IP Library Granted Patent US 8,158,393
Granted Patent B2
US 8,158,393 · App. 12/159,547 · Granted Apr 17, 2012

Polypeptide having esterase activity and recombinant esterase and use thereof

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Quick Facts
Patent No.
US 8,158,393
App. No.
12/159,547
Granted
Apr 17, 2012
Kind
B2
Abstract

Method of resolving stereoselectively racemic 2-alkyl-5-halopent-4-ene-carboxylic esters of the formula (I) in which R is a C 1 -C 6 -alkyl radical, R 1 is C 1 -C 4 -alkyl and X is chlorine, bromine or iodine, by contacting a racemic ester of formula (I) with a polypeptide or recombinant protein having esterase activity and exhibiting an amino acid sequence that is at least 98% identical to the amino acid sequence of SEQ. ID. No. 1.

Claims (9)

1. A method of resolving stereoselectively racemic 2-alkyl-5-halopent-4-ene-carboxylic esters of the formula (I)

in which R is a C 1 -C 6 -alkyl radical, R 1 is C 1 -C 4 -alkyl and X is chlorine, bromine or iodine, comprising contacting a racemic ester of formula (I) with a polypeptide or recombinant protein having esterase activity and exhibiting an amino acid sequence that is at least 98% identical to the amino acid sequence of SEQ. ID. No. 1.

2. A method for preparing enantiomerically enriched 2-alkyl-5-halopent-4-enecarboxylic acids or esters thereof of the formula (II)

in which R is a C 1 -C 6 -alkyl radical, A is equal to H, R 1 , where R 1 may be C 1 -C 4 -alkyl, or R 2 , where R 2 is an alkyl group, but is not equal to R 1 , and X is chlorine, bromine or iodine, the method comprising converting a mixture of enantiomers of a 2-alkyl-5-halopent-4-enecarboxylic ester of the formula (I)

in which R, R 1 and X are as defined above,

using a polypeptide or a recombinant esterase having esterase activity and exhibiting an amino acid sequence that is at least 98% identical to the amino acid sequence of SEQ. ID. No. 1 in the presence of water or an alcohol of the formula R 2 OH, where R 2 is an alkyl group which is not equal to R 1 , as nucleophile, and isolating

a) either the remaining enantiomerically enriched 2-alkyl-5-halopent-4-enecarboxylic ester of the formula (II) with A equal to R 1 or

b) if an alcohol is employed as nucleophile, the resulting enantiomerically enriched 2-alkyl-5-halopent-4-enecarboxylic ester of the formula (II) with A equal to R 2 or

c) if water is employed as nucleophile, the resulting 2-alkyl-5-halopent-4-enecarboxylic acid of the formula (II) with A equal to H.

Assignments (4)
RELEASE (REEL 032424 / FRAME 0001) Recorded Sep 28, 2017
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
To: DSM FINE CHEMICALS AUSTRIA NFG GMBH & COKG
Reel/Frame 044037/0879 →
NOTICE OF SUCCESSION OF AGENCY FOR PATENT SECURITY INTEREST PREVIOUSLY RECORDED AT REEL/FRAME (032424/0001) Recorded Jul 12, 2017
From: UBS AG, STAMFORD BRANCH, AS PRIOR AGENT
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS SUCCESSOR AGENT
Reel/Frame 043165/0987 →
SECURITY INTEREST Recorded Mar 11, 2014
From: DSM FINE CHEMICALS AUSTRIA NFG GMBH & COKG
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 032424/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2008
From: STEINBAUER, GERHARD; STANEK, MICHEAL; POJARLIEV, PETER; SKRANC, WOLFGANG; SCHWAB, HELMUT; WUBBOLTS, MARCEL; KIERKELS, JOANNES; PICHLER, HARALD; HERMANN, MANUELA; ZENZMAIER, CHRISTOPH
To: DSM FINE CHEMICALS AUSTRIA NFG GMBH & CO KG
Reel/Frame 021798/0828 →