An efficient synthesis of N-methyl amino acids by way of intermediate 5-oxazolidinones

Luigi Aurelio, John S. Box, Robert T.C. Brownlee, Andrew B. Hughes, Marianne M. Sleebs

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95 Citations (Scopus)

Abstract

N-Methyl amino acids occur in many natural products. Experimental strategies are presented for a unified approach to the synthesis of N-methyl derivatives through 5-oxazolidinones of the 20 common L-amino acids. The amino acids with reactive side chains that required protecting groups or devoted syntheses for side chain construction for N-methylation to proceed included serine, threonine, tyrosine, cysteine, methionine, tryptophan, asparagine, histidine, and arginine. The studies have provided improved methods for the preparation of N-methyl serine, threonine, and tyrosine. All 20 of the common L-amino acids are now available in suitable forms for solid or solution-phase peptide synthesis.

Original languageEnglish
Pages (from-to)2652-2667
Number of pages16
JournalThe Journal of Organic Chemistry
Volume68
Issue number7
DOIs
Publication statusPublished - 4 Apr 2003
Externally publishedYes

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