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US 5,393,664 AGranted
Method of preparing (S)-1-phenyl-1,3-propanediol or derivatives thereof from their respective ketones
AssigneeAjinomoto Co., Inc.
InventorsIkuo Kira, Kazuhiro Watanabe, Eiji Nakanishi, Hiroshi Ban, Norimasa Onishi, Takayuki Suzuki
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Abstract
(S)-1phenyl-1,3-propanediol or a derivative thereof having high optical purity can be produced simply in high yield, by contacting 1-phenylpropan-3-ol-1-one with a culture of microorganisms, microorganism cells isolated from the culture, or a product obtained by processing the microorganism cells.
Claims32
A method for preparing a (S)-1-phenyl-1,3-propanediol compound of formula (2), comprising contacting a compound of formula (1) ##STR3## wherein a R.sup.1 is a hydrogen atom, a halogen atom, or a C.sub.1-4 alkyl group;
- R.sup.2 is a hydrogen atom or a C.sub.1-4 -alkyl group;
- and R.sup.3 is a hydrogen atom or a C.sub.1-4 acyl group, with one member selected from the group consisting of:
- (a) a culture of a microorganism capable of asymmetrically reducing said compound of formula (1),
- (b) cells isolated from a culture of a microorganism capable of asymmetrically reducing said compound of formula (1), and
- (c) a cell product obtained from a microorganism capable of asymmetrically reducing said compound of formula (1);
- for a time sufficient to produce said (S)-1-phenyl-1,3-propanediol compound of formula (2) ##STR4## wherein R.sup.1, R.sup.2 and R.sup.3 are defined as above;
- and recovering said compound of formula (2);
- wherein said microorganism is selected from the group consisting of
- Arthrobacter paraffineus,
- Aureobacterium testaceum,
- Clavibacter michiganense,
- Enterobacter cloacae,
- Flavobacterium esteraromaticum,
- Nocardia asteroides,
- Rhodococcus erythropolis,
- Serratia marcescens,
- Candida cantarellii,
- Citeromyces matritensis,
- Cryptococcus albidus,
- Hansenula mrakii,
- Kloeckera javanica,
- Aureobasidium pullulans,
- Curvularia trifolii,
- Gelasinospora longispora,
- Monascus araneosus,
- Mucor javanicus,
- Rhizopus delemar,
- Sclerotium bataticola,
- Septoria cucurbitacearum and
- Westerdykella multispora.
27 more elements
Dependencies are inferred from the claim text.