An improved synthesis of the diketopiperazine catalyst cyclo[(S)-HIS-(S)-PHE]

An improved synthesis of the diketopiperazine cyanohydrination catalyst cyclo[(S)-His-(S)-Phe] has been developed. Protection of the imidazole sidechain of histidine and a change in peptide coupling reagent results in a yield greatly increased over that of the literature procedure. In addition, simu...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1993-10, Vol.3 (10), p.2061-2062
Main Authors: Iyer, Mani S., Lipton, Mark A.
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Organic chemistry
Peptides
Preparations and properties
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Summary:An improved synthesis of the diketopiperazine cyanohydrination catalyst cyclo[(S)-His-(S)-Phe] has been developed. Protection of the imidazole sidechain of histidine and a change in peptide coupling reagent results in a yield greatly increased over that of the literature procedure. In addition, simultaneous deprotection and cyclization can be accomplished using catalytic transfer hydrogenation, providing the catalyst in three steps in overall yield of 69%. The cyclic dipeptide cyclo[(S)-His-(S)-Phe], which catalyzes the asymmetric formation of cyanohydrins from aromatic aldehydes, has been synthesized from N π-benzyl- l-histidine methyl ester in three steps in 69% overall yield.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(01)81015-5