DOCSLIB.ORG

The Chemistry of L-Ascorbic Acid Derivatives in the Asymmetric Synthesis of C2- and C3- Substituted Aldono-Γ-Lactones

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
The Chemistry of L-Ascorbic Acid Derivatives in the Asymmetric Synthesis of C2- and C3- Substituted Aldono-Γ-Lactones The Chemistry of L-Ascorbic Acid Derivatives in the Asymmetric Synthesis of C2- and C3- Substituted Aldono-γ-lactones A Dissertation by Ayodele O. Olabisi M. S., Wichita State University, 2004 B. S., Wichita State University, 1999 Submitted to the College of Liberal Arts and Sciences and the Faculty of the Graduate School of Wichita State University in partial fulfillment of the requirements for the Degree of Doctor of Philosophy August 2005 The Chemistry of L-Ascorbic Acid Derivatives in the Asymmetric Synthesis of C2- and C3- Substituted Aldono-γ-lactones I have examined the final copy of this dissertation for form and content and recommend that it be accepted in partial fulfillment of the requirements for the degree of Doctor of Philosophy, with a major in Chemistry. ______________________________________ Professor Kandatege Wimalasena, Committee Chair We have read this dissertation and recommend its acceptance: __________________________________________ Professor William C. Groutas, Committee Member __________________________________________ Professor Ram P. Singhal, Committee Member __________________________________________ Professor Francis D’Souza, Committee Member __________________________________________ Professor George R. Bousfield, Committee Member Accepted for the College of Liberal Arts and Sciences __________________________________________ Dr. William Bischoff, Dean Accepted for the Graduate School __________________________________________ Dr. Susan K. Kovar, Dean ii DEDICATION To My Parents iii ACKNOWLEDMENTS I wish to express my deepest and sincerest appreciation to my advisor, Dr Kandatege Wimalasena for his positive guidance, enlightened mentoring and encouragement. His passion for the subject matter has greatly improved my knowledge and interest. My sincere appreciation extends to Dr. Shyamali Wimalasena and Dr. Mathew Mahindaratne, who helped me with my initial research training and their assistance in the preparation of my manuscripts. I would also like to give my appreciation to my other committee members; Dr. William C. Groutas, Dr. Ram Singhal, Dr. Francis D’Souza and Dr. George Bousfield for their significant recommendations. I wish to express my heartfelt gratitude to my colleagues, Dr. Srimevan Wanduragala, Dr. Mehul Bhakta, Dr. Rohan Perera and Samantha Ranaweera, for their invaluable friendship. It was a joy to work with them. Finally, I acknowledge some of the many people without whom I could not have completed my education; my wife, Monica, and children, Angela, Dominique and Folade for their love, support and encouragement even at times of difficulty. My special gratitude deeply extends to my parents and sisters for their incomparable love, support and prayers. This work was supported by a grant from the National Institutes of Health (NS 39423). iv ABSTRACT The antioxidant and redox properties of L-ascorbic acid are closely associated with the electron rich 2, 3-enediol moiety of the molecule and therefore selective functionalization of the 2- and 3-OH groups is essential for the detailed structure-activity studies. Reactions of 5- and 6-OH protected ascorbic acid with electrophilic reagents exclusively produce the corresponding 3-O-alkylated products under mild basic conditions due to the high nucleophilicity of the C-3-OH. Based on the density functional theory (B3LYP) electron density calculations, a novel and general method was devised for the direct alkylation of the 2-OH group of ascorbic acid with complete regio- and chemo-selectivity. A complete spectroscopic analysis of two complementary series of 2- O-acetyl-3-O-alkyl and 2-O-alkyl-3-O-acetyl ascorbic acid derivatives was carried out to define their spectroscopic characteristics and to resolve common inconsistencies in the literature. The asymmetric approach to the synthesis of natural products or other biologically active compounds is impeded by low abundance of natural sources as well as a limited number of efficient synthetic methods. Nevertheless, carbohydrate-based systems such as the aldono-1,4-lactones (also known as aldono-γ-lactones) which generate a host of chiral compounds have been particularly rewarding in this respect. This study shows a practical approach using 5,6-O-isopropylidene-L-ascorbic acid (ketal of L- ascorbic acid) as a single common starting material for facile asymmetric synthesis of protected, optically pure and functionalized aldono-1,4-lactones derivatives, valuable in the synthesis of derivatives of various pharmacologically active agents for structure- v activity studies. The practicality of this new approach is demonstrated by the convenient synthesis of a series of thermal Claisen-rearranged products of 5,6-O-isopropylidene-3- O-allyl-L-ascorbic acid and 5,6-O-isopropylidene-2-O-allyl-L-ascorbic acid as the corresponding 5,6-O-isopropylidene-2-allyl-3-keto-L-galactono-γ-lactone and 5,6-O- isopropylidene-3-allyl-2-keto-L-galactono-γ-lactone respectively. The synthetic routes are economical, efficient, diastereospecific, and proceed in high yields. vi TABLE OF CONTENTS CHAPTER 1 .......................................................................................................................1 INTRODUCTION .......................................................................................................... 1 CHAPTER 2 .......................................................................................................................4 BACKGROUND AND SIGNIFICANCE...................................................................... 4 2.1 Discovery and History of L-Ascorbic Acid.......................................................... 4 2.2 Sources of L-Ascorbic Acid................................................................................ 10 2.3 Tissue Distribution of L-Ascorbic acid............................................................... 12 2.4 Biosynthesis of L-Ascorbic Acid in Animals ..................................................... 14 2.5 Biosynthesis of L-Ascorbic Acid in Plants......................................................... 18 2.6 Commercial Scale Synthesis of L-Ascorbic acid................................................ 22 2.7 Biological Functions of L-Ascorbic Acid........................................................... 26 2.7.1 L-Ascorbic Acid as an Enzyme Cofactor .................................................... 26 2.7.2 L-Ascorbic Acid in Electron Transport ....................................................... 31 2.7.3 L-Ascorbic Acid as an Antioxidant in Biological Systems ......................... 33 2.8 L-Ascorbic Acid Metabolic Enzymes................................................................. 36 2.9 Degradation and Oxidation of L-Ascorbic Acid................................................. 37 2.10 Cellular Transport and Intestinal Absorption of L-Ascorbic Acid ................... 40 2.11 Molecular Structure of L-Ascorbic Acid .......................................................... 41 2.12 Chemical and Physical Properties of L-Ascorbic Acid .................................... 45 2.13 Synthetic Derivatives and Analogues of L-Ascorbic Acid............................... 46 CHAPTER 3 ..................................................................................................................... 53 vii RESEARCH OBJECTIVE ........................................................................................... 53 CHAPTER 4 ..................................................................................................................... 55 RESULTS AND DISCUSSION................................................................................... 55 4.1 Chemo- and Regio-Selective Alkylation of L-Ascorbic Acid............................ 55 4.1.1 3-O-Alkylation of 5,6-O-Isopropylidene-L-Ascorbic Acid......................... 56 4.1.2 2-O-Alkylation of 5, 6-O-Isopropylidene-L-Ascorbic Acid........................ 59 4.1.3 2,3-O-Disubstitution of 5,6-O-Isopropylidene-L-Ascorbic Acid ................ 62 4.2 Acylation of 5, 6-O-Isopropylidene-L-Ascorbic Acid........................................ 65 4.2.1 C3-O- to C2-O Rearrangements of 3-O-Acyl-L-Ascorbic Acid Derivatives ..................................................................................................................... 67 4.3 NMR Spectroscopic Analyses of L-Ascorbic Acid and its Derivatives............. 70 4.3.1 NMR Spectroscopic Properties of 2-O- and 3-O-Substituted 5,6-O- Isopropylidene-L-Ascorbic Acid ................................................................ 71 4.4 The Sigmatropic Claisen Rearrangement of L-Ascorbic Acid Derivatives........ 75 4.4.1 The C3-O to C2 Sigmatropic Claisen Rearrangement of 5,6-O- Isopropylidene-3-O-Allylic Derivatives of L-Ascorbic Acid..................... 76 4.4.1.1 NMR Spectroscopic Analyses of Products from C3-O to C2 Sigmatropic Claisen Rearrangement of 5,6-O-Isopropylidene-3-O- Allyl-L-Ascorbic Acid Derivatives ...................................................... 77 4.4.2 The C3-O to C2 Sigmatropic Claisen Rearrangement of 5,6-O- Isopropylidene-3-O-Cinnamyl-L-Ascorbic Acid Derivatives .................... 85 viii 4.4.2.1 NMR Spectroscopic Analyses of Products from C3-O to C2 Sigmatropic Claisen Rearrangement of 5,6-O-Isopropylidene-2-O- Acetyl-3-O-Cinnamyl-L-Ascorbic Acid Derivative (10A) .................. 87 4.4.3 The C2-O to C3 Sigmatropic Claisen Rearrangement of 5,6-O- Isopropylidene-2-O-Allyl-L-Ascorbic Acid Derivatives............................ 90 4.4.3.1 NMR Spectroscopic Analyses of Products
Load more

Recommended publications
  • Dr. Soumendu Bisoi Assistant Professor Department of Chemistry, Narajole Raj College
    Dr. Soumendu Bisoi Assistant Professor Department of Chemistry, Narajole Raj College Vitamin C Vitamin C, also named as L-ascorbic acid (Asc), is a water-soluble vitamin that is essential for humans, non-human primates and a few other mammals. Vitamin C (L-ascorbic acid; Asc) is a powerful antioxidant and essential human nutrient that has extensive industrial and medicinal applications resulting in global requirements estimated at 154 thousand tons in 2007. The discovery of Asc is related with the disease of scurvy. Scurvy was a common disease in the world’s navies and sailors until the beginning of the nineteenth century, with serious symptoms such as bleeding of mucous membranes, anaemia and eventually death. In 1928, Albert Szent-Gyørgyi first isolated the Asc from adrenal glands and called it hexuronic acid. Four years later, Charles Glen King isolated Asc in his laboratory and concluded that it was the same as hexuronic acid. In 1933, Norman Haworth deduced the chemical structure of Asc (Figure 1). Figure 1 Vitamin C (L-ascorbic acid). Between 1933 and 1934, not only Haworth and fellow British chemist Edmund Hirsthad synthesised Asc, but also, independently, the Polish chemist Tadeus Reichstein, succeeded in synthesising the vitamin in bulk, making it the first vitamin to be artificially produced. The latter process made possible the cheap mass-production of semi-synthetic Asc, which was quickly marketed. Haworth was awarded the 1937 Nobel Prize in Chemistry in part for this work, but the Reichstein process, a combined chemical and bacterial fermentation sequence still used today to produce vitamin C, retained Reichstein’s name.
    [Show full text]
  • Synthesis and Characterization of New Metal-Carbon Catalysts for Hydrogenation of D-Glucose
    SYNTHESIS AND CHARACTERIZATION OF NEW METAL-CARBON CATALYSTS FOR HYDROGENATION OF D-GLUCOSE LIU JIAJIA NATIONAL UNIVERSITY OF SINGAPORE 2010 SYNTHESIS AND CHARACTERIZATION OF NEW METAL-CARBON CATALYSTS FOR HYDROGENATION OF D-GLUCOSE LIU JIAJIA (M.Eng, Tianjin University) A THESIS SUBMITTED FOR THE DEGREE OF DOCTOR OF PHILOSOPHY DEPARTMENT OF CHEMICAL AND BIOMOLECULAR ENGINEERING NATIONAL UNIVERSITY OF SINGAPORE 2010 Acknowledgement Acknowledgement I am heartily thankful to my supervisor, Assoc. Prof. Zhao X. S., George, whose constant encouragement, invaluable guidance, patience and support throughout the whole period of my PhD candidature. I would also like to thank Assoc. Prof. Zhao for his guidance on writing scientific papers including this PhD thesis. In addition, I want to express my sincerest appreciation to the Department of Chemical and Biomolecular Engineering for offering me the chance to study at NUS with a scholarship. It’s my pleasure to work with a group of brilliant, warmhearted and lovely people. Wish all my lab mates go well with their work. Particular acknowledgement goes to Dr. Liu Tao, Mr. Chia Phai Ann, Mr. Shang Zhenhua, Dr. Yuan Zeliang, Mr. Mao Ning, Mr. Liu Zhicheng, Dr. Rajarathnam D., Madam Chow Pek Jaslyn, Mdm Fam Hwee Koong Samantha, Ms Lee Chai Keng, Ms Tay Choon Yen, Mr. Toh Keng Chee, Mr. Chun See Chong, Ms. Ng Ai Mei, Ms. Lum Mei Peng Sharon, and Ms. How Yoke Leng Doris for their kind supports. I thank my parents and my husband. It is no exaggeration to say that I could not complete the PhD work without their generous help, boundless love, encouragement and support.
    [Show full text]
  • Ethoxylation of Fatty Acids
    S B N P Enzymatic Synthesis & Functional Characterization Fredrik Viklund Department of Biotechnology Stockholm Royal Institute of Technology Surfactants based on natural products — Enzymatic synthesis and functional characterization Copyright © by Fredrik Viklund ISBN --- is is the electronic version of the thesis. Compared to the printed version, it includes some minor typographical corrections. Royal Institute of Technology Printed in Stockholm AlbaNova University Center May Department of Biotechnology SE- Stockholm, Sweden Universitetsservice AB http://www.biotech.kth.se/ http://www.us-ab.se/ To Explorers Sammanfattning Tensider är molekyler som består av en vattenlöslig och en fettlöslig del. De spelar en viktig roll i produkter som rengöringsmedel, kosmetika, läkemedel och mat såväl som i många industriella processer. Tensider används i mycket stor skala vilket gör det viktigt att minska deras påverkan på miljön. Det kan åstadkommas genom att använda naturprodukter som råvaror, genom att förbättra tillverkningsmetoderna och genom att minska användningen av begränsade resurser som energi och lösningsmedel. Den här avhandlingen behandlar lipaskatalyserad syntes av naturprodukts- baserade tensider. Den omfattar också studier av de framställda tensiderna; dels som antioxidanter i oljor, dels som tensider för att öka lösligheten av läkemedel. Omättade fettsyraestrar av askorbinsyra framställdes genom katalys med Candida antarctica lipas B i t-amylalkohol och i joniska vätskor. Höga utbyten av askorbyloleat erhölls i en jonisk vätska som formgivits för att öka lösligheten av fettsyran, när reaktionen kördes under vakuum. Vi fann att askorbyloleat är amorft och att det är en bättre antioxidant än askorbylpalmitat i rapsolja. Polyetylenglykol (PEG)-stearat, PEG -hydroxystearat och en rad PEG -acyloxy-stearater framställdes i en vakuumdriven och lösningsmedels- fri uppställning med lipas B från C.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 6,610,863 B2 Arumugam Et Al
    USOO6610863B2 (12) United States Patent (10) Patent No.: US 6,610,863 B2 Arumugam et al. (45) Date of Patent: Aug. 26, 2003 (54) CONTINUOUS PROCESS FOR PRODUCING DE 199 04 821 C1, 7/2000 L-ASCORBIC ACID EP O554090 A2 4/1983 EP 1 048 663 A1 11/2000 (75) Inventors: Bhaskar Krishna Arumugam, SE 1. is : 3.3. Kingsport, TN (US); Nick Allen GB 2O34 315 * 6/1980 Collins, Fall Branch, TN (US); JP 73015931 5/1973 Transito Lynne Macias, Petal, MS WO WO 87/0O839 2/1987 (US); Steven Thomas Perri, Kingsport, WO WO 97/13761 4/1997 TN (US); Jeffrey Earl Grant Powell, WO WO 99/07691 2/1999 Blountville, TN (US); Chester Wayne WO WOOO46216 8/2000 Sink, Kingsport, TN (US); Michael Roy Cushman, Punta Gorda, FL (US) OTHER PUBLICATIONS Anderson, S. et al., Production of 2-Keto-L-Gulonate, an (73) Assignee: Eastman Chemical Company, Intermediate in L-AScorbate Synthesis, by a Genetically Kingsport, TN (US) Modified Erwinia herbicola, Science, 230, pp. 144-149, 1985. (*) Notice: Subject to any disclaimer, the term of this Regna, P.P. et al., Kinetics of Transformation of 2-Keto patent is extended or adjusted under 35 polyhydroxy Acids, J. Am. Chem. Soc., 66, pp. 246-250, U.S.C. 154(b) by 0 days. 1944. Reichstein, T. et al., Eine ergiebige Synthese der 1-AScorb (21) Appl. No.: 10/037,126 ins?ure (C-Vitamine)) Helv. Chim. Acta, 17, pp. 311-328, 1934 * See Information Disclosure Statement for Descrip (22) Filed: Dec. 21, 2001 tion. (65) Prior Publication Data Saito, Y., Direct Fermentation of 2-Keto-L-Gulonic Acid in Recombinant Gluconobacter Oxydans, Biotechnol.
    [Show full text]
  • Chemistry: Human Activity, Chemical Reactivity
    Chemistry: Human Activity, Chemical chapters. For example, the chapter on carbon com- Reactivity pounds starts with a case study of methane clathrates, Peter Mahaffy, Roy Tasker, Bob Bucat, John C. and that on chemical reactions and energy, with a Kotz, Gabriela C. Weaver, Paul M. Treichel, John E. case study of hydrogen as a fuel. The more obviously McMurry organic chapters use contexts from pharmaceuticals Nelson Education Ltd., 2010 or biological chemistry, with case studies on curing ISBN-13: 978-0-17660-625-1 and death and dying in the aromatics compounds ISBN-10: 0176606254 chapter, and a case study on the discovery of penicillin in the carbonyl compound chapter. These case studies are fascinating and a useful resource in themselves, reviewed by Tina L. Overton and I looked forward to each one. It is perhaps a little unfortunate that the first two are about drug abuse, There are many general chemistry textbooks on the and that some potential adopters may be prudish market and they all almost inevitably cover similar enough to be put off by that. But in each case the content. Academic staff choose these books for topics are discussed in their scientific context, and in their undergraduate students based on many crite- a way that helps us to appreciate (in these cases) the ria; level, detailed content, layout, design, chapter power of analytical techniques. order, habit, etc. Chemistry: Human Activity, Chemical The case studies are not the only place that Reactivity may give academics additional criteria the essential importance of chemistry is discussed. to consider. The book is authored by a well-known Real-life context is embedded within the text, often team of chemical educators who in a way that encourages stu- have a particular passion for rep- dents to think about how we know resenting chemistry visually, using what we know, and that demon- electronic resources to enhance strates the scientific method effec- conceptual understanding, and for tively.
    [Show full text]
  • Homology Modeling and Structural Analysis of Theflavanone 3- Hydroxylase (F3H) and Flavonoid 3`Hydroxylase (F3`H) Genes from Ginkgo Biloba (L.)
    IOSR Journal of Biotechnology and Biochemistry (IOSR-JBB) ISSN: 2455-264X, Volume 7, Issue 1 (Jan. – Feb. 2021), PP 01-21 www.iosrjournals.org Homology Modeling and Structural Analysis of theFlavanone 3- Hydroxylase (F3H) and Flavonoid 3`hydroxylase (F3`H) Genes from Ginkgo biloba (L.) Mohamed ZoelfakarSayedAhmed* (Genetic Resources Department, Desert Research Center (DRC), 1, Mathaf El-MatariyaStreet, El-Matariya B.O.P 11753 El-Matariya, Cairo, Egypt.) *corresponding author: (Ahmed, M.Z.S.) Abstract: Ginkgo biloba L. is a well-known living gymnosperm fossil that has medicinal, biologically and economically value in the worldwide. In this study, bioinformatics analysis based on Homology modeling were obtainedsuch as flavanone 3-hydroxylase (GbF3H) and flavonoid 3`-hydroxylase (GbF3`H) from Ginkgo biloba L. are key enzymes in involved pathway of plant flavonoids and the anthocyanin.The full-length cDNA of F3H gene sequence (GbF3H) was isolated from G. bilobacontained a 1074 bp open reading frame(ORF) encoding a 357- amino-acid protein. The deduced GbF3H protein showed high identities to other plant F3Hs.For the full-length cDNA GbF3`H gene was contained a1674 bpopen reading frame (ORF)encoding a 556 amino acid protein.As well as, Multiple Sequence Alignment (MSAs) of selected of 30 amino acid were done using MEGA7 software with high identify and similarity.Phylogenetic analysis was performed using the amino acid sequence of GbF3H and GbF3′H with other known plant-specific F3Hs and F3′Hs to each Gymnosperm (Naked seed) and Angiosperms (Flower plant).The parameters computed by ProtParam software was obtained to the molecular weight and grand average of hydropathicity (GRAVY) for GbF3H and GbF3`H protein.The parameters computed by Protscale software was obtained to hydrophilicity scales based on different chemical and physical properties of the amino acids.We have investigated homology modelling and structure analysis to characterize of two genes (GbF3H and GbF3`H) from Ginkgo biloba to identity percentage using the SWISS-MODEL template library (SMTL).
    [Show full text]
  • Nutritional Biochemistry of the Vitamins, Second Edition David A
    Cambridge University Press 0521803888 - Nutritional Biochemistry of the Vitamins, Second Edition David A. Bender Index More information Index abetalipoproteinemia, 36, 125 adenosylhomocysteine, 290f absorption, 9 adequacy, criteria, 10–2 biotin, 325, 329 adequate intake (see also reference intakes), 21, calcium, 93 23 carotene, 35, 40–1, 42 adipic acid oxidation, 191–2 folate, 273–4 adipocytes, vitamin D, 97 iron, 369 adipose tissue, carotene, 72 niacin, 203 retinol, 37 pantothenic acid, 346 vitamin D, 106 phosphate, 93 cADP-ribose, 219–21 riboflavin, 175–6 ADP-ribose cyclase, 219, 220f thiamin, 150–1 ADP-ribosyltransferase, 204f, 206, 215–7 vitamin A, 35–6 adrenal gland, lycopene, 71 vitamin B6, 234 adriamycin, 194, 195f vitamin B12, 300–1, 314 advanced glycation endproducts, 264 vitamin C, 361 aglycone, 402 vitaminD,83 agmatine, 240t vitamin E, 113 AI (adequate intake, see also reference intakes), vitamin K, 133–4 21, 23 accessory food factors, 1 β-alanine, 266 Accutane®,72 alanine, transamination, 242t acetomenaphthone, 132f alanine-glyoxylate transaminase, 20t acetyl choline, 165, 221, 390f alcohol, 62, 151 acetyl CoA carboxylase, 330, 333t dehydrogenase, vitamin A, 38 acetylator status, 355 aldehyde dehydrogenase, 235 N-acetylglutamate, 306 aldehyde oxidase, 41f, 188, 207 activation coefficient, glutathione reductase, alfacalcidiol, 107 197 alkaline phosphatase, 96, 103, 104t, 235 transaminases, 251–2 allicin, 402f transketolase, 168–9 alliin, 402f acute phase proteins, 64 allinase, 401 acyl carnitine excretion, 306 allithiamin, 149f, 150 acyl carrier protein, 350 alloxan, 219, 229–30 acyl CoA dehydrogenase, 185, 191–2 all-R-tocopherol, 112 acyl CoA:retinol acyltransferase, 36 allyl sulfur compounds, 401–2 acylation, proteins 352 alopecia, 97, 101, 337 S-adenosyl methionine, 284, 289, 290f Alzheimer’s disease, 130, 169–70, 346, 356 decarboxylase, 267 amadorins, 264 463 © Cambridge University Press www.cambridge.org Cambridge University Press 0521803888 - Nutritional Biochemistry of the Vitamins, Second Edition David A.
    [Show full text]
  • Recent Patents on Vitamin C: Opportunities for Crop Improvement and Single-Step Biological Manufacture Robert D
    Recent Patents on Food, Nutrition & Agriculture, 2009, 1, 39-49 39 Recent Patents on Vitamin C: Opportunities for Crop Improvement and Single-Step Biological Manufacture Robert D. Hancock* Plant Products and Food Quality, Scottish Crop Research Institute, Invergowrie, Dundee DD2 5DA. United Kingdom Received: August 1, 2008; Accepted: September 9, 2008; Revised: September 9, 2008 Abstract: Vitamin C is an essential human nutrient obtained primarily from plant foods. Despite the necessity of the vitamin for human health and the essential role that it plays in plant stress resistance, it is only in the last decade that an understanding of its biosynthesis in plants has emerged. These fundamental discoveries present for the first time the opportunity to manipulate crop plants for improved human nutrition and enhanced agronomic performance and are discussed in relation to recent patents protecting aspects of vitamin C synthesis and degradation in plants. Vitamin C has a wide range of medicinal and industrial uses resulting in an annual market exceeding US$600 million. In recent years, there has been strong competition in vitamin C markets as a result of emerging Chinese producers and one response has been increased investment in research and development for the biological manufacture of the vitamin. Knowledge of the plant biosynthetic pathway has provided novel opportunities for the synthesis of vitamin C in yeasts, although successes have been limited to date. A more promising route is the direct synthesis of vitamin C in acetic acid bacteria and significant research and development has gone into the genetic improvement of appropriate strains. Keywords: Ascorbic acid, fermentation, Reichstein process, Gluconobacter, sorbitol, sorbosone dehydrogenase.
    [Show full text]
  • Ascorbic Acid Handling/Processing
    United States Department of Agriculture Agricultural Marketing Service | National Organic Program Document Cover Sheet https://www.ams.usda.gov/rules-regulations/organic/national-list/petitioned Document Type: ☐ National List Petition or Petition Update A petition is a request to amend the USDA National Organic Program’s National List of Allowed and Prohibited Substances (National List). Any person may submit a petition to have a substance evaluated by the National Organic Standards Board (7 CFR 205.607(a)). Guidelines for submitting a petition are available in the NOP Handbook as NOP 3011, National List Petition Guidelines. Petitions are posted for the public on the NOP website for Petitioned Substances. ☒ Technical Report A technical report is developed in response to a petition to amend the National List. Reports are also developed to assist in the review of substances that are already on the National List. Technical reports are completed by third-party contractors and are available to the public on the NOP website for Petitioned Substances. Contractor names and dates completed are available in the report. Ascorbic Acid Handling/Processing 1 Identification of Petitioned Substance 18 2 Chemical Names: 19 Trade Names: 3 Ascorbic Acid Magnorbin 4 L-Ascorbic Acid Ascorbicap 5 (2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy- Hybrin 6 2H-furan-5-one Cescorbat 7 L-Threoascorbic Acid 8 CAS Numbers: 9 Other Names: 50-81-7 10 Vitamin C 11 Cevitamic Acid Other Codes: 12 Xyloascorbic Acid, L EC No. 200-066-2 13 Vitacimin ICSC No. 0379 14 Vitacin FEMA No. 2109 15 Ascoltin RTECS No.
    [Show full text]
  • Discovery of Industrially Relevant Oxidoreductases
    DISCOVERY OF INDUSTRIALLY RELEVANT OXIDOREDUCTASES Thesis Submitted for the Degree of Master of Science by Kezia Rajan, B.Sc. Supervised by Dr. Ciaran Fagan School of Biotechnology Dublin City University Ireland Dr. Andrew Dowd MBio Monaghan Ireland January 2020 Declaration I hereby certify that this material, which I now submit for assessment on the programme of study leading to the award of Master of Science, is entirely my own work, and that I have exercised reasonable care to ensure that the work is original, and does not to the best of my knowledge breach any law of copyright, and has not been taken from the work of others save and to the extent that such work has been cited and acknowledged within the text of my work. Signed: ID No.: 17212904 Kezia Rajan Date: 03rd January 2020 Acknowledgements I would like to thank the following: God, for sending me angels in the form of wonderful human beings over the last two years to help me with any- and everything related to my project. Dr. Ciaran Fagan and Dr. Andrew Dowd, for guiding me and always going out of their way to help me. Thank you for your patience, your advice, and thank you for constantly believing in me. I feel extremely privileged to have gotten an opportunity to work alongside both of you. Everything I’ve learnt and the passion for research that this project has sparked in me, I owe it all to you both. Although I know that words will never be enough to express my gratitude, I still want to say a huge thank you from the bottom of my heart.
    [Show full text]
  • The Roots—A Short History of Industrial Microbiology and Biotechnology
    Appl Microbiol Biotechnol (2013) 97:3747–3762 DOI 10.1007/s00253-013-4768-2 MINI-REVIEW The roots—a short history of industrial microbiology and biotechnology Klaus Buchholz & John Collins Received: 20 December 2012 /Revised: 8 February 2013 /Accepted: 9 February 2013 /Published online: 17 March 2013 # Springer-Verlag Berlin Heidelberg 2013 Abstract Early biotechnology (BT) had its roots in fasci- mainly secondary metabolites, e.g. steroids obtained by nating discoveries, such as yeast as living matter being biotransformation. By the mid-twentieth century, biotech- responsible for the fermentation of beer and wine. Serious nology was becoming an accepted specialty with courses controversies arose between vitalists and chemists, resulting being established in the life sciences departments of several in the reversal of theories and paradigms, but prompting universities. Starting in the 1970s and 1980s, BT gained the continuing research and progress. Pasteur’s work led to the attention of governmental agencies in Germany, the UK, establishment of the science of microbiology by developing Japan, the USA, and others as a field of innovative potential pure monoculture in sterile medium, and together with the and economic growth, leading to expansion of the field. work of Robert Koch to the recognition that a single path- Basic research in Biochemistry and Molecular Biology dra- ogenic organism is the causative agent for a particular matically widened the field of life sciences and at the same disease. Pasteur also achieved innovations for industrial time unified them considerably by the study of genes and processes of high economic relevance, including beer, wine their relatedness throughout the evolutionary process.
    [Show full text]
  • Unity in Diversity, a Systems Approach to Regulating Plant Cell Physiology by 2-Oxoglutarate-Dependent Dioxygenases
    ORIGINAL RESEARCH ARTICLE published: 11 March 2015 doi: 10.3389/fpls.2015.00098 Unity in diversity, a systems approach to regulating plant cell physiology by 2-oxoglutarate-dependent dioxygenases Siddhartha Kundu*† School of Computational and Integrative Sciences, Jawaharlal Nehru University, New Delhi, India Edited by: Could a disjoint group of enzymes synchronize their activities and execute a complex Stefan Martens, Edmund Mach multi-step, measurable, and reproducible response? Here, I surmise that the Foundation, Italy alpha-ketoglutarate dependent superfamily of non-haem iron (II) dioxygenases could Reviewed by: influence cell physiology as a cohesive unit, and that the broad spectra of substrates Qing Liu, Commonwealth Scientific and Industrial Research transformed is an absolute necessity to this portrayal. This eclectic group comprises Organisation, Australia members from all major taxa, and participates in pesticide breakdown, hypoxia signaling, Vinay Kumar, National Institute of and osmotic stress neutralization. The oxidative decarboxylation of 2-oxoglutarate to Plant Genome Research, India succinate is coupled with a concomitant substrate hydroxylation and, in most cases, is *Correspondence: followed by an additional specialized conversion. The domain profile of a protein sequence Siddhartha Kundu, School of Computational and Integrative was used as an index of miscellaneous reaction chemistry and interpreted alongside Sciences, Jawaharlal Nehru existent kinetic data in a linear model of integrated function. Statistical parameters University, New Mehrauli Road, were inferred by the creation of a novel, empirically motivated flat-file database of New Delhi, Delhi 110067, India over 3800 sequences (DB2OG) with putative 2-oxoglutarate dependent activity. The e-mail: siddhartha_kundu@ yahoo.co.in; collated information was categorized on the basis of existing annotation schema.
    [Show full text]