Synthesis of 1,2,4-butanetriol enantiomers from carbohydrates
AssigneeBoard of Trustees of Michigan State University
InventorJohn Frost
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Abstract
A bioengineered synthesis scheme for the production of L-1,2,4-butanetriol, D-1,2,4-butanetriol and racemic mixtures thereof from a carbon source is provided. Methods of producing L-1,2,4-butanetriol, D-1,2,4-butanetriol and racemic mixtures thereof are also provided. Methods are also provided for converting D-1,2,4-butanetriol and L-1,2,4,-butanetriol to D,L-1,2,4-butanetriol trinitrate.
Claims60
A process for making 1,2,4-butanetriol, comprising the steps of
- (a) providing at least one of D-xylonic acid or L-arabinonic acid;
- (b) converting acid of step (a) to 3-deoxy-glycero-pentulosonic acid;
- (c) converting 3-deoxy-glycero-pentulosonic acid resulting from step (b) to 3,4-dihydroxybutanal;
- and
- (d) converting 3,4-dihydroxybutanal resulting from step (c) to 1,2,4-butanetriol.
Biosynthetic 1,2,4-butanetriol.
A process for the production of 1,2,4-butanetriol trinitrate from 1,2,4-butanetriol, comprising the steps of:
- (a) providing a nitrating agent,
- (b) providing, as the 1,2,4-butanetriol, any one of D-1,2,4-butanetriol, L-1,2,4-butanetriol, or a combination thereof,
- (c) contacting said 1,2,4-butanetriol with said nitrating agent under conditions in which the 1,2,4-butanetriol and the nitrating agent can react to form 1,2,4-butanetriol trinitrate, thereby respectively producing D-1,2,4-butanetriol trinitrate, L-1,2,4-butanetriol trinitrate, or a combination thereof,
- wherein said 1,2,4-butanetriol comprises biosynthetic 1,2,4-butanetriol.
A process for making 3,4-dihydroxybutanal, comprising culturing a microbe expressing 2-ketoacid decarboxylase in the presence of 3-deoxy-glycero-pentulosonic acid.
A non-naturally occurring enzyme system including (1) at least one D-xylonate dehydratase, at least one 2-ketoacid decarboxylase, and at least one alcohol dehydrogenase or carbonyl reductase, wherein said enzyme system is capable of catalyzing the conversion of D-xylonic acid to D-1,2,4-butanetriol;
- or including (2) at least one L-arabinonate dehydratase, at least one 2-ketoacid decarboxylase, and at least one alcohol dehydrogenase or carbonyl reductase, wherein said enzyme system is capable of catalyzing the conversion of L-arabinonic acid to L-1,2,4-butanetriol.
Dependencies are inferred from the claim text.