Preferred hydrolysis of methyl d-pyroglutamates (5-carbomethoxy-2-pyrrolidones) by α-chymotrypsin

Methyl d-pyroglutamate, d- III-A, is hydrolyzed by α-chymotrypsin, and the l-enantiomer is not. Methyl α-methylpyroglutamate, III-B, and methyl α-benzylpyroglutamate, III-C, are hydrolyzed by α-chymotrypsin with d-preference based on the glutamic structure, l-preference based on the alanine and phen...

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Bibliographic Details
Published inBioorganic chemistry Vol. 6; no. 3; pp. 329 - 340
Main Authors Gillan, Thomas, Mor, Gideon, Pepper, Frederick W., Cohen, Saul G.
Format Journal Article
LanguageEnglish
Published Elsevier Inc 01.01.1977
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Summary:Methyl d-pyroglutamate, d- III-A, is hydrolyzed by α-chymotrypsin, and the l-enantiomer is not. Methyl α-methylpyroglutamate, III-B, and methyl α-benzylpyroglutamate, III-C, are hydrolyzed by α-chymotrypsin with d-preference based on the glutamic structure, l-preference based on the alanine and phenylalanine structures. γ-Carbomethoxy-γ-valerolactone, IV, is hydrolyzed without stereoselectivity. Kinetics of hydrolysis of the substrates are reported. Modes of association of the substrates with the active site and the relevance of these results to the reactive orientation of the α-acylamido and hydrolyzing groups of noncyclized substrates are discussed.
ISSN:0045-2068
1090-2120
DOI:10.1016/0045-2068(77)90033-5