Synthesis of the Constrained L-Methionine Analog, (Z)-L-2-Amino-4-methylthio-3-butenoic Acid

Vitauts Alks; Dennis D. Keith; Janice R. Sufrin

doi:10.1055/s-1992-26177

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Synthesis 1992; 1992(7): 623-625
DOI: 10.1055/s-1992-26177

short paper

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Synthesis of the Constrained L-Methionine Analog, (Z)-L-2-Amino-4-methylthio-3-butenoic Acid

Vitauts Alks^* , Dennis D. Keith, Janice R. Sufrin

^*Grace Cancer Drug Center, Roswell Park Cancer Institute, Buffalo, New York 14263, USA

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Publication Date:
17 September 2002 (online)

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The methionine analog, (Z)-L-2-amino-4-methylthio-3-butenoic acid (1) has been synthesized. The key intermediate, (Z)-(±)-methyl 2-acetamido-4-methylthio-3-butenoate (7) was converted to 1 by enantioselective ester hydrolysis using alcalase to give (Z)-L-2-acetamido-4-methylthio-3-butenoic acid (8), followed by enzymatic removal of the N-acetyl group using hog kidney acylase.