Document Detail


A platform pathway for production of 3-hydroxyacids provides a biosynthetic route to 3-hydroxy-γ-butyrolactone.
MedLine Citation:
PMID:  23361005     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The replacement of petroleum feedstocks with biomass to produce platform chemicals requires the development of appropriate conversion technologies. 3-Hydroxy-γ-butyrolactone has been identified as one such chemical; however, there are no naturally occurring biosynthetic pathways for this molecule or its hydrolyzed form, 3,4-dihydroxybutyric acid. Here we design a novel pathway to produce various chiral 3-hydroxyacids, including 3,4-dihydroxybutyric acid, consisting of enzymes that condense two acyl-CoAs, stereospecifically reduce the resulting β-ketone and hydrolyze the CoA thioester to release the free acid. Acetyl-CoA serves as one substrate for the condensation reaction, whereas the second is produced intracellularly by a pathway enzyme that converts exogenously supplied organic acids. Feeding of butyrate, isobutyrate and glycolate results in the production of 3-hydroxyhexanoate, 3-hydroxy-4-methylvalerate and 3,4-dihydroxybutyric acid+3-hydroxy-γ-butyrolactone, respectively, molecules with potential uses in applications from materials to medicines. We also unexpectedly observe the condensation reaction resulting in the production of the 2,3-dihydroxybutyric acid isomer, a potential value-added monomer.
Authors:
Collin H Martin; Himanshu Dhamankar; Hsien-Chung Tseng; Micah J Sheppard; Christopher R Reisch; Kristala L J Prather
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Nature communications     Volume:  4     ISSN:  2041-1723     ISO Abbreviation:  Nat Commun     Publication Date:  2013  
Date Detail:
Created Date:  2013-01-30     Completed Date:  2013-06-20     Revised Date:  2013-09-26    
Medline Journal Info:
Nlm Unique ID:  101528555     Medline TA:  Nat Commun     Country:  England    
Other Details:
Languages:  eng     Pagination:  1414     Citation Subset:  IM    
Affiliation:
Department of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
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MeSH Terms
Descriptor/Qualifier:
4-Butyrolactone / analogs & derivatives*,  biosynthesis
Biosynthetic Pathways* / drug effects,  genetics
Escherichia coli / drug effects,  enzymology,  metabolism*
Genes, Bacterial / genetics
Glucose / metabolism
Glycolates / metabolism
Hydrochloric Acid / pharmacology
Hydroxy Acids / chemistry,  metabolism*
Isomerism
Metabolomics
Recombination, Genetic / genetics
Reproducibility of Results
Chemical
Reg. No./Substance:
0/3-hydroxy-gamma-butyrolactone; 0/Glycolates; 0/Hydroxy Acids; 50-99-7/Glucose; 7647-01-0/Hydrochloric Acid; 79-14-1/glycolic acid; 96-48-0/4-Butyrolactone
Comments/Corrections
Erratum In:
Nat Commun. 2013;4:1933

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