| Threonine aldolases-screening, properties and applications in the synthesis of non-proteinogenic beta-hydroxy-alpha-amino acids. | |
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MedLine Citation:
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PMID: 20683718 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Threonine aldolases (TAs) constitute a powerful tool for catalyzing carbon-carbon bond formations in synthetic organic chemistry, thus enabling an enantio- and diastereoselective synthesis of beta-hydroxy-alpha-amino acids. Starting from the achiral precursors glycine and an aldehyde, two new stereogenic centres are formed in this catalytic step. The resulting chiral beta-hydroxy-alpha-amino acid products are important precursors for pharmaceuticals such as thiamphenicol, a L: -threo-phenylserine derivative or L: -threo-3,4-dihydroxyphenylserine. TAs are pyridoxal-5-phosphate-dependent enzymes, which, in nature, catalyze the cleavage of L: -threonine or L: -allo-threonine to glycine and acetaldehyde in a glycine biosynthetic pathway. TAs from a broad number of species of bacteria and fungi have been isolated and characterised as biocatalysts for the synthesis of beta-hydroxy-alpha-amino acids. In this review, screening methods to obtain novel TAs, their biological function, biochemical characterisation and preparative biotransformations with TAs are described. |
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Authors:
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Nina Dückers; Katrin Baer; Sabine Simon; Harald Gröger; Werner Hummel |
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Publication Detail:
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Type: Journal Article; Review Date: 2010-08-04 |
Journal Detail:
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Title: Applied microbiology and biotechnology Volume: 88 ISSN: 1432-0614 ISO Abbreviation: Appl. Microbiol. Biotechnol. Publication Date: 2010 Sep |
Date Detail:
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Created Date: 2010-08-23 Completed Date: 2011-01-25 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 8406612 Medline TA: Appl Microbiol Biotechnol Country: Germany |
Other Details:
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Languages: eng Pagination: 409-24 Citation Subset: IM |
Affiliation:
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evocatal GmbH, Düsseldorf, Germany. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Aldehydes
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metabolism Amino Acids / biosynthesis, chemical synthesis*, chemistry Glycine / metabolism Glycine Hydroxymethyltransferase / chemistry*, classification, isolation & purification* Kinetics Recombinant Proteins / biosynthesis Threonine / metabolism |
| Chemical | |
Reg. No./Substance:
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0/Aldehydes; 0/Amino Acids; 0/Recombinant Proteins; 56-40-6/Glycine; 72-19-5/Threonine; EC 2.1.2.1/Glycine Hydroxymethyltransferase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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