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3. One-Pot Conversion of Serine and α-Methylserine Derivatives to the Corresponding Cysteines and Selenocystines by Using Chalcogenophosphate Reagents.

Author

Makiyama, Akira, Komatsu, Itsuki, Iwaoka, Michio, and Yatagai, Masanobu

Subjects
*SERINE, *CHEMICAL reagents, *SULFUR, *SELENIUM, *AMINO acids, *ALCOHOLS (Chemical class), *THIOLS
Abstract

The one-pot reactions of N-acetylserine methyl ester and N-acetyl-α-methylserine methyl ester with Lawesson's or Woollins' reagent directly produced the corresponding cysteine or selenocysteine derivatives in moderate yields. The transformation would be initiated by phosphorylation of the hydroxy group, rather than chalcogenation of the amide group, and involve the oxazoline as a key intermediate. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT[image omitted] [ABSTRACT FROM AUTHOR]

Published
2011
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