Literature DB >> 12201708

Synthesis of 7-substituted farnesyl diphosphate analogues.

Diwan S Rawat1, Richard A Gibbs.   

Abstract

[structure: see text] Six farnesyl diphosphate analogues modified in the central isoprene unit have been prepared via our stereoselective vinyl triflate-mediated route to isoprenoids. The 7-allyl compound 6 is a modest inhibitor of mammalian protein-farnesyl transferase, but surprisingly the other five analogues are effective alternative substrates for this enzyme.

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Year:  2002        PMID： 12201708     DOI： 10.1021/ol026176i

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


  8 in total

1.  The isoprenoid substrate specificity of isoprenylcysteine carboxylmethyltransferase: development of novel inhibitors.

Authors:  Jessica L Anderson; Brian S Henriksen; Richard A Gibbs; Christine A Hrycyna
Journal:  J Biol Chem       Date:  2005-06-09       Impact factor: 5.157

2.  Synthesis and evaluation of 3- and 7-substituted geranylgeranyl pyrophosphate analogs.

Authors:  Michelle Maynor; Sarah A Scott; Emily L Rickert; Richard A Gibbs
Journal:  Bioorg Med Chem Lett       Date:  2008-02-12       Impact factor: 2.823

3.  Protein farnesyltransferase-catalyzed isoprenoid transfer to peptide depends on lipid size and shape, not hydrophobicity.

Authors:  Thangaiah Subramanian; Suxia Liu; Jerry M Troutman; Douglas A Andres; H Peter Spielmann
Journal:  Chembiochem       Date:  2008-11-24       Impact factor: 3.164

4.  Total syntheses of cyanthiwigins B, F, and G.

Authors:  John A Enquist; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-07-18       Impact factor: 5.236

5.  New synthetic methodology for the construction of 7-substituted farnesyl diphosphate analogs.

Authors:  Andrew T Placzek; Richard A Gibbs
Journal:  Org Lett       Date:  2011-06-23       Impact factor: 6.005

6.  Chemoenzymatic synthesis of an isoprenoid phosphate tool for the analysis of complex bacterial oligosaccharide biosynthesis.

Authors:  Donovan K Lujan; Jennifer A Stanziale; Anahita Z Mostafavi; Sunita Sharma; Jerry M Troutman
Journal:  Carbohydr Res       Date:  2012-07-01       Impact factor: 2.104

7.  Combinatorial modulation of protein prenylation.

Authors:  Amanda J Krzysiak; Diwan S Rawat; Sarah A Scott; June E Pais; Misty Handley; Marietta L Harrison; Carol A Fierke; Richard A Gibbs
Journal:  ACS Chem Biol       Date:  2007-05-25       Impact factor: 5.100

8.  Synthetic Routes to Methylerythritol Phosphate Pathway Intermediates and Downstream Isoprenoids.

Authors:  Sarah K Jarchow-Choy; Andrew T Koppisch; David T Fox
Journal:  Curr Org Chem       Date:  2014-04       Impact factor: 2.180
  8 in total

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