Microbial Synthesis of the Energetic Material Precursor 1,2,4-Butanetriol

Wei Niu, Mapitso N. Molefe, J. W. Frost

Research output: Contribution to journalArticle

117 Citations (Scopus)

Abstract

The lack of a route to precursor 1,2,4-butanetriol that is amenable to large-scale synthesis has impeded substitution of 1,2,4-butanetriol trinitrate for nitroglycerin. To identify an alternative to the current commercial synthesis of racemic D,L-1,2,4-butanetriol involving NaBH4 reduction of esterified D,L-malic acid, microbial syntheses of D- and L-1,2,4-butanetriol have been established. These microbial syntheses rely on the creation of biosynthetic pathways that do not exist in nature. Oxidation of D-xylose by Pseudomonas fragi provides D-xylonic acid in 70% yield. Escherichia coli DH5α/pWN6.186A then catalyzes the conversion of D-xylonic acid into D-1,2,4-butanetriol in 25% yield. P. fragi is also used to oxidize L-arabinose to a mixture of L-arabino-1,4-lactone and L-arabinonic acid in 54% overall yield. After hydrolysis of the lactone, L-arabinonic acid is converted to L-1,2,4-butanetriol in 35% yield using E. coli BL21(DE3)/pWN6.222A. As a catalytic route to 1,2,4-butanetriol, microbial synthesis avoids the high H2 pressures and elevated temperatures required by catalytic hydrogenation of malic acid.

Original languageEnglish (US)
Pages (from-to)12998-12999
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number43
DOIs
StatePublished - Oct 29 2003

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Acids
Pseudomonas fragi
Escherichia coli
Xylose
Arabinose
Hydrogenation
Biosynthetic Pathways
Nitroglycerin
Lactones
1,2,4-butanetriol
1,3,4-butanetriol
Hydrolysis
Substitution reactions
Oxidation
Pressure
Temperature
malic acid

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Microbial Synthesis of the Energetic Material Precursor 1,2,4-Butanetriol. / Niu, Wei; Molefe, Mapitso N.; Frost, J. W.

In: Journal of the American Chemical Society, Vol. 125, No. 43, 29.10.2003, p. 12998-12999.

Research output: Contribution to journalArticle

Niu, Wei ; Molefe, Mapitso N. ; Frost, J. W. / Microbial Synthesis of the Energetic Material Precursor 1,2,4-Butanetriol. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 43. pp. 12998-12999.
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abstract = "The lack of a route to precursor 1,2,4-butanetriol that is amenable to large-scale synthesis has impeded substitution of 1,2,4-butanetriol trinitrate for nitroglycerin. To identify an alternative to the current commercial synthesis of racemic D,L-1,2,4-butanetriol involving NaBH4 reduction of esterified D,L-malic acid, microbial syntheses of D- and L-1,2,4-butanetriol have been established. These microbial syntheses rely on the creation of biosynthetic pathways that do not exist in nature. Oxidation of D-xylose by Pseudomonas fragi provides D-xylonic acid in 70{\%} yield. Escherichia coli DH5α/pWN6.186A then catalyzes the conversion of D-xylonic acid into D-1,2,4-butanetriol in 25{\%} yield. P. fragi is also used to oxidize L-arabinose to a mixture of L-arabino-1,4-lactone and L-arabinonic acid in 54{\%} overall yield. After hydrolysis of the lactone, L-arabinonic acid is converted to L-1,2,4-butanetriol in 35{\%} yield using E. coli BL21(DE3)/pWN6.222A. As a catalytic route to 1,2,4-butanetriol, microbial synthesis avoids the high H2 pressures and elevated temperatures required by catalytic hydrogenation of malic acid.",
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