Document Detail

Production of chiral R-3-hydroxyalkanoic acids and R-3-hydroxyalkanoic acid methylesters via hydrolytic degradation of polyhydroxyalkanoate synthesized by pseudomonads.
MedLine Citation:
PMID:  11807767     Owner:  NLM     Status:  MEDLINE    
A novel and efficient method for the production of enantiomericaly pure R-3-hydroxyalkanoic acids and R-3-hydroxyalkanoic acid methylesters was developed. The described method is based on hydrolysis of poly(hydroxyalkanoate) copolymers synthesized by Pseudomonas putida. The polymer was isolated via solvent recovery and hydrolyzed by acid methanolysis. The obtained 3-hydroxyalkanoic acid methylester mixture was distilled into several fractions with an overall yield of 96.6% (w/w). Gas chromatography-mass spectrometry analysis of the fractions showed that 3-hydroxyhexanoic-, 3-hydroxyoctanoic-, 3 hydroxydecanoic-, and 3-hydroxydodecanoic acid methylesters were enriched to purities exceeding 96 mol%, with distillation yields of 99.9, 99.8, 88.4, and 56.8% (w/w), respectively. Subsequent saponification of the purified methylester fractions yielded the corresponding 3-hydroxyalkanoic acids, which were recovered up to 92.8% (w/w). Chiral gas chromatography analysis confirmed that both 3-hydroxyoctanoic acid and 3-hydroxyoctanoic acid methylester are present in the R-form at a very high enantiomeric excess (>99.9%).
Guy de Roo; Michele B Kellerhals; Qun Ren; Bernard Witholt; Birgit Kessler
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Publication Detail:
Type:  Journal Article; Letter; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Biotechnology and bioengineering     Volume:  77     ISSN:  0006-3592     ISO Abbreviation:  Biotechnol. Bioeng.     Publication Date:  2002 Mar 
Date Detail:
Created Date:  2002-01-24     Completed Date:  2002-05-17     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  7502021     Medline TA:  Biotechnol Bioeng     Country:  United States    
Other Details:
Languages:  eng     Pagination:  717-22     Citation Subset:  IM    
Copyright Information:
Copyright 2002 John Wiley & Sons, Inc.
Institute of Biotechnology, Swiss Federal Institute of Technology, ETH Zürich, ETH Hönggerberg HPT, CH-8093 Zürich, Switzerland.
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MeSH Terms
Hydroxy Acids / isolation & purification*
Polyesters / isolation & purification*
Pseudomonas putida / chemistry*,  metabolism*
Reg. No./Substance:
0/Hydroxy Acids; 0/Polyesters

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