Literature DB >> 20423078

Synthesis of a glycosylphosphatidylinositol anchor bearing unsaturated lipid chains.

Benjamin M Swarts1, Zhongwu Guo.   

Abstract

A GPI anchor bearing unsaturated fatty acid lipid chains (1) was synthesized by a highly convergent strategy employing the para-methoxybenzyl group for permanent hydroxyl protection. The final global deprotection was achieved by an efficient three-step, one-pot procedure to give an 81% isolated yield of the target structure.

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Year:  2010        PMID： 20423078      PMCID： PMC2873617          DOI： 10.1021/ja1009037

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  12 in total

1.  Rapid synthesis of a glycosylphosphatidylinositol-based malaria vaccine using automated solid-phase oligosaccharide synthesis.

Authors:  Michael C Hewitt; Daniel A Snyder; Peter H Seeberger
Journal:  J Am Chem Soc       Date:  2002-11-13       Impact factor: 15.419

2.  The chemical synthesis of bioactive glycosylphosphatidylinositols from Trypanosoma cruzi containing an unsaturated fatty acid in the lipid.

Authors:  Dmitry V Yashunsky; Vladimir S Borodkin; Michael A J Ferguson; Andrei V Nikolaev
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-09       Impact factor: 15.336

3.  Highly purified glycosylphosphatidylinositols from Trypanosoma cruzi are potent proinflammatory agents.

Authors:  I C Almeida; M M Camargo; D O Procópio; L S Silva; A Mehlert; L R Travassos; R T Gazzinelli; M A Ferguson
Journal:  EMBO J       Date:  2000-04-03       Impact factor: 11.598

4.  A new approach to construct full-length glycosylphosphatidylinositols of parasitic protozoa and [4-deoxy-Man-III]-GPI analogues.

Authors:  Asif Ali; D Channe Gowda; Ram A Vishwakarma
Journal:  Chem Commun (Camb)       Date:  2004-12-02       Impact factor: 6.222

5.  Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides.

Authors:  David Crich; Abhisek Banerjee
Journal:  J Am Chem Soc       Date:  2006-06-21       Impact factor: 15.419

6.  Glycosyl-phosphatidylinositol moiety that anchors Trypanosoma brucei variant surface glycoprotein to the membrane.

Authors:  M A Ferguson; S W Homans; R A Dwek; T W Rademacher
Journal:  Science       Date:  1988-02-12       Impact factor: 47.728

Review 7.  The structure and biosynthesis of glycosyl phosphatidylinositol protein anchors.

Authors:  P T Englund
Journal:  Annu Rev Biochem       Date:  1993       Impact factor: 23.643

8.  Inositolphosphoglycan mediators structurally related to glycosyl phosphatidylinositol anchors: synthesis, structure and biological activity.

Authors:  M Martín-Lomas; N Khiar; S García; J L Koessler; P M Nieto; T W Rademacher
Journal:  Chemistry       Date:  2000-10-02       Impact factor: 5.236

9.  Convergent synthesis of a GPI containing an acylated inositol.

Authors:  Jie Xue; Zhongwu Guo
Journal:  J Am Chem Soc       Date:  2003-12-31       Impact factor: 15.419

Review 10.  The glycosylphosphatidylinositol anchor: a complex membrane-anchoring structure for proteins.

Authors:  Margot G Paulick; Carolyn R Bertozzi
Journal:  Biochemistry       Date:  2008-06-17       Impact factor: 3.162
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  14 in total

1.  Chemical synthesis and functionalization of clickable glycosylphosphatidylinositol anchors.

Authors:  Benjamin M Swarts; Zhongwu Guo
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

2.  Synthetic Studies of Glycosylphosphatidylinositol (GPI) Anchors and GPI-Anchored Peptides, Glycopeptides, and Proteins.

Authors:  Zhongwu Guo
Journal:  Curr Org Synth       Date:  2013-06-01       Impact factor: 1.975

Review 3.  Recent progress in synthetic and biological studies of GPI anchors and GPI-anchored proteins.

Authors:  Shichong Yu; Zhongwu Guo; Charlie Johnson; Guofeng Gu; Qiuye Wu
Journal:  Curr Opin Chem Biol       Date:  2013-10-12       Impact factor: 8.822

Review 4.  Chemical synthesis of glycosylphosphatidylinositol anchors.

Authors:  Benjamin M Swarts; Zhongwu Guo
Journal:  Adv Carbohydr Chem Biochem       Date:  2012       Impact factor: 12.200

Review 5.  Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for 2009-2010.

Authors:  David J Harvey
Journal:  Mass Spectrom Rev       Date:  2014-05-26       Impact factor: 10.946

6.  Synthesis of a Glycosylphosphatidylinositol Anchor Derived from Leishmania donovani That Can Be Functionalized by Cu-Catalyzed Azide-Alkyne Cycloadditions.

Authors:  Ning Ding; Xiuru Li; Zoeisha S Chinoy; Geert-Jan Boons
Journal:  Org Lett       Date:  2017-07-11       Impact factor: 6.005

7.  Total synthesis of a glycosylphosphatidylinositol anchor of the human lymphocyte CD52 antigen.

Authors:  Srinivas Burgula; Benjamin M Swarts; Zhongwu Guo
Journal:  Chemistry       Date:  2011-12-21       Impact factor: 5.236

8.  Advances in the Chemical Synthesis of Carbohydrates and Glycoconjugates.

Authors:  Ankita Malik; Peter H Seeberger; Daniel Varón Silva
Journal:  Adv Biochem Eng Biotechnol       Date:  2021       Impact factor: 2.635

9.  Chemical Synthesis of GPI Glycan-Peptide Conjugates by Traceless Staudinger Ligation.

Authors:  Sanyong Zhu; Zhongwu Guo
Journal:  Org Lett       Date:  2017-05-25       Impact factor: 6.005

10.  Synthesis of a tristearoyl lipomannan via preactivation-based iterative one-pot glycosylation.

Authors:  Jian Gao; Zhongwu Guo
Journal:  J Org Chem       Date:  2013-12-03       Impact factor: 4.354
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