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Synthesis of Non-natural, Frame-Shifted Isoprenoid Diphosphate Analogues.

ABSTRACT: A set of synthetic approaches was developed and applied to the synthesis of eight frame-shifted isoprenoid diphosphate analogues. These analogues were designed to increase or decrease the methylene units between the double bonds and/or the pyrophosphate moieties of the isoprenoid structure. Evaluation of mammalian GGTase-I and FTase revealed that small structural changes can result in substantial changes in substrate activity.

SUBMITTER: Temple KJ 

PROVIDER: S-EPMC6020017 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Synthesis of Non-natural, Frame-Shifted Isoprenoid Diphosphate Analogues.

Temple Kayla J KJ   Wright Elia N EN   Fierke Carol A CA   Gibbs Richard A RA  

Organic letters 20161114 23

A set of synthetic approaches was developed and applied to the synthesis of eight frame-shifted isoprenoid diphosphate analogues. These analogues were designed to increase or decrease the methylene units between the double bonds and/or the pyrophosphate moieties of the isoprenoid structure. Evaluation of mammalian GGTase-I and FTase revealed that small structural changes can result in substantial changes in substrate activity. ...[more]

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