Stereochemistry of hydroxylation during the conversion of α-ketoisocaproate to β-hydroxyisovalerate by 4-hydroxyphenylpyruvate dioxygenase

RM Adlington, JE Baldwin, NP Croach, MH Lee…

Index: Adlington, Robert M.; Baldwin, Jack E.; Crouch, Nicholas P.; Lee, Meng-Huee; MacKinnon, Colin H.; Paul, Diana R. Bioorganic and Medicinal Chemistry Letters, 1996 , vol. 6, # 22 p. 2721 - 2724

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Citation Number: 3

Abstract

4-HPPD, Fe II, L-Ascorbate HO Ji 02, Dithio~mitol OH OH 3 4 Scheme 2 In 1990 Hart and Pascal demonstrated that ~-KICD could also convert the unnatural substrate S-4- methyl-2-oxohexanoic acid 5 to R-3-hydroxy-3-methylpentanoic acid 6, corresponding to complete retention of configuration during the hydroxylation reaction (Scheme 3) 5. In order tO establish the stereochemical outcome associated with the natural substrate 1 we have synthesized both enantiomers of the ...