Literature DB >> 11878980

Confirmation of the connectivity of 4,8,12,16,20-pentamethylpentacosylphoshoryl beta-D-mannopyranoside, an unusual beta-mannosyl phosphoisoprenoid from Mycobacterium avium, through synthesis.

David Crich1, Vadim Dudkin.   

Abstract

The synthesis of the title glycolipid is reported. Comparison of the electrospray and high-energy collision-induced dissociation mass spectra of the synthetic material with those reported for the isolate confirm the structure of this unusual antigenic substance with its modified isoprenoid chain.

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Year:  2002        PMID: 11878980     DOI: 10.1021/ja0123958

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


  14 in total

1.  4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetals. improved second-generation acetals for the stereoselective formation of beta-D-mannopyranosides and regioselective reductive radical fragmentation to beta-D-rhamnopyranosides. scope and limitations.

Authors:  David Crich; Albert A Bowers
Journal:  J Org Chem       Date:  2006-04-28       Impact factor: 4.354

2.  Convergent synthesis of a beta-(1-->3)-mannohexaose.

Authors:  David Crich; Baolin Wu; Prasanna Jayalath
Journal:  J Org Chem       Date:  2007-08-01       Impact factor: 4.354

3.  Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors:  David Crich
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

4.  Bare-minimum fluorous mixture synthesis of a stereoisomer library of 4,8,12-trimethylnonadecanols and predictions of NMR spectra of saturated oligoisoprenoid stereoisomers.

Authors:  Edmund A-H Yeh; Eveline Kumli; Krishnan Damodaran; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2013-01-18       Impact factor: 15.419

5.  Synthesis of a beta-(1-->3)-D-rhamnotetraose by a one-pot, multiple radical fragmentation.

Authors:  David Crich; Albert A Bowers
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

Review 6.  CD1 and mycobacterial lipids activate human T cells.

Authors:  Ildiko Van Rhijn; D Branch Moody
Journal:  Immunol Rev       Date:  2015-03       Impact factor: 12.988

7.  Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups.

Authors:  David Crich; Prasanna Jayalath; Thomas K Hutton
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

8.  Synthesis and analysis of the all-(S) side chain of phosphomycoketides: a test of NMR predictions for saturated oligoisoprenoid stereoisomers.

Authors:  Jeffrey Buter; Edmund A-H Yeh; Owen W Budavich; Krishnan Damodaran; Adriaan J Minnaard; Dennis P Curran
Journal:  J Org Chem       Date:  2013-04-25       Impact factor: 4.354

9.  Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars.

Authors:  David Crich; Sébastien Picard
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

10.  CD1c presentation of synthetic glycolipid antigens with foreign alkyl branching motifs.

Authors:  Annemieke de Jong; Eva Casas Arce; Tan-Yun Cheng; Ruben P van Summeren; Ben L Feringa; Vadim Dudkin; David Crich; Isamu Matsunaga; Adriaan J Minnaard; D Branch Moody
Journal:  Chem Biol       Date:  2007-11
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