Literature DB >> 29512241

Controlled Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides.

Weigang Lu1, Chengli Zong1,2, Pradeep Chopra1, Lauren E Pepi2, Yongmei Xu3, I Jonathan Amster2, Jian Liu3, Geert-Jan Boons1,2,4.   

Abstract

A chemoenzymatic approach has been developed for the preparation of diverse libraries of heparan sulfate (HS) oligosaccharides. It employs chemically synthesized oligosaccharides having a chemical entity at a GlcN residue, which in unanticipated manners influences the site of modification by NST, C5-Epi/2-OST and 6-OST1 /6-OST3 , thus resulting in oligosaccharides differing in N/O-sulfation and epimerization pattern. The enzymatic transformations defined fine substrate requirements of NST, C5-Epi, 2-OST, and 6-OST.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  enzymes; epimers; heparan; oligosaccharides; synthetic methods

Mesh：

Substances：

Year:  2018        PMID： 29512241      PMCID： PMC5996245          DOI： 10.1002/anie.201800387

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  29 in total

1.  Single-entity heparan sulfate glycomimetic clusters for therapeutic applications.

Authors:  Peter C Tyler; Scott E Guimond; Jeremy E Turnbull; Olga V Zubkova
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-13       Impact factor: 15.336

2.  Homogeneous low-molecular-weight heparins with reversible anticoagulant activity.

Authors:  Yongmei Xu; Chao Cai; Kasemsiri Chandarajoti; Po-Hung Hsieh; Lingyun Li; Truong Q Pham; Erica M Sparkenbaugh; Juzheng Sheng; Nigel S Key; Rafal Pawlinski; Edward N Harris; Robert J Linhardt; Jian Liu
Journal:  Nat Chem Biol       Date:  2014-02-23       Impact factor: 15.040

3.  Heparan Sulfate Microarray Reveals That Heparan Sulfate-Protein Binding Exhibits Different Ligand Requirements.

Authors:  Chengli Zong; Andre Venot; Xiuru Li; Weigang Lu; Wenyuan Xiao; Jo-Setti L Wilkes; Catherina L Salanga; Tracy M Handel; Lianchun Wang; Margreet A Wolfert; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

4.  A novel role for 3-O-sulfated heparan sulfate in herpes simplex virus 1 entry.

Authors:  D Shukla; J Liu; P Blaiklock; N W Shworak; X Bai; J D Esko; G H Cohen; R J Eisenberg; R D Rosenberg; P G Spear
Journal:  Cell       Date:  1999-10-01       Impact factor: 41.582

5.  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

Review 6.  A synthetic antithrombin III binding pentasaccharide is now a drug! What comes next?

Authors:  Maurice Petitou; Constant A A van Boeckel
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-14       Impact factor: 15.336

7.  Integrated Approach to Identify Heparan Sulfate Ligand Requirements of Robo1.

Authors:  Chengli Zong; Rongrong Huang; Eduard Condac; Yulun Chiu; Wenyuan Xiao; Xiuru Li; Weigang Lu; Mayumi Ishihara; Shuo Wang; Annapoorani Ramiah; Morgan Stickney; Parastoo Azadi; I Jonathan Amster; Kelley W Moremen; Lianchun Wang; Joshua S Sharp; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2016-09-27       Impact factor: 15.419

8.  Redirecting the substrate specificity of heparan sulfate 2-O-sulfotransferase by structurally guided mutagenesis.

Authors:  Heather N Bethea; Ding Xu; Jian Liu; Lars C Pedersen
Journal:  Proc Natl Acad Sci U S A       Date:  2008-11-20       Impact factor: 11.205

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.  Tetrasaccharide iteration synthesis of a heparin-like dodecasaccharide and radiolabelling for in vivo tissue distribution studies.

Authors:  Steen U Hansen; Gavin J Miller; Claire Cole; Graham Rushton; Egle Avizienyte; Gordon C Jayson; John M Gardiner
Journal:  Nat Commun       Date:  2013       Impact factor: 14.919
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  8 in total

Review 1.  Oligosaccharide Synthesis and Translational Innovation.

Authors:  Larissa Krasnova; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2019-02-18       Impact factor: 15.419

Review 2.  Harnessing glycoenzyme engineering for synthesis of bioactive oligosaccharides.

Authors:  Mounir Benkoulouche; Régis Fauré; Magali Remaud-Siméon; Claire Moulis; Isabelle André
Journal:  Interface Focus       Date:  2019-02-15       Impact factor: 3.906

3.  Perspective on computational simulations of glycosaminoglycans.

Authors:  Balaji Nagarajan; Nehru Viji Sankaranarayanan; Umesh R Desai
Journal:  Wiley Interdiscip Rev Comput Mol Sci       Date:  2018-09-10

Review 4.  Mass Spectrometry-Based Techniques to Elucidate the Sugar Code.

Authors:  Márkó Grabarics; Maike Lettow; Carla Kirschbaum; Kim Greis; Christian Manz; Kevin Pagel
Journal:  Chem Rev       Date:  2021-09-07       Impact factor: 72.087

Review 5.  Recent progress in synthesis of carbohydrates with sugar nucleotide-dependent glycosyltransferases.

Authors:  Lan Na; Riyao Li; Xi Chen
Journal:  Curr Opin Chem Biol       Date:  2020-12-10       Impact factor: 8.822

6.  Selective Binding of Heparin/Heparan Sulfate Oligosaccharides to Factor H and Factor H-Related Proteins: Therapeutic Potential for C3 Glomerulopathies.

Authors:  Markus A Loeven; Marissa L Maciej-Hulme; Cansu Yanginlar; Melanie C Hubers; Edwin Kellenbach; Mark de Graaf; Toin H van Kuppevelt; Jack Wetzels; Ton J Rabelink; Richard J H Smith; Johan van der Vlag
Journal:  Front Immunol       Date:  2021-08-18       Impact factor: 7.561

7.  Analytical challenges of glycosaminoglycans at biological interfaces.

Authors:  Gergo Peter Szekeres; Kevin Pagel; Zsuzsanna Heiner
Journal:  Anal Bioanal Chem       Date:  2021-10-14       Impact factor: 4.142

8.  Chemical synthesis of human syndecan-4 glycopeptide bearing O-, N-sulfation and multiple aspartic acids for probing impacts of the glycan chain and the core peptide on biological functions.

Authors:  Weizhun Yang; Yigitcan Eken; Jicheng Zhang; Logan Emerson Cole; Sherif Ramadan; Yongmei Xu; Zeren Zhang; Jian Liu; Angela K Wilson; Xuefei Huang
Journal:  Chem Sci       Date:  2020-05-11       Impact factor: 9.825
  8 in total

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