Appl Environ Microbiol. 1992 May;58(5):1699-704.

Acyloin formation by benzoylformate decarboxylase from Pseudomonas putida.

Wilcocks R, Ward OP, Collins S, Dewdney NJ, Hong Y, Prosen E.

Source

Department of Biology, University of Waterloo, Ontario, Canada.

Abstract

Whole cells and cell extracts of Pseudomonas putida grown in a medium containing ammonium mandelate have the capacity to produce the acyloin compound 2-hydroxypropiophenone when incubated with benzoylformate and acetaldehyde. Benzaldehyde and benzyl alcohol were formed as reaction by-products. The enantiomeric excess of the 2-hydroxypropiophenone product was found to be 91 to 92%. The absolute configuration of the enzymatically prepared product at the carbinol carbon was found to be S. The thiamine PPi-linked enzyme benzoylformate decarboxylase, purified to give a single protein band on polyacrylamide gel electrophoresis, was shown to be responsible for the catalysis of this novel condensation reaction.

PMID:: 1622241; [PubMed - indexed for MEDLINE]
PMCID:: PMC195660

Free PMC Article

Publication Types, MeSH Terms, Substances

Publication Types

Research Support, Non-U.S. Gov't

MeSH Terms

Substances

LinkOut - more resources

Full Text Sources

Molecular Biology Databases

BENZALDEHYDE - HSDB

Supplemental Content

Save items

Related citations in PubMed

Influence of the hydrostatic pressure and pH on the asymmetric 2-hydroxyketone formation catalyzed by Pseudomonas putida benzoylformate decarboxylase and variants thereof. [Biotechnol Bioeng. 2010]
Influence of the hydrostatic pressure and pH on the asymmetric 2-hydroxyketone formation catalyzed by Pseudomonas putida benzoylformate decarboxylase and variants thereof.
Berheide M, Peper S, Kara S, Long WS, Schenkel S, Pohl M, Niemeyer B, Liese A. Biotechnol Bioeng. 2010 May 1; 106(1):18-26.
Identification of novel benzoylformate decarboxylases by growth selection. [Appl Environ Microbiol. 2006]
Identification of novel benzoylformate decarboxylases by growth selection.
Henning H, Leggewie C, Pohl M, Müller M, Eggert T, Jaeger KE. Appl Environ Microbiol. 2006 Dec; 72(12):7510-7. Epub 2006 Sep 29.
Factors affecting 2-hydroxypropiophenone formation by benzoylformate decarboxylase from Pseudomonas putida. [Biotechnol Bioeng. 1992]
Factors affecting 2-hydroxypropiophenone formation by benzoylformate decarboxylase from Pseudomonas putida.
Wilcocks R, Ward OP. Biotechnol Bioeng. 1992 Apr 25; 39(10):1058-63.
Review New enzymes for biotransformations. [Curr Opin Chem Biol. 2005]
Review New enzymes for biotransformations.
Faber K, Kroutil W. Curr Opin Chem Biol. 2005 Apr; 9(2):181-7.
Review Enzymatic asymmetric synthesis by decarboxylases. [Curr Opin Biotechnol. 2000]
Review Enzymatic asymmetric synthesis by decarboxylases.
Ward OP, Singh A. Curr Opin Biotechnol. 2000 Dec; 11(6):520-6.

See reviews... See all...

Cited by 2 PubMed Central articles

Physiological relation between respiration activity and heterologous expression of selected benzoylformate decarboxylase variants in Escherichia coli. [Microb Cell Fact. 2010]
Physiological relation between respiration activity and heterologous expression of selected benzoylformate decarboxylase variants in Escherichia coli.
Palmen TG, Nieveler J, Frölich B, Treffenfeldt W, Pohl M, Büchs J. Microb Cell Fact. 2010 Oct 19; 9:76. Epub 2010 Oct 19.
Purification and crystallization of benzoylformate decarboxylase. [Protein Sci. 1995]
Purification and crystallization of benzoylformate decarboxylase.
Hasson MS, Muscate A, Henehan GT, Guidinger PF, Petsko GA, Ringe D, Kenyon GL. Protein Sci. 1995 May; 4(5):955-9.

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
Compound (MeSH Keyword)
PubChem chemical compound records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
References for this PMC Article
Citation referenced in PubMed article. Only valid for PubMed citations that are also in PMC.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Free in PMC
Free full text articles in PMC
Cited in PMC
Full-text articles in the PubMed Central Database that cite the current articles.

Recent activity

Clear Turn Off Turn On

Acyloin formation by benzoylformate decarboxylase from Pseudomonas putida.
Acyloin formation by benzoylformate decarboxylase from Pseudomonas putida.
Appl Environ Microbiol. 1992 May ;58(5):1699-704.

PubMed
Creatine monohydrate and resistance training increase bone mineral content and d...
Creatine monohydrate and resistance training increase bone mineral content and density in older men.
J Nutr Health Aging. 2005 Sep-Oct ;9(5):352-3.

PubMed
Cytokinesis failure generating tetraploids promotes tumorigenesis in p53-null ce...
Cytokinesis failure generating tetraploids promotes tumorigenesis in p53-null cells.
Nature. 2005 Oct 13 ;437(7061):1043-7.

PubMed
Prediction of tumor-brain adhesion in intracranial meningiomas by MR imaging and...
Prediction of tumor-brain adhesion in intracranial meningiomas by MR imaging and DSA.
Magn Reson Med Sci. 2003 Dec 31 ;2(4):171-9.

PubMed
The impact of obesity on primary care visits.
The impact of obesity on primary care visits.
Obes Res. 2005 Sep ;13(9):1615-23.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to: