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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Published in | Bioorganic chemistry Vol. 6; no. 3; pp. 329 - 340 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Elsevier Inc
01.01.1977
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Online Access | Get full text |
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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. |
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ISSN: | 0045-2068 1090-2120 |
DOI: | 10.1016/0045-2068(77)90033-5 |