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Process for producing optically active phenylalanine compounds from cinnamic acid derivatives using phenylalanine ammonia-lyase derived from idiomarina loihiensis

A technology of phenylalanine ammonia lyase and phenylalanine, which is applied in fermentation and other directions, and can solve the problem of unattractiveness

Inactive Publication Date: 2019-01-04
DPX HLDG
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, in order to produce acceptable quantities of product, large volumes or complex feeding schemes are required, making the process less attractive from a commercial point of view

Method used

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  • Process for producing optically active phenylalanine compounds from cinnamic acid derivatives using phenylalanine ammonia-lyase derived from idiomarina loihiensis
  • Process for producing optically active phenylalanine compounds from cinnamic acid derivatives using phenylalanine ammonia-lyase derived from idiomarina loihiensis
  • Process for producing optically active phenylalanine compounds from cinnamic acid derivatives using phenylalanine ammonia-lyase derived from idiomarina loihiensis

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Embodiment

[0049] The following clones were used in the test of PAL activity.

[0050]

[0051]

[0052] The gene with the nucleic acid sequence given above was amplified by PCR, and the purified PCR product was fused with the NcoI and BglII sites of the vector pSE420 (Invitrogen Corp. CA USA) using the Xi cloning method. By using this method, the NcoI site is destroyed after the gene is cloned. The resulting plasmid was transformed into E.coli TOP 10 cells (Invitrogen), and checked for correct insertion by restriction analysis and agarose gel electrophoresis, and the clone number (clonenumber) given above was given.

[0053] The PAL gene of R. glutinis was synthesized by Genscript Corporation, Scotch Plains, USA according to the protein sequence of PAL of Rhodosporidium toruloides ATCC 10788, and its sequence is listed under the number CAA31209 in the NCBI protein database. The codons of the synthesized PAL gene are optimized for expression in E. coli. The synthesized gene was ligated into...

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Abstract

The invention relates to a process for the preparation of an enantiomerically enriched phenylalanine compound by reacting the corresponding cinnamic acid with an amino group donor in the presence of a stereoselective phenylalanine ammonia lyase having a sequence identity of at least 50% with SEQ ID NO. 4 (amino acid sequence of PAL from ldiomarina loihiensis).

Description

[0001] This application is a divisional application of the Chinese patent application with application number 200780033815.8. The original application is a Chinese national phase application of the international application PCT / EP2007 / 007945. Technical field [0002] The present invention relates to a method for preparing an enantiomerically enriched phenylalanine compound, wherein the corresponding cinnamic acid is reacted with an amino donor in the presence of a stereoselective phenylalanine ammonia lyase. Background technique [0003] Enantiomerically enriched phenylalanine compounds are important intermediates for pharmaceutical products, especially in the preparation of angiotensin I converting enzyme inhibitors (ACE). ACE is used to treat hypertension (high blood pressure, also called hypertension). For example, optically active (S)-indoline-2-carboxylic acid ((S)-indoline-2-carboxylicacid) (which can be prepared by ring closure of (S)-2-chlorophenylalanine) can be used to p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P13/22
CPCC12P13/222
Inventor 弗里斯科·伯纳德·简·范 阿斯玛纳特斯卡·斯里尼吉
Owner DPX HLDG
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