Literature DB >> 10937743

Grignard-mediated synthesis and preliminary biological evaluation of novel 3-substituted farnesyl diphosphate analogues.

T J Zahn1, C Weinbaum, R A Gibbs.   

Abstract

A series of substituents was installed at the 3 position of farnesyl diphosphate through a copper-cyanide mediated coupling of a vinyl triflate with various Grignard reagents. These novel FPP mimetics were then evaluated as inhibitors of or substrates for mammalian protein farnesyl transferase. The IC50 values for these compounds range from 18 to 10,100 nm, with the 3-isopropenyl analogue being one of the most potent FPP-mimetic mFTase inhibitors yet synthesized.

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Year:  2000        PMID: 10937743     DOI: 10.1016/s0960-894x(00)00337-1

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  6 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 synthesis and structure-activity relationship study of the potent cAMP signaling agonist (-)-alotaketal A.

Authors:  Jinhua Huang; Jessica R Yang; Jin Zhang; Jiong Yang
Journal:  Org Biomol Chem       Date:  2013-04-12       Impact factor: 3.876

5.  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

6.  Total synthesis of the potent cAMP signaling agonist (-)-alotaketal A.

Authors:  Jinhua Huang; Jessica R Yang; Jin Zhang; Jiong Yang
Journal:  J Am Chem Soc       Date:  2012-05-16       Impact factor: 15.419

  6 in total

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