Abstract
Farnesyl diphosphate (FPP) is an important metabolic intermediate in the biosynthesis of a variety of molecules including sesquiterpenes and the side chains of a number of cofactors. FPP is also the source of isoprenoid side chains found attached to proteins. Enzymes that employ FPP as a substrate are of interest because they are involved in the semisynthesis of drugs as well as targets for drug design. Photoactive analogs of FPP have been useful for identifying enzymes that use this molecule as a substrate. A variety of photocrosslinking groups have been employed to prepare FPP analogs for use in such experiments including aryl azides, diazotrifluoropropionates and benzophenones. In this review, the design of these probes is described along with an examination of how they have been used in crosslinking experiments.
Keywords: Aryl azide, benzophenone, diazoester, farnesyl diphosphate, farnesyl diphosphate synthase, geranylgeranyl diphosphate, photoaffinity labeling, photocrosslinking, protein farnesyltransferase, sesquiterpene cyclase
Current Medicinal Chemistry
Title:Photoactive Analogs of Farnesyl Diphosphate and Related Isoprenoids: Design and Applications in Studies of Medicinally Important Isoprenoid- Utilizing Enzymes
Volume: 20 Issue: 12
Author(s): Jeffrey S. Vervacke, Yen-Chih Wang and Mark D. Distefano
Affiliation:
Keywords: Aryl azide, benzophenone, diazoester, farnesyl diphosphate, farnesyl diphosphate synthase, geranylgeranyl diphosphate, photoaffinity labeling, photocrosslinking, protein farnesyltransferase, sesquiterpene cyclase
Abstract: Farnesyl diphosphate (FPP) is an important metabolic intermediate in the biosynthesis of a variety of molecules including sesquiterpenes and the side chains of a number of cofactors. FPP is also the source of isoprenoid side chains found attached to proteins. Enzymes that employ FPP as a substrate are of interest because they are involved in the semisynthesis of drugs as well as targets for drug design. Photoactive analogs of FPP have been useful for identifying enzymes that use this molecule as a substrate. A variety of photocrosslinking groups have been employed to prepare FPP analogs for use in such experiments including aryl azides, diazotrifluoropropionates and benzophenones. In this review, the design of these probes is described along with an examination of how they have been used in crosslinking experiments.
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Cite this article as:
S. Vervacke Jeffrey, Wang Yen-Chih and D. Distefano Mark, Photoactive Analogs of Farnesyl Diphosphate and Related Isoprenoids: Design and Applications in Studies of Medicinally Important Isoprenoid- Utilizing Enzymes, Current Medicinal Chemistry 2013; 20 (12) . https://dx.doi.org/10.2174/0929867311320120008
DOI https://dx.doi.org/10.2174/0929867311320120008 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
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