Literature DB >> 18759479

Synthesis of uridine 5'-diphosphoiduronic acid: a potential substrate for the chemoenzymatic synthesis of heparin.

Michel Weïwer1, Trevor Sherwood, Dixy E Green, Miao Chen, Paul L DeAngelis, Jian Liu, Robert J Linhardt.   

Abstract

An improved understanding of the biological activities of heparin requires structurally defined heparin oligosaccharides. The chemoenzymatic synthesis of heparin oligosaccharides relies on glycosyltransferases that use UDP-sugar nucleotides as donors. Uridine 5'-diphosphoiduronic acid (UDP-IdoA) and uridine 5'-diphosphohexenuronic acid (UDP-HexUA) have been synthesized as potential analogues of uridine 5'-diphosphoglucuronic acid (UDP-GlcA) for enzymatic incorporation into heparin oligosaccharides. Non-natural UDP-IdoA and UDP-HexUA were tested as substrates for various glucuronosyltransferases to better understand enzyme specificity.

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Year:  2008        PMID： 18759479      PMCID： PMC2639712          DOI： 10.1021/jo801409c

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  24 in total

1.  Syntheses of unnatural N-substituted UDP-galactosamines as alternative substrates for N-acetylgalactosaminyl transferases.

Authors:  Daniel Lazarevic; Joachim Thiem
Journal:  Carbohydr Res       Date:  2002-11-19       Impact factor: 2.104

2.  UDP-N-trifluoroacetylglucosamine as an alternative substrate in N-acetylglucosaminyltransferase reactions.

Authors:  R F Sala; S L MacKinnon; M M Palcic; M E Tanner
Journal:  Carbohydr Res       Date:  1998-01       Impact factor: 2.104

3.  Determination of the substrate specificities of N-acetyl-d-glucosaminyltransferase.

Authors:  Miao Chen; Arlene Bridges; Jian Liu
Journal:  Biochemistry       Date:  2006-10-10       Impact factor: 3.162

4.  Enzymatic redesigning of biologically active heparan sulfate.

Authors:  Jinghua Chen; Fikri Y Avci; Eva M Muñoz; Lynda M McDowell; Miao Chen; Lars C Pedersen; Lijuan Zhang; Robert J Linhardt; Jian Liu
Journal:  J Biol Chem       Date:  2005-10-31       Impact factor: 5.157

5.  Enzymatic synthesis of heparin related polysaccharides on sensor chips: rapid screening of heparin-protein interactions.

Authors:  Eva Muñoz; Ding Xu; Fikri Avci; Melissa Kemp; Jian Liu; Robert J Linhardt
Journal:  Biochem Biophys Res Commun       Date:  2005-11-17       Impact factor: 3.575

6.  Synthesis of heparin-like oligosaccharides on polymer supports.

Authors:  Rafael Ojeda; Olimpia Terentí; José-Luis de Paz; Manuel Martín-Lomas
Journal:  Glycoconj J       Date:  2004       Impact factor: 2.916

7.  Biosynthesis of heparin. Use of Escherichia coli K5 capsular polysaccharide as a model substrate in enzymic polymer-modification reactions.

Authors:  M Kusche; H H Hannesson; U Lindahl
Journal:  Biochem J       Date:  1991-04-01       Impact factor: 3.857

8.  Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides.

Authors:  Heather C Losey; Jiqing Jiang; John B Biggins; Markus Oberthür; Xiang Yang Ye; Steven D Dong; Daniel Kahne; Jon S Thorson; Christopher T Walsh
Journal:  Chem Biol       Date:  2002-12

9.  Enzymatic synthesis of antithrombin III-binding heparan sulfate pentasaccharide.

Authors:  Balagurunathan Kuberan; Miroslaw Z Lech; David L Beeler; Zhengliang L Wu; Robert D Rosenberg
Journal:  Nat Biotechnol       Date:  2003-10-05       Impact factor: 54.908

10.  Biosynthesis of 3-O-sulfated heparan sulfate: unique substrate specificity of heparan sulfate 3-O-sulfotransferase isoform 5.

Authors:  Jinghua Chen; Michael B Duncan; Kevin Carrick; R Marshall Pope; Jian Liu
Journal:  Glycobiology       Date:  2003-08-07       Impact factor: 4.313
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  5 in total

1.  Comamonas testosteronan synthase, a bifunctional glycosyltransferase that produces a unique heparosan polysaccharide analog.

Authors:  Nigel J Otto; Kemal Solakyildirim; Robert J Linhardt; Paul L DeAngelis
Journal:  Glycobiology       Date:  2011-05-24       Impact factor: 4.313

2.  Improved one-pot multienzyme (OPME) systems for synthesizing UDP-uronic acids and glucuronides.

Authors:  Musleh M Muthana; Jingyao Qu; Mengyang Xue; Timofey Klyuchnik; Alex Siu; Yanhong Li; Lei Zhang; Hai Yu; Lei Li; Peng G Wang; Xi Chen
Journal:  Chem Commun (Camb)       Date:  2015-03-18       Impact factor: 6.222

3.  A simple strategy for glycosyltransferase-catalyzed aminosugar nucleotide synthesis.

Authors:  Jianjun Zhang; Shanteri Singh; Ryan R Hughes; Maoquan Zhou; Manjula Sunkara; Andrew J Morris; Jon S Thorson
Journal:  Chembiochem       Date:  2014-03-21       Impact factor: 3.164

Review 4.  Chemoenzymatic synthesis of glycosaminoglycans: re-creating, re-modeling and re-designing nature's longest or most complex carbohydrate chains.

Authors:  Paul L DeAngelis; Jian Liu; Robert J Linhardt
Journal:  Glycobiology       Date:  2013-03-11       Impact factor: 4.313

Review 5.  Chemoenzymatic synthesis of heparan sulfate and heparin.

Authors:  Jian Liu; Robert J Linhardt
Journal:  Nat Prod Rep       Date:  2014-09-08       Impact factor: 13.423
  5 in total

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