Literature DB >> 20443632

Synthesis of mycobacterial triacylated phosphatidylinositol dimannoside containing an acyl lipid chain at 3-O of inositol.

Pratap S Patil1, Shang-Cheng Hung.   

Abstract

A seven-step synthesis of triacylated phosphatidylinositol dimannoside is described from myo-inositol 1,3,5-orthoformate. It proceeded in 31% overall yield via a highly regioselective and stereoselective 2,6-di-O-D-mannosylation as the key step.

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Year:  2010        PMID： 20443632     DOI： 10.1021/ol1008137

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


  7 in total

Review 1.  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

2.  Synthesis of the C-glycoside of α-(D)-mannose-(1 → 6)-(D)-myo-inositol.

Authors:  Sunej Hans; Ahmad Altiti; David R Mootoo
Journal:  Org Biomol Chem       Date:  2013-09-25       Impact factor: 3.876

Review 3.  Chemical Synthesis of Cell Wall Constituents of Mycobacterium tuberculosis.

Authors:  Mira Holzheimer; Jeffrey Buter; Adriaan J Minnaard
Journal:  Chem Rev       Date:  2021-06-30       Impact factor: 60.622

4.  Total synthesis of tetraacylated phosphatidylinositol hexamannoside and evaluation of its immunomodulatory activity.

Authors:  Pratap S Patil; Ting-Jen Rachel Cheng; Medel Manuel L Zulueta; Shih-Ting Yang; Larry S Lico; Shang-Cheng Hung
Journal:  Nat Commun       Date:  2015-06-03       Impact factor: 14.919

5.  Synthesis of a miniature lipoarabinomannan.

Authors:  Jian Gao; Guochao Liao; Lizhen Wang; Zhongwu Guo
Journal:  Org Lett       Date:  2014-01-21       Impact factor: 6.005

Review 6.  Recent Advances in the Synthesis of Glycoconjugates for Vaccine Development.

Authors:  Cinzia Colombo; Olimpia Pitirollo; Luigi Lay
Journal:  Molecules       Date:  2018-07-13       Impact factor: 4.411

7.  Diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols via chirality transfer from a glycosyl donor.

Authors:  Masamichi Tanaka; Koji Sato; Ryoki Yoshida; Nobuya Nishi; Rikuto Oyamada; Kazuki Inaba; Daisuke Takahashi; Kazunobu Toshima
Journal:  Nat Commun       Date:  2020-05-15       Impact factor: 14.919
  7 in total

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