[30293-99-3]  · C4H6N2O3  · (S)-3-Hydroxy-5-methyl-2,4-imidazolidinedione  · (MW 130.12)

(acyl activating agent for asymmetrically selective peptide synthesis1)

Alternate Name: (-)-3-hydroxy-5-methylhydantoin.

Physical Data: mp 163-164 °C; [a]D -36.0°.

Preparative Method: prepared from alanine (eq 1).1

Asymmetric Peptide Synthesis.1

The reagent activates amino acids through 1,3-Dicyclohexylcarbodiimide (DCC) coupling to the N-hydroximide for subsequent coupling with chiral amino acids. The asymmetric center induces preferential reaction with L-amino acids and high optical purities of L-L-dipeptides can be achieved (eq 2). Enantioselectivity is improved if the 5-methyl group is replaced by isobutyl.1

1. Teramoto, T.; Kurosaki, T. TL 1977, 1523.

Kenneth A. Murray

University of Cambridge, UK

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