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Synthesis of DL-threo-3-(1-fluoro-1-methylethyl)- and DL-threo-3-(1,1-difluoroethyl)malic acids. Machanistic studies of 3-isopropylmalate dehydrogenase

DOI: 10.1039/P19950001905

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1905 - 1912 (1995)

Update date:2022-08-05

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Authors:

Aoyama, TetsuyaAoyama, Tetsuya

Eguchi, TadashiEguchi, Tadashi

Oshima, TairoOshima, Tairo

Kakinuma, KatsumiKakinuma, Katsumi

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Article abstract of DOI:10.1039/P19950001905

For both mechanistic studies and the development of novel inhibitors of 3-isopropylmalate dehydrogenase enzyme (IPMDH), which is involved in the rate-determining step in the biosynthesis pathway of the essential amino acid L-leucine, (2R*,3S*)-3-(1-fluoro-1-methylethyl)- and (2R*,3S*)-3-(1,1-difluoroethyl)malic acids (F-IPM and F2-EM) were designed based on the concept of mechanism-based inhibition, and the reaction kinetics with these fluorinated substrates were analysed.The reaction of F-IPM with IPMDH was studied by NMR spectroscopy and product isolation.F-IPM underwent, after the normal enzyme reaction, the expected additional elimination reaction to afford an α,β-unsaturated carbonyl product, which turned out not to participate in any covalen-bond-forming reaction.The conformation of the reaction intermediate during the IPMDH reaction and the functional-group arrangement in the active site of IPMDH are discussed.

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