Mono-, di-, tri-, and tetra-substituted fluorotyrosines: new probes for enzymes that use tyrosyl radicals in catalysis

MR Seyedsayamdost, SY Reece…

Index: Seyedsayamdost, Mohammad R.; Reece, Steven Y.; Nocera, Daniel G.; Stubbe, JoAnne Journal of the American Chemical Society, 2006 , vol. 128, # 5 p. 1569 - 1579

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Citation Number: 106

Abstract

A set of N-acylated, carboxyamide fluorotyrosine (F n Y) analogues [Ac-3-FY-NH2, Ac-3, 5- F2Y-NH2, Ac-2, 3-F2Y-NH2, Ac-2, 3, 5-F3Y-NH2, Ac-2, 3, 6-F3Y-NH2 and Ac-2, 3, 5, 6-F4Y- NH2] have been synthesized from their corresponding amino acids to interrogate the detailed reaction mechanism (s) accessible to F n Ys in small molecules and in proteins. These Ac-F n Y-NH2 derivatives span ap K a range from 5.6 to 8.4 and a reduction ...