Process for producing optically active aryloxypropionic...

C - Chemistry – Metallurgy – 12 – P

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C12P 7/40 (2006.01) C07D 213/643 (2006.01) C07D 241/44 (2006.01) C07D 277/68 (2006.01) C12P 13/00 (2006.01) C12P 17/12 (2006.01) C12P 17/16 (2006.01) C12P 17/18 (2006.01) C12P 41/00 (2006.01)

Patent

CA 1230569

- 18 - ABSTRACT PROCESS FOR PRODUCING OPTICALLY ACTIVE ARYLOXYPROPIONIC ACIDS AND DERIVATIVES THEREOF ?-Aryloxypropionic acids and derivatives of formula I below are stereospecifically inverted by contact with a microorganism having a stereospecific inverting enzyme system or with that enzyme system at least partially extracted from the microorganism. This process enables the [S] enantiomer of the compound of formula I : Image (I) wherein G is ORl or Image , R1 is hydrogen or a protecting group and R2 is hydrogen or methyl, U and V each independently represent hydrogen or halogen, and R is a carboxyl group, or an enzymic equivalent thereof to be converted to the corresponding [R] enantiomer which is a useful intermediate for making the active [R] enantiomer of many herbicides. Specific microorganisms which effect the inversion are : Arthrobacter simplex (NCIB 8929); Bacillus thuringensis (NCIB 11992); Leuconostoc dextranicum (NCIB 2706); Lactobacillus plantarum (NCIB 6105); Proteus vulgaris (NCIB 67); Streptomyces sp. (NCIB 10105); Streptomyces venezuelae (ATCC 15439) and Penicillium SP (IMI 287163).

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