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Synthesis of frame-shifted farnesyl diphosphate analogs.

ABSTRACT: A set of synthetic approaches were developed and applied to the synthesis of eight frame-shifted farnesyl diphosphate (FPP) analogs. These analogs bear increased or decreased methylene units between the double bonds and/or diphosphate moieties of the isoprenoid structure. Evaluation versus mammalian FTase revealed that small structural changes can lead to dramatic changes in substrate ability.

SUBMITTER: Placzek AT

PROVIDER: S-EPMC6863160 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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Synthesis of frame-shifted farnesyl diphosphate analogs.

Placzek Andrew T AT Hougland James L JL Gibbs Richard A RA

Organic letters 20120802 16

A set of synthetic approaches were developed and applied to the synthesis of eight frame-shifted farnesyl diphosphate (FPP) analogs. These analogs bear increased or decreased methylene units between the double bonds and/or diphosphate moieties of the isoprenoid structure. Evaluation versus mammalian FTase revealed that small structural changes can lead to dramatic changes in substrate ability. ...[more]

PMID: 22857735

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