Farnesyl diphosphate analogues with ω-bioorthogonal azide and alkyne functional groups for protein farnesyl transferase-catalyzed ligation reactions

GR Labadie, R Viswanathan…

Index: Labadie, Guillermo R.; Viswanathan, Rajesh; Poulter, C. Dale Journal of Organic Chemistry, 2007 , vol. 72, # 24 p. 9291 - 9297

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Citation Number: 40

Abstract

Eleven farnesyl diphosphate analogues, which contained ω-azide or alkyne substituents suitable for bioorthogonal Staudinger and Huisgen [3+ 2] cycloaddition coupling reactions, were synthesized. The analogues were evaluated as substrates for the alkylation of peptide cosubstrates by yeast protein farnesyl transferase. Five of the diphosphates were good alternative substrates for farnesyl diphosphate (FPP). Steady-state kinetic constants were ...