Tetrahedron p. 3537 - 3544 (1997)
Update date:2022-08-03
Topics:
Chiba, Akira
Eguchi, Tadashi
Oshima, Tairo
Kakinuma, Katsumi
The finding that 2-O-methyl-3-isopropylmalate was an uncompetitive inhibitor of 3-isopropylmalate dehydrogenase (IPMDH, EC 1.1.1.85), involved in the rate-determining step in the biosynthetic pathway of the essential amino acid L-leucine, prompted to design conformationally restricted substrate analogs, in which the hydroxy oxygen is intramolecularly bound to an isopropyl carbon to form a ring structure. The oxirane 2 was the most inhibitory among those synthesized. IPMDH appeared to recognize preferentially the anti-conformation of the butanedioic acid structure.
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(1968)