Practical syntheses of N-substituted 3-hydroxyazetidines and 4-hydroxypiperidines by hydroxylation with Sphingomonas sp. HXN-200.
[reaction: see text] Hydroxylation of N-substituted azetidines 11 and 12 and piperidines 15-19 with Sphingomonas sp. HXN-200 gave 91-98% of the corresponding 3-hydroxyazetidines 13 and 14 and 4-hydroxypiperidines 20-24, respectively, with high activity and excellent regioselectivity. High yields and high product concentrations (2 g/L) were achieved with frozen/thawed cells as biocatalyst. For the first time, rehydrated lyophilized cells were successfully used for the biohydroxylation.
Chang
Dongliang
D
Institute of Biotechnology, ETH-Hönggerberg, CH-8093 Zürich, Switzerland.
Feiten
Hans-Jürgen
HJ
Engesser
Karl-H
KH
van Beilen
Jan B
JB
Witholt
Bernard
B
Li
Zhi
Z
D000447:Aldehydes / Q000138:chemical synthesis; D001384:Azetidines / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D005692:Galactose Oxidase / Q000737:chemistry*; D006898:Hydroxylamines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D008970:Molecular Weight; D010091:Oximes / Q000138:chemical synthesis; D010880:Piperidines / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis
D000447:Aldehydes; D001384:Azetidines; D006898:Hydroxylamines; D010091:Oximes; D010880:Piperidines; D011108:Polymers; D005692:Galactose Oxidase