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Process for the reduction of cinnamaldehyde derivative employing enoate reductases

一种醛化合物、醚化合物的技术，应用在Z.Hamersak,,,K.Faber,Angew.Chem.Int.E领域

Inactive Publication Date: 2013-01-02
BASF SE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although β-substituted aldehydes are chirally stable, α-substituted aldehyde analogs are prone to racemization, which requires complex methods for their preparation

Method used

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  • Process for the reduction of cinnamaldehyde derivative employing enoate reductases
  • Process for the reduction of cinnamaldehyde derivative employing enoate reductases
  • Process for the reduction of cinnamaldehyde derivative employing enoate reductases

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Experimental program
Comparison scheme
Effect test

Embodiment approach

[0011] 1. In a first embodiment, the present invention provides a biocatalytic process, in particular an enzymatic catalytic process, for the production, in particular the asymmetric synthesis, of aldehyde compounds of general formula 1

[0012]

[0013] in

[0014] R 1 and R 2 represent independently of each other a linear or branched, optionally substituted alkyl group, such as C 1 -C 8 or C 1 -C 6 Alkyl; alkenyl, such as C 2 -C 8 or C 2 -C 6 Alkenyl; alkynyl, such as C 2 -C 8 or C 2 -C 6 Alkynyl; alkoxy, such as C 1 -C 8 or C 1 -C 6 Alkoxy; alkenyloxy, such as C 2 -C 8 or C 2 -C 6Alkenyloxy; -H, -OH, -SH, -halogen, such as F, Cl or Br; -NH 2 , or -NO 2 ;

[0015] In particular, H or linear or branched alkyl, such as C 1 -C 6 or C 1 -C 4 Alkyl; alkenyl, such as C 2 -C 6 Alkenyl; alkynyl, such as C 2 -C 6 Alkynyl; alkoxy, such as C 1 -C 6 or C 1 -C 4 Alkoxy; alkenyloxy, such as C 2 -C 6 Alkenyloxy; or, more specifically, H or branched C...

Embodiment 2

[0219] Embodiment 2: the bioreduction experiment that carries out with different cinnamaldehyde

[0220] route figure 1 .Asymmetric bioreduction of α-methylcinnamaldehyde derivatives 1a-3a

[0221]

[0222] 2.1 Preparation experiment

[0223] (1) General method for bioreduction of enzymes under standard conditions

[0224] Add aliquots of the enzymes (OPR1, OPR3, YqjM, OYE1-3, NCR, NEM-reductase, protein concentration in biotransformation: 75-125 µg / mL) to the cells containing the substrate (10 mM) and the cofactor NADH. (10mM) Tris-HCl buffer (0.8mL, 50mM, pH 7.5). The mixture was shaken at 30°C and 120 rpm. After 24 h, the product was extracted with EtOAc (2 x 0.5 mL). in Na 2 SO 4 The combined organic phases were dried above and analyzed respectively on achiral GC to determine conversion and on chiral GC or on HPLC to determine enantiomeric excess.

[0225] (2) General method of cofactor recycling

[0226] Aliquots of the enzyme (see above) were added to the sub...

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Abstract

The present invention relates to a novel enzymatically catalyzed method for the production of asymmetric aromatic aldehydes in an aqueous reaction medium containing certain organic co-solvents.

Description

[0001] The present invention relates to novel enzymatic catalytic methods for the production of asymmetric aromatic aldehydes in aqueous reaction media containing certain organic co-solvents. Background of the invention [0002] Due to their volatility and olfactory perception properties, aldehydes constitute important active ingredients in fragrance and fragrance applications (a) C. Chapuis, D. Jacoby, Appl. Catal. A: Gen. 2001, 221, 93-117; b) D. Pybus, C. Sell, The chemistry of fragrances, RSC Paperbacks, Royal Society of Chemistry, Cambridge, 1999). Because the enantiomers of α- and β-substituted aldehydes are often very different in odor (a) A. Abate, E. Brenna, C. Fuganti, F. G. Gatti, S. Serra, Chem. Biodivers.2004, 1, 1888-1898; b) L. Doszczak, P. Kraft, H.-P. Weber, R. Bertermann, A. Triller, H. Hatt, R. Tacke, Angew. Chem. Int. Ed. 2007, 46 , 3367-3371; c) E. Brenna, C. Fuganti, S. Serra, Tetrahedron: Asymmetry 2003, 14, 1-42), so they are usually required to be app...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/24C12P41/00
CPCC12P41/002C12P7/24
Inventor B·豪尔R·施蒂默尔C·斯蒂克勒K·费伯
Owner BASF SE
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