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US 10,648,007 B2Granted
Method for producing mercaptans by hydrogen-assisted disulfide enzyme hydrogenolysis
AssigneeArkema France
InventorsGeorges Fremy, Arnaud Masselin, Hugo Brasselet
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Abstract
Provided is an enzymatic process for the preparation of a mercaptan of formula R—SH from disulfides utilizing hydrogen.
Claims16
A process for the preparation of a mercaptan of formula R—SH, comprising:
- (a) preparing a mixture, comprising:
- (1) a disulfide of formula R—S—S—R′,
- wherein R and R′, independently, represent a linear, branched or cyclic hydrocarbon-based radical comprising from 1 to 20 carbon atoms, wherein the hydrocarbon-based radical is saturated or contains one or more unsaturations in the form of double or triple bond(s), or R and R′ form together, with the sulfur atoms bearing them, a cyclic group comprising from 4 to 22 atoms,
- (2) a catalytic amount of an amino acid bearing a thiol group or of a thiol-group-containing peptide, wherein the amino acid bearing a thiol group or the thiol-group-containing peptide may optionally be in the form of the corresponding disulfide,
- (3) a catalytic amount of an enzyme catalyzing the reduction of a disulfide bridge created between two equivalents of the amino acid bearing a thiol group or of the thiol-group-containing peptide,
- (4) a catalytic amount of an enzyme catalyzing the reduction of hydrogen, and
- (5) a catalytic amount of a cofactor common to the enzyme catalyzing the reduction of a disulfide bridge created between two equivalents of the amino acid bearing a thiol group or of the thiol-group-containing peptide and the enzyme catalyzing the reduction of hydrogen,
- (b) adding hydrogen with a catalytic amount of a hydrogen dehydrogenase enzyme,
- (c) carrying out the enzymatic reaction,
- (d) recovering the mercaptan of formula R—SH and the mercaptan of formula R′—SH,
- (e) optionally, separating and, optionally, purifying the mercaptan of formula R—SH and/or of the mercaptan of formula R′—SH.
8 more elements
A mixture, comprising:
- (1) a disulfide of formula R—S—S—R′,
- wherein R and R′, independently, represent a linear, branched or cyclic hydrocarbon-based radical comprising from 1 to 20 carbon atoms, wherein the hydrocarbon-based radical is saturated or contains one or more unsaturations in the form of double or triple bond(s), or R and R′ form together, with the sulfur atoms bearing them, a cyclic group comprising from 4 to 22 atoms,
- (2) a catalytic amount of amino acid bearing a thiol group or of a thiol-group-containing peptide, wherein the amino acid bearing a thiol group or the thiol-group-containing peptide may optionally be in the form of the corresponding disulfide,
- (3) a catalytic amount of an enzyme catalyzing the reduction of a disulfide bridge created between two equivalents of the amino acid bearing a thiol group or of the thiol-group-containing peptide,
- (4) optionally, a catalytic amount of an enzyme catalyzing the reduction of hydrogen,
- (5) a catalytic amount of a cofactor common to the enzyme catalyzing the reduction of a disulfide bridge created between two equivalents of the amino acid bearing a thiol group or of the thiol-group-containing peptide and the enzyme catalyzing the reduction of hydrogen, and
- (6) optionally, hydrogen.
4 more elements
Dependencies are inferred from the claim text.