Literature DB >> 23293947

Fluorous supported modular synthesis of heparan sulfate oligosaccharides.

Chengli Zong1, Andre Venot, Omkar Dhamale, Geert-Jan Boons.   

Abstract

The modular synthesis of heparan sulfate fragments is greatly facilitated by employing an anomeric aminopentyl linker protected by a benzyloxycarbonyl group modified by a perfluorodecyl tag, which made it possible to purify highly polar intermediates by fluorous solid phase extraction. This tagging methodology made it also possible to perform repeated glycosylations to drive reactions to completion.

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Year:  2013        PMID： 23293947      PMCID： PMC3563243          DOI： 10.1021/ol303270v

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  30 in total

1.  Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers.

Authors:  Firoz A Jaipuri; Nicola L Pohl
Journal:  Org Biomol Chem       Date:  2008-05-16       Impact factor: 3.876

Review 2.  The molecular basis and functional implications of chemokine interactions with heparan sulphate.

Authors:  Hugues Lortat-Jacob
Journal:  Curr Opin Struct Biol       Date:  2009-09-30       Impact factor: 6.809

3.  Dimethylformamide: an unusual glycosylation modulator.

Authors:  Shao-Ru Lu; Yen-Hsun Lai; Jiun-Han Chen; Chih-Yueh Liu; Kwok-Kong Tony Mong
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-17       Impact factor: 15.336

4.  A synthetic heparan sulfate oligosaccharide library reveals the novel enzymatic action of D-glucosaminyl 3-O-sulfotransferase-3a.

Authors:  Thao Kim Nu Nguyen; Sailaja Arungundram; Vy My Tran; Karthik Raman; Kanar Al-Mafraji; Andre Venot; Geert-Jan Boons; Balagurunathan Kuberan
Journal:  Mol Biosyst       Date:  2011-11-24

5.  Heparan sulfate glycomics: towards systems biology strategies.

Authors:  Jeremy E Turnbull
Journal:  Biochem Soc Trans       Date:  2010-10       Impact factor: 5.407

6.  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

7.  Oligosaccharide synthesis in microreactors.

Authors:  Frédéric R Carrel; Karolin Geyer; Jeroen D C Codée; Peter H Seeberger
Journal:  Org Lett       Date:  2007-05-10       Impact factor: 6.005

8.  Synthesis and applications of a light-fluorous glycosyl donor.

Authors:  Fa Zhang; Wei Zhang; Yan Zhang; Dennis P Curran; Gang Liu
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

9.  Convergent stereoselective synthesis of multiple sulfated GlcNα(1,4)GlcAβ(1,4) dodecasaccharides.

Authors:  Hiroshi Tanaka; Yusuke Tateno; Takashi Takahashi
Journal:  Org Biomol Chem       Date:  2012-11-07       Impact factor: 3.876

Review 10.  Interactions between heparan sulfate and proteins: the concept of specificity.

Authors:  Johan Kreuger; Dorothe Spillmann; Jin-ping Li; Ulf Lindahl
Journal:  J Cell Biol       Date:  2006-07-31       Impact factor: 10.539
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  19 in total

Review 1.  Synthetic Oligosaccharide Libraries and Microarray Technology: A Powerful Combination for the Success of Current Glycosaminoglycan Interactomics.

Authors:  Vitor H Pomin; Xu Wang
Journal:  ChemMedChem       Date:  2017-12-06       Impact factor: 3.466

2.  A Traveling Wave Ion Mobility Spectrometry (TWIMS) Study of the Robo1-Heparan Sulfate Interaction.

Authors:  Yuejie Zhao; Jeong Yeh Yang; David F Thieker; Yongmei Xu; Chengli Zong; Geert-Jan Boons; Jian Liu; Robert J Woods; Kelley W Moremen; I Jonathan Amster
Journal:  J Am Soc Mass Spectrom       Date:  2018-03-08       Impact factor: 3.109

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.  Fluorous-Tag-Assisted Synthesis of GAG-Like Oligosaccharides.

Authors:  José L de Paz; Pedro M Nieto
Journal:  Methods Mol Biol       Date:  2022

5.  Gas-Phase Analysis of the Complex of Fibroblast GrowthFactor 1 with Heparan Sulfate: A Traveling Wave Ion Mobility Spectrometry (TWIMS) and Molecular Modeling Study.

Authors:  Yuejie Zhao; Arunima Singh; Yongmei Xu; Chengli Zong; Fuming Zhang; Geert-Jan Boons; Jian Liu; Robert J Linhardt; Robert J Woods; I Jonathan Amster
Journal:  J Am Soc Mass Spectrom       Date:  2016-09-23       Impact factor: 3.109

6.  Cell-Surface Glyco-Engineering by Exogenous Enzymatic Transfer Using a Bifunctional CMP-Neu5Ac Derivative.

Authors:  Chantelle J Capicciotti; Chengli Zong; M Osman Sheikh; Tiantian Sun; Lance Wells; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2017-09-15       Impact factor: 15.419

7.  Assembly of a Complex Branched Oligosaccharide by Combining Fluorous-Supported Synthesis and Stereoselective Glycosylations using Anomeric Sulfonium Ions.

Authors:  Wei Huang; Qi Gao; Geert-Jan Boons
Journal:  Chemistry       Date:  2015-08-06       Impact factor: 5.236

8.  New glucuronic acid donors for the modular synthesis of heparan sulfate oligosaccharides.

Authors:  Omkar P Dhamale; Chengli Zong; Kanar Al-Mafraji; Geert-Jan Boons
Journal:  Org Biomol Chem       Date:  2014-02-19       Impact factor: 3.876

9.  Structural Aspects of Heparan Sulfate Binding to Robo1-Ig1-2.

Authors:  Qi Gao; Cheng-Yu Chen; Chengli Zong; Shuo Wang; Annapoorani Ramiah; Pradeep Prabhakar; Laura C Morris; Geert-Jan Boons; Kelley W Moremen; James H Prestegard
Journal:  ACS Chem Biol       Date:  2016-09-29       Impact factor: 5.100

10.  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
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