26th International Carbohydrate Symposium (ICS 2012) Madrid, Spain 22-27 July 2012 Volume 1 of 2 ISBN: 978-1-62993-037-4 Printed from e-media with permission by: Curran Associates, Inc. 57 Morehouse Lane Red Hook, NY 12571 Some format issues inherent in the e-media version may also appear in this print version. Copyright© (2012) by Vibo Congresos All rights reserved. Printed by Curran Associates, Inc. (2013) For permission requests, please contact Vibo Congresos at the address below. Vibo Congresos Calle Francisca Delgado 9,5 28108 Alcobendas Madrid Spain Phone: 34 91 196 76 54 Fax: 34 91 196 76 64 [email protected] Additional copies of this publication are available from: Curran Associates, Inc. 57 Morehouse Lane Red Hook, NY 12571 USA Phone: 845-758-0400 Fax: 845-758-2634 Email: [email protected] Web: www.proceedings.com TABLE OF CONTENTS VOLUME 1 PLENARY / INVITED SPEAKERS WHISTLER LECTURE - EMPIRICAL APPROACH TO UNDERSTAND GLYCOSYLATION REACTIONS AS BASIS FOR AUTOMATED OLIGOSACCHARIDE SYNTHESIS............................................................................................................1 Peter H. Seeberger PLE01 SYNTHETIC CHALLENGES AND RESEARCH OPPORTUNITIES AROUND GLYCOCONJUGATES...........................2 Y. Ito PLE02 HEPARIN: STRUCTURE, ACTIVITY AND SYNTHESIS ............................................................................................................3 R. J. Linhardt PLE03 (POLY)SIALOGLYCOTOPES IN ORGANOGENESIS.................................................................................................................4 A. K. Munster-Kuhnel, B. Weinhold, M. Muhlenhoff, H. Hildebrandt, R. Gerardy-Schahn PLE04 GALACTOFURANOSE INCORPORATION FROM MYCOBACTERIA TO WORMS ..........................................................5 Laura L. Kiessling PLE05 SWEET-TALK BETWEEN PATHOGENS AND HOSTS – FROM STRUCTURAL GLYCOBIOLOGY TO ANTIADHESIVE STRATEGIES..............................................................................................................................................................6 A. Imberty PLE06 INVESTIGATING CARBOHYDRATE-PROTEIN INTERACTIONS USING MASS SPECTROMETRY............................7 John Klassen PLE07 ENZYMATIC SYNTHESIS OF POLYSACCHARIDES IN LACTOBACILLI ..........................................................................8 Lubbert Dijkhuizen PLE08 FUNCTIONAL GLYCANS AND GLYCOCONJUGATES OF HUMAN MILK.......................................................................10 Bernd Stahl PLE09 THE CHEMICAL GLYCOBIOLOGY OF MICROBIAL PATHOGEN INTERACTIONS....................................................12 Mark Von Itzstein INV01 SYNTHETIC GLYCOCHEMISTRY: CONTROLLING SELECTIVITY WITH IRON SALTS............................................13 Jean-Marie Beau INV02 CONGENITAL DISORDERS OF GLYCOSYLATION (CDG): A BOOMING DISEASE FAMILY .....................................14 Jaak Jaeken INV03 GAGOMIC : SYNTHETIC TRICKS, MIMETICS FOR ANALYTICS AND FUTUR(ISTIC) THERAPEUTICS.............................................................................................................................................................................................15 David Bonnaffe INV04 FROM LECTIN STRUCTURE TO FUNCTIONALITY: THE SUGAR CODE AT WORK ...................................................16 H. J. Gabius, D. Solis, A. Romero, M. Menendez, J. Kopitz, S. Andre, J. Jimenez-Barbero INV05 STEREOSELECTIVE GLYCOSYLATION AND ITS USE IN THE SYNTHESIS OF CARBOHYDRATES AND NATURAL PRODUCTS .................................................................................................................................17 Jimei Ma, Rujee Lorpitthaya, Jing Zeng, Feiqing Ding, Kishan Gorpityala, Min Li Leow, Xuewei Liu INV06 ROLE OF PROTEIN O-MANNOSYLATION IN CONGENITAL MUSCULAR DYSTROPHIES........................................18 T. Endo INV07 THREE-DIMENSIONAL INTERPRETATION OF HEPARAN SULFATE SEQUENCES ....................................................19 Mark Forster, Barbara Mulloy INV08 NOVEL POLYSACCHARIDE ARCHITECTURES: CHAIN COMPACTION AND HYPERBRANCHING .....................................................................................................................................................................................20 B. E. Christensen INV09 OLIGOSACCHARIDE SYNTHESIS BY DONOR PREACTIVATION PROTOCOL .............................................................21 Xin-Shan Ye INV10 TO FIX NATURE'S MISTAKES: REPAIRING HUMAN FAULTY GENES BY SUGARS-BASED SMALL MOLECULES ...................................................................................................................................................................................22 T. Baasov INV11 CHEMICAL BIOLOGY OF HEPARAN SULFATES – FROM INSIGHTS TO APPLICATIONS ........................................23 J. E. Turnbull INV12 GLYCOMICS AND DRUG DISCOVERY.......................................................................................................................................24 Shin-Ichiro Nishmura INV13 THE GOLD(I)-CATALYZED GLYCOSYLATION WITH GLYCOSYL ORTHO- ALKYNYLBENZOATES AS DONORS .......................................................................................................................................................25 Biao Yu INV14 TOWARDS LIPOPOLYSACCHARIDE-BASED CONJUGATE VACCINES BASED ON SYNTHETIC OLIGOSACCHARIDES .................................................................................................................................................................................26 J. L. Bouissiere, A. Cordeiro Machado, K. Daragics, H. Horan, B. Richichi, S. Oscarson INV15 DIVERSITY OF CARBOHYDRATE BINDING SITES IN β-PRISM FOLD LECTINS..........................................................27 Avadhesha Surolia INV16 FUNCTIONALIZED NANOPARTICLE FOR PROTEIN ENRICHMENT AND CELL TARGETING ...............................29 Chun-Cheng Lin INV17 STEREOSELECTIVE REACTIONS OF OXOCARBENIUM IONS: CONFORMATIONAL ANALYSIS, STEREOELECTRONIC EFFECTS, AND REACTIVITY ........................................................................................................................30 Keith Allen Woerpel INV18 MICROBIAL GLYCOCONJUGATES AS ELICITORS AND SUPPRESSORS OF EUKARYOTIC INNATE IMMUNITY .....................................................................................................................................................................................31 A. Molinaro INV19 NMR STUDIES ON CARBOHYDRATE STRUCTURE AND THEIR INTERACTIONS WITH PROTEINS, A DYNAMIC PERSPECTIVE.................................................................................................................................................32 C. Guzzi, J. Angulo, I. Sutkeviciute, N. Varga, R. Ribeiro-Viana, D. Doknic, J. J. Reina, S. Sattin, M. Thepaut, F. Fieschi, A. Bernardi, J. Rojo, P. M. Nieto INV20 FROM SUPRAMOLECULAR STRUCTURE AND DYNAMICS TO BIOLOGICAL FUNCTIONS OF CARBOHYDRATE-RICH CELLULAR COATS – LESSONS LEARNED FROM BIOMIMETIC MODEL SYSTEMS..........................................................................................................................................................................................................33 Ralf P. Richter INV21 RECENT DEVELOPMENTS IN SUGAR MIMICKRY: NEW FLUOROCARBASUGARS AND IMINOSUGARS ...............................................................................................................................................................................................34 Matthieu Sollogoub INV22 SYNTHETIC CARBOHYDRATES AND VACCINES: THE CHALLENGE OF DEFEATING BACILLARY DYSENTERY ..........................................................................................................................................................................35 L. A. Mulard INV23 SYNTHETIC LECTINS: BIOMIMETIC RECEPTORS FOR CARBOHYDRATES IN WATER..........................................36 A. P. Davis INV24 SYNTHESIS AND APPLICATIONS OF GLYCONANOMATERIALS .....................................................................................38 O. Ramstrom INV25 ARRAY BASED GLYCOMICS: TOOLS AND APPLICATIONS...............................................................................................39 Niels-Christian Reichardt INV26 SYNTHETIC CORE AND LIPID A DERIVATIVES AS BIO-MOLECULAR PROBES FOR LPS- PROTEIN INTERACTIONS..........................................................................................................................................................................40 P. Kosma INV27 ON THE USE OF 1H-1H, 13C-1H AND 13C-13C NMR SPIN-COUPLINGS IN METHYL [13C]IDOHEXOPYRANOSIDES TO INVESTIGATE CONFORMATIONAL FLEXIBILITY IN SOLUTION ...............................41 Bidisha Basu, Wenhui Zhang, Ian Carmichael, Anthony S. Serianni INV28 CATALYTIC MECHANISMS OF GLYCOSYLTRANSFERASES. INSIGHT FROM QM/MM CALCULATIONS............................................................................................................................................................................................42 Igor Tvaroska INV29 CHEMICAL BIOLOGY OF O-GLCNAC - ENZYME MECHANISM TO ROLES IN DISEASE..........................................43 David Vocadlo INV30 CARBOHYDRATE MANIPULATION OF THE HUMAN GUT MICROBIOME....................................................................44 R. A. Rastall INV31 NUCLEIC ACID ENCODING TO PROGRAM THE ASSEMBLY OF GLYCAN FRAGMENTS WITH CONTROLLED GEOMETRY.......................................................................................................................................................................46