Literature DB >> 28696125

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

Ning Ding1, Xiuru Li, Zoeisha S Chinoy, Geert-Jan Boons2.   

Abstract

A flexible assembly strategy has been developed for the synthesis of Leishmania donovani GPI anchors that bear a clickable alkyne tag. This strategy is based on the use of the 2-naphthylmethyl (Nap) ethers and levulinoyl (Lev) ester for permanent protection of hydroxyls. Removal of seven Nap ethers by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone made it possible to prepare GPIs having an alkyne functionality that could be modified by Cu(I)-catalyzed [3 + 2] cycloadditions to install tags for imaging studies.

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Year:  2017        PMID： 28696125      PMCID： PMC5588658          DOI： 10.1021/acs.orglett.7b01703

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


  21 in total

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3.  Serum resistance of metacyclic stage Leishmania major promastigotes is due to release of C5b-9.

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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.  How to get the most out of two phosphorus chemistries. Studies on H-phosphonates.

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Journal:  Acc Chem Res       Date:  2002-11       Impact factor: 22.384

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Journal:  Mol Biochem Parasitol       Date:  2003-08-31       Impact factor: 1.759

7.  Chemoselective Cleavage of p-Methoxybenzyl and 2-Naphthylmethyl Ethers Using a Catalytic Amount of HCl in Hexafluoro-2-propanol.

Authors:  Anne Geert Volbeda; Hans A V Kistemaker; Herman S Overkleeft; Gijsbert A van der Marel; Dmitri V Filippov; Jeroen D C Codée
Journal:  J Org Chem       Date:  2015-08-14       Impact factor: 4.354

8.  CpRuIIPF6/quinaldic acid-catalyzed chemoselective allyl ether cleavage. A simple and practical method for hydroxyl deprotection.

Authors:  Shinji Tanaka; Hajime Saburi; Yoshitaka Ishibashi; Masato Kitamura
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005

Review 9.  Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research.

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Review 10.  Chemical tools for studying the biological function of glycolipids.

Authors:  Bridget L Stocker; Mattie S M Timmer
Journal:  Chembiochem       Date:  2013-06-18       Impact factor: 3.164
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4.  Rescue of Glycosylphosphatidylinositol-Anchored Protein Biosynthesis Using Synthetic Glycosylphosphatidylinositol Oligosaccharides.

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  4 in total

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