Stereo-complementary bioreduction of saturated N-heterocyclic ketones. (May 2017)

• Record Type: Journal Article
• Authors: Li, Chao; Liu, Yan; Pei, Xiao-Qiong; Wu, Zhong-Liu
• Is Part Of: Process biochemistry. Volume 56(2017)
• Page Start: 90
• Page End: 97
• Publication Date: 2017-05
• Subjects: Ketoreductase -- Hydroxypiperidine -- Hydroxypyrrolidine -- Hydroxyazepane -- Bioreduction; tert-butyl 3-oxopyrrolidine-1-carboxylate (PubChem CID: 471360) -- (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (PubChem CID: 854055) -- (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (PubChem CID: 6544479) -- 1-benzylpyrrolidin-3-one (PubChem CID: 69890) -- (S)-1-benzylpyrrolidin-3-ol (PubChem CID: 2733875) ;(R)-1-benzylpyrrolidin-3-ol (PubChem CID: 643472) -- benzyl 3-oxopyrrolidine-1-carboxylate (PubChem CID: 561203) -- (S)-benzyl 3-hydroxypyrrolidine-1-carboxylate (PubChem CID: 13438604) -- (R)-benzyl 3-hydroxypyrrolidine-1-carboxylate (PubChem CID: 11183628) -- ethyl 3-oxopyrrolidine-1-carboxylate (PubChem CID: 277754) -- (S)-ethyl 3-hydroxypyrrolidine-1-carboxylate (PubChem CID: 66772749) -- (R)-ethyl 3-hydroxypyrrolidine-1-carboxylate (PubChem CID: 66291444) -- tert-butyl 3-oxopiperidine-1-carboxylate (PubChem CID: 2756825) -- (S)-tert-butyl 3-hydroxypiperidine-1-carboxylate (PubChem CID: 1514399) -- (R)-tert-butyl 3-hydroxypiperidine-1-carboxylate (PubChem CID: 1514398) -- 1-benzylpiperidin-3-one (PubChem CID: 96650) -- (S)-1-benzylpiperidin-3-ol (PubChem CID: 693762) -- (R)-1-benzylpiperidin-3-ol (PubChem CID: 693761) -- benzyl 3-oxopiperidine-1-carboxylate (PubChem CID: 1514169) -- (S)-benzyl 3-hydroxypiperidine-1-carboxylatel (PubChem CID: 6932653) -- (R)-benzyl 3-hydroxypiperidine-1-carboxylate (PubChem CID: 6932652) -- tert-butyl 4-oxoazepane-1-carboxylate (PubChem CID: 1512679) -- (S)-tert-butyl 4-hydroxyazepane-1-carboxylate (PubChem CID: 40481276) -- (R)-tert-butyl 4-hydroxyazepane-1-carboxylate (PubChem CID: 40481277) -- 1-benzylazepan-4-one (PubChem CID: 1514350) -- (S)-1-benzylazepan-4-ol (PubChem CID: 1514352) -- (R)-1-benzylazepan-4-ol (PubChem CID: 1514351) -- benzyl 4-oxoazepane-1-carboxylate (PubChem CID: 1512681) -- (S)-benzyl 4-hydroxyazepane-1-carboxylate (PubChem CID: 51892891) -- (R)-benzyl 4-hydroxyazepane-1-carboxylate (PubChem CID: 51892892) -- tert-butyl 3-oxoazepane-1-carboxylate (PubChem CID: 22831870) -- (S)-tert-butyl 3-hydroxyazepane-1-carboxylate (PubChem CID: 73424851) -- (R)-tert-butyl 3-hydroxyazepane-1-carboxylate (PubChem CID: 73424814) -- 1-benzylazepan-3-one (PubChem CID: 15152264) -- 1-benzylazepan-3-ol (PubChem CID: 22933843).; Biochemical engineering -- Periodicals; Biotechnology -- Periodicals; Biochemistry -- periodicals; Biotechnology -- periodicals; Chemical Engineering -- periodicals; Génie biochimique -- Périodiques; Biotechnologie -- Périodiques; Biochemical engineering; Biotechnology; Periodicals; 660.63
• DOI: 10.1016/j.procbio.2017.03.002
• Languages: English
• ISSNs: 1359-5113

Abstract

Highlights: Ketoreductases READH and Ch KRED20 were applied in asymmetric bioreduction. Saturated N -heterocyclic ketones with a five- to seven-membered ring were reduced. Stereo-complementary reduction was achieved with excellent selectivity. Isopropanol was used as both the ultimate reducing agent and co-solvent. Abstract: The asymmetric bioreduction of several saturated N -heterocyclic ketones is demonstrated in a stereo-complementary fashion using the ketoreductases READH and Ch KRED20 for the production of ( S )- and ( R )-alcohols, respectively. The reaction accepts substrates with a five-, six- or seven-membered ring, and exhibits excellent stereoselectivity when using 2-propanol as both the ultimate reducing agent and cosolvent, achieve >99% ee in the majority of cases for both enantiomers.