Literature DB >> 15058979

Imino-C-nucleoside synthesis: heteroaryl lithium carbanion additions to a carbohydrate cyclic imine and nitrone.

Gary B Evans1, Richard H Furneaux, Herwig Hausler, Janus S Larsen, Peter C Tyler.   

Abstract

Promotion by Lewis acid of the addition of some aryllithiums to a carbohydrate-based imine, which has allowed a more facile synthesis of some imino-C-nucleoside analogues, is described. Use of the corresponding nitrone does not assist in some cases, but lithiated acetonitrile adds to it efficiently to give a product from which further C-nucleoside analogues can be derived.

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Year:  2004        PMID： 15058979     DOI： 10.1021/jo035744k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Synthesis of bis-Phosphate Iminoaltritol Enantiomers and Structural Characterization with Adenine Phosphoribosyltransferase.

Authors:  Lawrence D Harris; Rajesh K Harijan; Rodrigo G Ducati; Gary B Evans; Brett M Hirsch; Vern L Schramm
Journal:  ACS Chem Biol       Date:  2017-12-14       Impact factor: 5.100

2.  Structure and inhibition of a quorum sensing target from Streptococcus pneumoniae.

Authors:  Vipender Singh; Wuxian Shi; Steven C Almo; Gary B Evans; Richard H Furneaux; Peter C Tyler; Gavin F Painter; Dirk H Lenz; Simon Mee; Renjian Zheng; Vern L Schramm
Journal:  Biochemistry       Date:  2006-10-31       Impact factor: 3.162

3.  Transition state analogues of Plasmodium falciparum and human orotate phosphoribosyltransferases.

Authors:  Yong Zhang; Gary B Evans; Keith Clinch; Douglas R Crump; Lawrence D Harris; Richard F G Fröhlich; Peter C Tyler; Keith Z Hazleton; María B Cassera; Vern L Schramm
Journal:  J Biol Chem       Date:  2013-10-24       Impact factor: 5.157

4.  Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring.

Authors:  Venkata L A Malladi; Adam J Sobczak; Tiffany M Meyer; Dehua Pei; Stanislaw F Wnuk
Journal:  Bioorg Med Chem       Date:  2011-07-28       Impact factor: 3.641

5.  Distortional binding of transition state analogs to human purine nucleoside phosphorylase probed by magic angle spinning solid-state NMR.

Authors:  Mathew J Vetticatt; Boris Itin; Gary B Evans; Vern L Schramm
Journal:  Proc Natl Acad Sci U S A       Date:  2013-09-16       Impact factor: 11.205

6.  Direct synthesis of imino-C-nucleoside analogues and other biologically active iminosugars.

Authors:  Milan Bergeron-Brlek; Michael Meanwell; Robert Britton
Journal:  Nat Commun       Date:  2015-04-23       Impact factor: 14.919
  6 in total

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