken Kitajima

137 Cytidine Monophosphate N-Acetylneuraminic Acid Synthetase (CMAS) ...... 1545 Birgit Weinhold, Rita Gerardy-Schahn, and Anja Munster-K€ uhnel€ 138 Cytidine Monophospho-N-Acetylneuraminic Acid Hydroxylase (CMAH) ...... 1559 Anne K. Bergfeld and Ajit Varki 139 Mannose Phosphate Isomerase (MPI) ...... 1581 Vandana Sharma and Hudson Freeze Contents xxvii

140 Phosphomannomutase 1,2 (PMM1,2) ...... 1591 Vandana Sharma and Hudson Freeze 141 GDP-Mannose Pyrophosphorylase A,B (GMPPA,B) ...... 1599 Hiroto Hirayama and Tadashi Suzuki 142 Tissue Specific Transplantation P35B (= GDP-4-keto- 6-D-Deoxymannose Epimerase-Reductase) (TSTA3) ...... 1607 Michela Tonetti 143 Fucokinase (FUK) ...... 1623 Stephan Hinderlich and Stefan Reinke 144 Fucose-1-Phosphate Guanylyltransferase (FPGT) ...... 1631 Risto Renkonen 145 Dolichyl-Phosphate Polypeptide (DPM1-3) ...... 1637 Tetsuo Takahashi 146 Dolichyl-Phosphate Beta-Glucosyltransferase (ALG5) ...... 1649 Tetsuo Takahashi

Appendix ...... 1657

147 Map 1: Biosynthetic Pathways of N-Glycans ...... 1659 Akira Seko and Katsuko Yamashita 148 Map 2: Biosynthetic Pathways of O-Glycans ...... 1667 Hiroshi Nakada 149 Map 3: Biosynthetic Pathways of Glycosphingolipids ...... 1673 Jin-ichi Inokuchi and Shinji Go 150 Map 4: Biosynthetic Pathways of Proteoglycans ...... 1681 Pawared Ontong, Theerawut Chanmee, and Naoki Itano 151 Map 5: Biosynthetic Pathways of GPI-Anchor ...... 1687 Norimitsu Inoue and Taroh Kinoshita

Index ...... 1693

Contributors

Markus Aebi Institut f. Mikrobiologie, ETH Zurich,€ Zurich,€ Switzerland Jun-ichi Aikawa Synthetic Cellular Chemistry Laboratory, RIKEN, Saitama, Japan Tomoya O. Akama Department of Pharmacology, Kansai Medical University, Hirakata, Osaka, Japan Sanford-Burnham Medical Research Institute, La Jolla, CA, USA Kiyohiko Angata Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan Angel Ashikov Institute for Cellular Chemistry, Hannover Medical School, Hannover, Germany Jacques U. Baenziger Biology and Biomedical Sciences, Washington University in St. Louis, St. Louis, MO, USA Hans Bakker Institute for Cellular Chemistry, Hannover Medical School, Hannover, Germany Partha Banerjee Department of Biological Chemistry, Johns Hopkins School of Medicine, Baltimore, MD, USA Brad Bendiak Anschutz Medical Campus, University of Colorado, Aurora, CO, USA Markus Berger Glycodesign and Glycoanalytics, Charite´ - University Medicine Berlin, Central Institute of Laboratory Medicine, Clinical Chemistry and Pathobiochemistry, Berlin, Germany Anne K. Bergfeld Department of Cellular and Molecular Medicine, University of California, San Diego, La Jolla, CA, USA Michael J. Betenbaugh Department of Chemical and Biomolecular Engineering, Johns Hopkins University, Baltimore, MD, USA Emily Blake Department of Chemical and Biomolecular Engineering, Johns Hopkins University, Baltimore, MD, USA

xxix xxx Contributors

Marie Bobowski Structural and Functional Glycobiology Unit, University of Sciences and Technologies of Lille, UMR CNRS 8576, Villeneuve d’ Ascq, France Kevin P. Campbell Howard Hughes Medical Institute, Department of Molecular Physiology and Biophysics, University of Iowa Roy J. and Lucille A. Carver College of Medicine, Iowa City, IA, USA Julio J. Caramelo Fundacio´n Instituto Leloir, Buenos Aires, Argentina Theerawut Chanmee Department of Molecular Biosciences, Faculty of Life Sciences, Kyoto Sangyo University, Kita-Ku, Kyoto, Japan Dale Christiansen Department of Surgery, Austin Health/Northern Health, The University of Melbourne, Heidelberg, VIC, Australia Henrik Clausen Copenhagen Center for Glycomics, Department of Cellular and Molecular Medicine, University of Copenhagen, Institute of Health Science, Copenhagen N, Denmark Maria Francisca Coutinho Department of Human Genetics, National Health Institute Doutor Ricardo Jorge, IP, Porto, Portugal Richard D. Cummings Department of Biochemistry, Emory University School of Medicine, Atlanta, GA, USA Cecilia D’Alessio Fundacio´n Instituto Leloir, Buenos Aires, Argentina Neta Dean Department of Biochemistry and Cell Biology, Stony Brook Univer- sity, Stony Brook, NY, USA Philippe Delannoy Structural and Functional Glycobiology Unit, University of Sciences and Technologies of Lille, UMR CNRS 8576, Villeneuve d’ Ascq, France James W. Dennis Joseph and Wolf Lebovic Health Complex, Lunenfeld- Tanenbaum Research Institute, Mount Sinai Hospital, Toronto, ON, Canada Tamao Endo Molecular Glycobiology, Tokyo Metropolitan Geriatric Hospital and Institute of Gerontology, Itabashi-ku, Tokyo, Japan Hudson Freeze Sanford-Burnham Medical Research Institute, La Jolla, CA, USA Michiko N. Fukuda Sanford-Burnham Medical Research Institute, La Jolla, CA, USA Minoru Fukuda Sanford Burnham Medical Research Institute, La Jolla, CA, USA Keiko Furukawa Department of Biomedical Sciences, Chubu University College of Life and Health Sciences, Kasugai, Japan Kiyoshi Furukawa Department of Bioengineering, Nagaoka University of Technology, Niigata, Japan Contributors xxxi

Koichi Furukawa Department of Biochemistry II, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya, Japan Xiao-Dong Gao The Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, Jiangsu Province, China Rita Gerardy-Schahn Institute for Cellular Chemistry, Hannover Medical School, Hannover, Germany Shinji Go Division of Glycopathology, Tohoku Pharmaceutical University, Insti- tute of Molecular Biomembranes and Glycobiology, Sendai, Miyagi, Japan Kay Grobe Institute for Physiological Chemistry and Pathobiochemistry, University Hospital Munster,€ Westf€alische Wilhelms-Universit€at Munster,€ Munster,€ Germany Jianguo Gu Division of Regulatory Glycobiology, Institute of Molecular Biomembrane and Glycobiology, Tohoku Pharmaceutical University, Aoba-ku, Sendai Miyagi, Japan Hiroko Habuchi Aichi Medical University, Nagakute, Aichi, Japan Osami Habuchi Advanced Medical Research Center, Aichi Medical University, Nagakute, Aichi, Japan Sen-itiroh Hakomori Division of Biomembrane Research, Pacific Northwest Research Institute Departments of Microbiology and Pathobiology, University of Washington, Seattle, WA, USA Robert S. Haltiwanger Department of Biochemistry and Cell Biology, Stony Brook University, Stony Brook, NY, USA Lars Hansen Copenhagen Center for Glycomics, Department of Cellular and Molecular Medicine, University of Copenhagen, Institute of Health Science, Copenhagen N, Denmark Yoichiro Harada Glycometabolome Team, Systems Glycobiology Research Group, RIKEN-Max Planck Joint Research Center, Global Research Cluster, RIKEN, Wako, Saitama, Japan Anne Harduin-Lepers Structural and Functional Glycobiology Unit, University of Sciences and Technologies of Lille, UMR CNRS 8576, Villeneuve d’ Ascq, France Gerald W. Hart Department of Biological Chemistry, Johns Hopkins School of Medicine, Baltimore, MD, USA Noboru Hashimoto Department of Biochemistry II, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya, Japan xxxii Contributors

Stephan Hinderlich Department of Life Sciences and Technology, Beuth Hochschule fur€ Technik Berlin - University of Applied Sciences, Berlin, Germany

Myron E. Hinsdale Oklahoma State University, Stillwater, OK, USA Yoshio Hirabayashi Molecular Membrane Neuroscience, RIKEN Brain Science Institute, Wako, Saitama, Japan

Hiroto Hirayama Glycometabolome Team, Systems Glycobiology Research Group, RIKEN-Max Planck Joint Research Center, Global Research Cluster, RIKEN, Wako, Saitama, Japan

Koichi Honke Department of Biochemistry, Kochi University Medical School, Nankoku, Kochi, Japan

Hideyuki Ihara Division of Molecular Cell Biology, Department of Biomolecular Sciences, Faculty of Medicine, Saga University, Saga, Japan

Yoshitaka Ikeda Division of Molecular Cell Biology, Department of Biomolecular Sciences, Faculty of Medicine, Saga University, Saga, Japan

Kei-ichiro Inamori Division of Glycopathology, Institute of Molecular Biomembrane and Glycobiology, Tohoku Pharmaceutical University, Sendai, Miyagi, Japan

Jin-ichi Inokuchi Division of Glycopathology, Tohoku Pharmaceutical University, Institute of Molecular Biomembranes and Glycobiology, Sendai, Miyagi, Japan

Norimitsu Inoue Department of Molecular Genetics, Osaka Medical Center for Cancer and Cardiovascular Diseases, Osaka, Japan

Yohei Ishibashi Molecular Membrane Neuroscience, RIKEN Brain Science Insti- tute, Wako, Saitama, Japan

Nobuhiro Ishida Department of Environmental Security System, Chiba Institute of Science, Choshi, Chiba, Japan

Naoki Itano Department of Molecular Biosciences, Faculty of Life Sciences, Kyoto Sangyo University, Kita-Ku, Kyoto, Japan

Tongzhong Ju Department of Biochemistry, Emory University School of Medicine, Atlanta, GA, USA

Shinako Kakuda Department of Biochemistry and Cell Biology, Stony Brook University, Stony Brook, NY, USA

Motoi Kanagawa Department of Physiology and Cell Biology, Division of Molecular Brain Science, Kobe University, Graduate School of Medicine, Chuo-ku, Kobe, Japan Contributors xxxiii

Reiji Kannagi Advanced Medical Research Center, Aichi Medical University, Nagakute, Aichi, Japan Wolfgang Kemmner Charite - Universit€atsmedizin Berlin, Experimental and Clinical Research Center, Berlin, Germany Koji Kimata Advanced Medical Research Center, Aichi Medical University, Nagakute, Aichi, Japan Taroh Kinoshita Department of Immunoregulation, Research Institute for Micro- bial Diseases, Osaka University, Suita, Osaka, Japan Hiroshi Kitagawa Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, Kobe, Japan Ken Kitajima Biosecience and Biotechnology Center, Nagoya University, Chikusa-ku, Nagoya, Japan Shinobu Kitazume Disease Glycomics Team, Systems Glycobiology Research Group, RIKEN, Saitama, Japan Yasuhiko Kizuka Disease Glycomics Team, RIKEN-Max Planck Joint Research Center, RIKEN, Wako, Japan Lena Kjelle´n Department of Medical Biochemistry and Microbiology, Uppsala University, BMC, Uppsala, Sweden Yuji Kondo Department of Biochemistry II, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya, Japan Stuart Kornfeld Department of Internal Medicine, Washington University School of Medicine, St. Louis, MO, USA Tomoki Kosho School of Medicine, Department of Medical Genetics, Shinshu University, Matsumoto, Japan Linda Kristoffersen Department of Chemical and Biomolecular Engineering, Johns Hopkins University, Baltimore, MD, USA Takashi Kudo University of Tsukuba, Tsukuba, Japan Jin-ping Li The Biomedical Center, Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden Jian Liu Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC, USA Marco Maccarana Department of Experimental Medical Science, Lund Univer- sity, Lund, Sweden Akira Maeda Division of Organ Transplantation, Department of Surgery, Osaka University Graduate School of Medicine, Osaka, Japan xxxiv Contributors

Anders Malmstro¨m Department of Experimental Medical Science, Lund University, Lund, Sweden Hiroshi Manya Molecular Glycobiology, Tokyo Metropolitan Geriatric Hospital and Institute of Gerontology, Itabashi-ku, Tokyo, Japan Thomas J. McCorvie Medical Biology Centre, Queen’s University Belfast, School of Biological Sciences, Belfast, UK Toshiyuki Mio Research Division, Chugai Pharmaceutical Co. LTD, Kamakura, Kanagawa, Japan Shuji Miyagawa Division of Organ Transplantation, Department of Surgery, Osaka University Graduate School of Medicine, Osaka, Japan Eiji Miyoshi Department of Molecular Biochemistry and Clinical Investigation, Osaka University Graduate School of Medicine, Suita, Japan Shuji Mizumoto Laboratory of Signaling and Therapeutics, Hokkaido University Graduate School of Life Science, Kita-ku, Sapporo, Japan Rosella Mollicone Reponses cellulaires au microenvironement et cancer, CNRS and INSERM U1004, Villejuif, France Kelley W. Moremen Complex Carbohydrate Research Center, The University of Georgia, Athens, GA, USA Effie Mouhtouris Department of Surgery, Austin Health/Northern Health, The University of Melbourne, Heidelberg, VIC, Australia Anja Munster-K€ uhnel€ Institute for Cellular Chemistry, Hannover Medical School, Hannover, Germany Yoshiko Murakami Department of Immunoregulation, Research Institute for Microbial Diseases, Osaka University, Suita, Osaka, Japan Satomi Nadanaka Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, Kobe, Japan Naoko Nagai Institute for Molecular Science of Medicine, Aichi Medical University, Nagakute, Aichi, Japan Alison V. Nairn Complex Carbohydrate Research Center, The University of Geor- gia, Athens, GA, USA Hiroshi Nakada Department of Molecular Sciences, Faculty of Life Sciences, Kyoto Sangyo University, Kamigamo-Motoyama, Kita-ku, Kyoto, Japan Jun Nakayama Department of Molecular Pathology, Shinshu University Graduate School of Medicine, Matsumoto, Japan Someet Narang MedImmune, Gaithersburg, MD, USA Contributors xxxv

Hisashi Narimatsu Research Center for Medical Glycoscience (RCMG), National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan Shoko Nishihara Department of Bioinformatics, Faculty of Engineering, Soka University, Hachioji, Tokyo, Japan Yuki Ohkawa Department of Biochemistry II, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya, Japan Yuhsuke Ohmi Department of Biochemistry II, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya, Japan Kazuaki Ohtsubo Department of Analytical Biochemistry, School of Health Sciences, Kumamoto University, Kumamoto, Japan Shogo Oka Department of Biological Chemistry, Human Health Sciences, Graduate School of Medicine, Kyoto University, Kyoto, Japan Hisafumi Okabe Chugai Pharmaceutical Co. LTD, Kamakura, Kanagawa, Japan Tetsuya Okajima Department of Biochemistry II, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya, Japan Tim O’Leary Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC, USA Pawared Ontong Department of Molecular Biosciences, Faculty of Life Sciences, Kyoto Sangyo University, Kita-Ku, Kyoto, Japan Rafael Oriol Inserm U1004 Reponses cellulaires au microenvironement et cancer, CNRS et L’Universite´ de Paris Sud XI, Villejuif, France Monica Palcic Carlsberg Laboratory, Copenhagen V, Denmark Armando J. Parodi Fundacio´n Instituto Leloir, Buenos Aires, Argentina Michael Pierce Department of Biochemistry and Molecular Biology, Complex Carbohydrate Research Center, The University of Georgia, Athens, GA, USA Andrew A. Pitsillides Department of Veterinary Basic Sciences, Royal Veterinary College, London, England, UK Pradman K. Qasba CCR Nanobiology Program, National Cancer Institute- Frederick, NIH, Frederick, MD, USA Boopathy Ramakrishnan Structural Glycobiology Section, Nanobiology Program, and Basic Research Program, Frederick National Laboratory for Cancer Research, SAIC-Frederick, Inc., Center for Cancer Research, Frederick, MD, USA Stefan Reinke Department of Life Sciences and Technology, Beuth Hochschule fur€ Technik Berlin – University of Applied Sciences, Berlin, Germany xxxvi Contributors

Risto Renkonen Haartman Institute, University of Helsinki, Helsinki, Finland Werner Reutter Institute of Biochemistry and Molecular Biology, Charite´ - Universit€atsmedizin Berlin, Berlin-Dahlem, Germany Steven D. Rosen Department of Anatomy, University of California, San Fransisco, San Francisco, CA, USA Francoise H. Routier Institute for Cellular Chemistry, Hannover Medical School, Hannover, Germany Mauro S. Sandrin Department of Surgery, Austin Health/Northern Health, The University of Melbourne, Heidelberg, VIC, Australia Chihiro Sato Bioscience and Biotechnology Center, Nagoya University, Nagoya, Japan Takashi Sato Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan Ronald L. Schnaar Departments of Pharmacology and Neuroscience, Johns Hopkins University School of Medicine, Baltimore, MD, USA Akira Seko JST, ERATO, Wako, Saitama, Japan Vandana Sharma Sanford-Burnham Medical Research Institute, La Jolla, CA, USA Pamela Stanley Department of Cell Biology, Albert Einstein College of Medi- cine, New York, NY, USA Kazuyuki Sugahara Laboratory of Proteoglycan Signaling and Therapeutics, Hokkaido University Graduate School of Life Science, Kita-ku, Sapporo, Japan Kazuhiro Sugihara Department of Obsteterics and Gynecology, Haamamatsu University School of Medicine, Hamamatsu City, Shizuoka, Japan Misa Suzuki-Anekoji Tumor Microenvironment Program, Sanford-Burnham Medical Research Institute, La Jolla, CA, USA Tadashi Suzuki Glycometabolome Team, Systems Glycobiology Research Group, RIKEN-Max Planck Joint Research Center, Global Research Cluster, RIKEN, Wako, Saitama, Japan Tomohiko Taguchi Laboratory of Pathological Cell Biology, Graduate School of Pharmaceutical Sciences, University of Tokyo, Tokyo, Japan Orie Tajima Department of Biomedical Sciences, Chubu University College of Life and Health Sciences, Kasugai, Japan Tetsuo Takahashi Department of Applied Biochemistry, School of Engineering, Tokai University, Hiratsuka, Kanagawa, Japan Contributors xxxvii

Shou Takashima Laboratory of Glycobiology, The Noguchi Institute, Itabashi, Tokyo, Japan Hideyuki Takeuchi Department of Biochemistry and Cell Biology, Stony Brook University, Stony Brook, NY, USA Naoyuki Taniguchi RIKEN-Max-Planck Joint Research Center for Systems Chemical Biology, RIKEN, Wako, Saitama, Japan Kelly G. Ten Hagen NIDCR/National Institutes of Health, Bethesda, MD, USA E. Tian NIDCR/National Institutes of Health, Bethesda, MD, USA David J. Timson Queen’s University, Belfast, UK Tatsushi Toda Department of Neurology / Department of Physiology and Cell Biology, Division of Molecular Brain Science, Kobe University, Graduate School of Medicine, Chuo-ku, Kobe, Japan Akira Togayachi Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan Michela Tonetti Department of Experimental Medicine, University of Genova, Genoa, Italy Shigeru Tsuboi Department of Cancer Immunology and Cell Biology, Oyokyo Kidney Research Institute, Hirosaki, Aomori, Japan Akiko Tsuchida Department of Biochemistry II, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya, Japan Shuichi Tsuji Institute of Glycoscience, Tokai University, Hiratsuka, Kanagawa, Japan Hiroki Tsukamoto Division of Molecular Cell Biology, Department of Biomolecular Sciences, Faculty of Medicine, Saga University, Saga, Japan Kenji Uchimura Department of Biochemistry, Nagoya University Graduate School of Medicine, Nagoya, Aichi, Japan Satoshi Uemura Molecular Genetic Research Department of Chemistry and Biological Science, Aoyama Gakuin University, College of Science and Engineering, Sagamihara, Japan Ajit Varki Department of Cellular and Molecular Medicine, University of California, San Diego, La Jolla, CA, USA Malene Bech Vester-Christensen Copenhagen Center for Glycomics, Department of Cellular and Molecular Medicine, University of Copenhagen, Institute of Health Science, Copenhagen N, Denmark Karthik Viswanathan Department of Biological Engineering, Massachusetts Institute of Technology, Cambridge, MA, USA xxxviii Contributors

Yanusz Wegrowski Laboratoire de Biochimie Me´dicale et Biologie Mole´culaire, Universite´; de Reims, Reims, Champagne-Ardenne, France Birgit Weinhold Institute for Cellular Chemistry, Hannover Medical School, Hannover, Germany Katsuko Yamashita Department of History and Cell Biology, School of Medicine, Yokohama City University, Yokohama, Japan Yoshio Yamauchi Department of Biochemistry II, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya, Japan Kazuto Yamazaki Tsukuba Research Laboratories, Eisai Co., Ltd, Tsukuba, Ibaraki, Japan Jiunn-Chern (Gene) Yeh Tumor Microenvironment Program, Sanford-Burnham Medical Research Institute, La Jolla, CA, USA Bojiao Yin Department of Chemical and Biomolecular Engineering, Johns Hopkins University, Baltimore, MD, USA Liping Zhang NIDCR/National Institutes of Health, Bethesda, MD, USA