Method for producing mercaptans by disulfide enzyme hydrogenolysis

Abstract

Provided is an enzymatic process for preparing mercaptans from disulfides.

1 .- 13 . (canceled) 
     
     
         14 . A mixture, comprising:
 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, and with the sulfur atoms bearing them, a cyclic group comprising from 4 to 22 atoms, 
   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,   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 the thiol-group-containing peptide,   optionally, a catalytic amount of an enzyme catalyzing the dehydrogenation of an organic reducing compound, and   a catalytic amount of a cofactor common to the two enzymes catalyzing the reduction and the dehydrogenation.   
     
     
         15 . The mixture of  claim 14 , comprising:
 a disulfide of formula R—S—S—R′,   a catalytic amount of the amino acid bearing a thiol group or the thiol-group-containing peptide,   a catalytic amount of a reductase enzyme corresponding to the amino acid bearing a thiol group or the thiol-group-containing peptide, and   a catalytic amount of NADPH.   
     
     
         16 . The mixture of  claim 14 , wherein the disulfide of formula R—S—S—R′ is dimethyl disulphide. 
     
     
         17 . The mixture of  claim 14 , wherein the amino acid bearing a thiol group or the peptide bearing a thiol group is chosen from cysteine, homocysteine, glutathione and thioredoxin. 
     
     
         18 . The mixture of  claim 14 , wherein the organic reducing compound is a hydrogen-donating organic reducing compound bearing a hydroxyl function, chosen from alcohols, polyols, sugars, etc. 
     
     
         19 . The mixture of  claim 14 , wherein the organic reducing compound is chosen from glucose, glucose 6-phosphate and isopropanol. 
     
     
         20 . The mixture of  claim 14 , wherein the organic reducing compound/disulfide molar ratio is between 0.01 and 100. 
     
     
         21 . The mixture of  claim 14 , wherein the organic reducing compound/disulfide molar ratio is between 0.5 and 5. 
     
     
         22 . The mixture of  claim 14 , wherein:
 the disulfide of formula R—S—S—R′ is dimethyl disulfide (DMDS),   the amino acid bearing a thiol group or the peptide bearing a thiol group is chosen from cysteine, homocysteine, glutathione and thioredoxin,   the organic reducing compound is a hydrogen-donating organic reducing compound bearing a hydroxyl function and is chosen from alcohols, polyols, and sugars, and   the cofactor is a flavinic cofactor or a nicotinic cofactor.   
     
     
         23 . The mixture of  claim 14 , wherein:
 the disulfide of formula R—S—S—R′ is dimethyl disulfide (DMDS),   the amino acid bearing a thiol group or the peptide bearing a thiol group is glutathione,   the organic reducing compound is glucose, and   the cofactor is NADPH.