Literature DB >> 25858766

Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide.

Baolin Wu1, Na Wei, Vireak Thon, Mohui Wei, Zaikuan Yu, Yongmei Xu, Xi Chen, Jian Liu, Peng George Wang, Tiehai Li.   

Abstract

A biotinylated heparosan hexasaccharide was synthesized using a one-pot multi-enzyme strategy, in situ activation and transfer of N-trifluoroacetylglucosamine (GlcNTFA) to a heparin backbone significantly improved the synthetic efficiency. The biotinylated hexasaccharide could serve as a flexible core to diversify its conversion into heparan sulfate isoforms with potential biological applications and therapeutics.

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Year:  2015        PMID： 25858766      PMCID： PMC4472006          DOI： 10.1039/c5ob00462d

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  52 in total

Review 1.  Order out of chaos: assembly of ligand binding sites in heparan sulfate.

Authors:  Jeffrey D Esko; Scott B Selleck
Journal:  Annu Rev Biochem       Date:  2001-11-09       Impact factor: 23.643

2.  Identification of a distinct, cryptic heparosan synthase from Pasteurella multocida types A, D, and F.

Authors:  Paul L Deangelis; Carissa L White
Journal:  J Bacteriol       Date:  2004-12       Impact factor: 3.490

3.  Development of a recombinant antithrombin variant as a potent antidote to fondaparinux and other heparin derivatives.

Authors:  Elsa P Bianchini; Judicael Fazavana; Veronique Picard; Delphine Borgel
Journal:  Blood       Date:  2010-11-03       Impact factor: 22.113

4.  Conformational locking of the glycosyl acceptor for stereocontrol in the key step in the synthesis of heparin.

Authors:  Hernan A Orgueira; Alessandra Bartolozzi; Peter Schell; Peter H Seeberger
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-17       Impact factor: 15.336

Review 5.  Bleeding risk and reversal strategies for old and new anticoagulants and antiplatelet agents.

Authors:  M Levi; E Eerenberg; P W Kamphuisen
Journal:  J Thromb Haemost       Date:  2011-09       Impact factor: 5.824

6.  N-benzyl-2,3-oxazolidinone as a glycosyl donor for selective alpha-glycosylation and one-pot oligosaccharide synthesis involving 1,2-cis-glycosylation.

Authors:  Shino Manabe; Kazuyuki Ishii; Yukishige Ito
Journal:  J Am Chem Soc       Date:  2006-08-23       Impact factor: 15.419

7.  Identification that KfiA, a protein essential for the biosynthesis of the Escherichia coli K5 capsular polysaccharide, is an alpha -UDP-GlcNAc glycosyltransferase. The formation of a membrane-associated K5 biosynthetic complex requires KfiA, KfiB, and KfiC.

Authors:  N Hodson; G Griffiths; N Cook; M Pourhossein; E Gottfridson; T Lind; K Lidholt; I S Roberts
Journal:  J Biol Chem       Date:  2000-09-01       Impact factor: 5.157

Review 8.  Fondaparinux: a synthetic heparin pentasaccharide as a new antithrombotic agent.

Authors:  Jeanine M Walenga; Walter P Jeske; M Michel Samama; F Xavier Frapaise; Rodger L Bick; Jawed Fareed
Journal:  Expert Opin Investig Drugs       Date:  2002-03       Impact factor: 6.206

Review 9.  Glycan microarrays for decoding the glycome.

Authors:  Cory D Rillahan; James C Paulson
Journal:  Annu Rev Biochem       Date:  2011       Impact factor: 23.643

10.  Modular synthesis of heparan sulfate oligosaccharides for structure-activity relationship studies.

Authors:  Sailaja Arungundram; Kanar Al-Mafraji; Jinkeng Asong; Franklin E Leach; I Jonathan Amster; Andre Venot; Jeremy E Turnbull; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419
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  4 in total

Review 1.  Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly.

Authors:  Nitin J Pawar; Lei Wang; Takuya Higo; Chandrabali Bhattacharya; Pavan K Kancharla; Fuming Zhang; Kedar Baryal; Chang-Xin Huo; Jian Liu; Robert J Linhardt; Xuefei Huang; Linda C Hsieh-Wilson
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-06       Impact factor: 15.336

2.  3-O sulfation of heparin leads to hepatotropism and longer circulatory half-life.

Authors:  Colton M Miller; Yongmei Xu; Katrina M Kudrna; Blake E Hass; Brianna M Kellar; Andrew W Egger; Jian Liu; Edward N Harris
Journal:  Thromb Res       Date:  2018-05-17       Impact factor: 3.944

3.  Chemoenzymatic synthesis of unmodified heparin oligosaccharides: cleavage of p-nitrophenyl glucuronide by alkaline and Smith degradation.

Authors:  Xing Zhang; Yongmei Xu; Po-Hung Hsieh; Jian Liu; Lei Lin; Eric P Schmidt; Robert J Linhardt
Journal:  Org Biomol Chem       Date:  2017-02-01       Impact factor: 3.876

4.  Engineer P. multocida Heparosan Synthase 2 (PmHS2) for Size-Controlled Synthesis of Longer Heparosan Oligosaccharides.

Authors:  Lan Na; Hai Yu; John B McArthur; Tamashree Ghosh; Thomas Asbell; Xi Chen
Journal:  ACS Catal       Date:  2020-05-11       Impact factor: 13.084
  4 in total

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