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Synlett 2010(19): 2941-2943  
DOI: 10.1055/s-0030-1259021
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

An Improved Method for the Preparation of Protected (R)-2-Methylcysteine: Solution-Phase Synthesis of a Glutathione Analogue

Douglas S. Masterson*a, Brant L. Kedrowskib, Amanda Blaira
a Department of Chemistry and Biochemistry, The University of Southern Mississippi, 118 College Drive #5043, Hattiesburg, MS 39406, USA
b Department of Chemistry, University of Wisconsin-Oshkosh, 800 Algoma Blvd., Oshkosh, WI 54901, USA
Fax: +1(601)2666075; e-Mail: Douglas.Masterson@usm.edu;
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Publication History

Received 22 August 2010
Publication Date:
03 November 2010 (online)

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Abstract

A synthetic method for the preparation of (R)-2-methylcysteine that dramatically improves the overall yield of this important unnatural amino acid has been refined. The key steps in the preparation of (R)-2-methylcysteine were improved such that necessary intermediates were prepared in high yields and of sufficient purity to avoid the need for distillation or column chromatography. The (R)-2-methylcysteine was prepared (>90% ee) in appropriately protected form and used in a novel solution phase synthesis of a glutathione analogue.

Key words

amino acids - asymmetric synthesis - peptides - glutathione - bioorganic chemistry