Synthesis of Chiral Epihalohydrins Using Haloalcohol Dehalogenase A from Arthrobacter Erithii H10a

Investigation of the epoxide enantiomers formed by the action of the haloalcohol dehalogenase from Arthrobacter erithii H10a revealed that ( r)-epichlorohydrin (ECH) was selectively produced from 1,3-dichloro-2-propanol (1,3-DCP). A maximum enantiomeric excess (e.e. > 95%) of ( r)-ECH was obtaine...

Full description

Saved in:
Bibliographic Details
Published in:Enzyme and microbial technology 1998-05, Vol.22 (7), p.545-551
Main Authors: Assis, H.M.S, Bull, A.T, Hardman, D.J
Format: Article
Language:English
Subjects:
Alcohols
Arthrobacter erithii
Arthrobacter erithii H10a
Bacteria
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Chlorination
Chlorine compounds
Dehalogenation
enantioselective dehalogenation
enantioselective halogenation
Enzymes
Fundamental and applied biological sciences. Psychology
haloalcohol dehalogenase
Methods. Procedures. Technologies
Optically active epihalohydrins
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Investigation of the epoxide enantiomers formed by the action of the haloalcohol dehalogenase from Arthrobacter erithii H10a revealed that ( r)-epichlorohydrin (ECH) was selectively produced from 1,3-dichloro-2-propanol (1,3-DCP). A maximum enantiomeric excess (e.e. > 95%) of ( r)-ECH was obtained when dehalogenation of 1,3-DCP occurred in the presence of an excess of KBr. During the reverse reaction, ( r)-ECH was stereoselectively halogenated to form 1,3-DCP if the halogen in the reaction mixture was chloride; however, if chloride was substituted by bromide, the ( s)-isomer was halogenated preferentially, resulting in the accumulation of the ( r)-isomer. ( r)-epibromohydrin (EBH) was formed as the result of transhalogenation. If the starting substrates were EBH and KCl, the ( r)-isomer was selectively chlorinated while the transhalogenation product was ( s)-ECH.
ISSN:0141-0229
1879-0909
DOI:10.1016/S0141-0229(97)00255-X