Organic Solvent-Tolerant Marine Microorganisms as Catalysts for Kinetic Resolution of Cyclic [beta]-Hydroxy Ketones

• Published in: Marine biotechnology (New York, N.Y.) N.Y.), 2017-08, Vol.19 (4), p.351
• Main Authors: Chen, Bi -shuang, Liu, Hui, de Souza, Fayene Zeferino, Ribeiro, Liu, Lan
• Format: Article
• Language: English
• Subjects: Acetates; Biotechnology; Catalysts; Cells; Chemical synthesis; Ketones; Marine biology; Marine microorganisms; Marine sediments; Microorganisms; Natural products; Organic chemistry; Resolution; Sediment; Sediments; Solvents; Studies; Transesterification; Vinyl acetate
• ISSN: 1436-2228; 1436-2236
• DOI: 10.1007/s10126-017-9755-7

Chiral cyclic [beta]-hydroxy ketones represent key motifs in the production of natural products of biological interest. Although the molecules are structurally simple, they require cumbersome synthetic steps to get access to them and their synthesis remains a challenge in organic chemistry. In this report, we describe a straightforward approach to enantiomerically enriched (R)- and (S)-3-hydroxycyclopentanone 2a, (R)- and (S)-3-hydroxycyclohexanone 2b, and (R)- and (S)-3-hydroxycycloheptanone 2c involving a transesterification resolution of the racemates using whole cells of marine microorganisms as catalysts and vinyl acetate the acyl donor and solvent. Twenty-six strains from a wide collection of isolates from marine sediments were screened, and seven strains were found to markedly catalyze the resolution in an asymmetric fashion. Using the strain Serratia sp., (R)-2a was isolated in 27% yield with 92% ee and (S)-2a in 65% yield with 43% ee, corresponding to an E-value of 37; (R)-2b was isolated in 25% yield with 91% ee and (S)-2b in 67% yield with 39% ee, corresponding to an E-value of 40; and (R)-2c was isolated in 30% yield with 96% ee and (S)-2c in 63% yield with 63% ee, corresponding to an E-value of 75.