Journal of Organic Chemistry p. 4337 - 4345 (1983)
Update date:2022-08-04
Topics:
Nakazaki, Masao
Chikamatsu, Hiroaki
Fujii, Takeo
Sasaki, Yasuyuki
Ao, Shizuo
For elucidation of the origin of the inertness exhibited by 2-twist-brendanone type ketones 1 toward microbial and HLADH-catalyzed reductions, the stereochemistry of the oxidoreduction of 2-brendanone type ketones 5 and the related alcohols 14 was studied by preparative-scale incubation experiments.Oxidoreduction of 2-brendanone type substrates 5 and 14 by the HLADH-NAD(+) system was found to proceed with much higher rates than those of the 2-twist-brendanone type substrates 1 and 10.The steric courses found in these enzymatic processes were compared with those of microbial processes.
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