FUNCTIONALISED POLSULPHIDE SYNTHESIS METHOD

1 . A process for synthesizing at least one functionalized organic polysulfide of formula (I):

R 2 —X—(NR 1 R 7 )C*H—(CH 2 ) n —S a —(CH 2 ) n —C*H(NR 1 R 7 )—X—R 2   (I)

wherein:

R 1 and R 7 are a hydrogen or an aromatic or nonaromatic, or a linear or cyclic, saturated or unsaturated, branched or unbranched, hydrocarbon chain of 1 to 20 carbon atoms, which can comprise heteroatoms, wherein R 1 and R 7 are identical or different;

X is —C(═O)— or —CH 2 — or —CN;

R 2 is (i) nonexistent when X represents —CN, (ii) a hydrogen, (iii) —OR 3 , wherein R 3 is a hydrogen or an aromatic or nonaromatic, or a linear or cyclic, saturated or unsaturated, branched or unbranched, hydrocarbon chain of 1 to 20 carbon atoms, which can comprise heteroatoms, or (iv) —NR 4 R 5 , wherein R 4 and R 5 are a hydrogen or an aromatic or nonaromatic, or a linear or cyclic, saturated or unsaturated, branched or unbranched, hydrocarbon chain of 1 to 20 carbon atoms, which can comprise heteroatoms, and wherein R 4 and R 5 are identical or different;

n is 1 or 2;

a is an integer or decimal number between 2 and 10; and

C* represents an asymmetric carbon;

the process comprising:

(a) providing at least one compound of formula (II):

G−(CH 2 ) n —C*H(NR 1 R 7 )—X—R 2   (II)

wherein:

n, R 1 , R 2 , R 7 , X and C* are as defined above,

G is (i) R 6 —C(═O)—O—, (ii) (R 8 O)(R 9 O)—P(═O)—O—, or (iii) R 8 O—SO 2 —O—;

R 6 is a hydrogen or an aromatic or nonaromatic, or a linear or cyclic, saturated or unsaturated, branched or unbranched, hydrocarbon chain of 1 to 20 carbon atoms, which can comprise heteroatoms;

R 8 and R 9 are H, an alkali metal, an alkaline earth metal or an ammonium, wherein R 8 and R 9 , are identical or different;

(b) providing at least one inorganic polysulfide;

(c) reacting the at least one compound of formula (II) with the at least one inorganic polysulfide in the presence of at least one enzyme chosen from sulfhydrylase;

(d) obtaining at least one functionalized organic polysulfide of formula (I);

(e) separating and isolating the at least one functionalized organic polysulfide of formula (I) and;

(f) optionally, further functionalizing the functionalized organic polysulfide of formula (I) obtained in stage (d) or (e);

wherein stages (a) and (b) are carried out simultaneously or sequentially.

2 . The process as claimed in claim 1 , wherein the functionalized organic polysulfide of formula (I) is enantiomerically pure.

3 . The process as claimed in claim 1 , wherein the functionalized organic polysulfide of formula (I) is chosen from dicysteine polysulfide and dihomocysteine polysulfide.

4 . The process as claimed in claim 1 , wherein the compound of formula (II) is chosen from I-serine derivatives and I-homoserine derivatives.

5 . The process as claimed in claim 4 , wherein the I-serine derivative is chosen from O-phospho-L-serine, O-succinyl-L-serine, O-acetyl-L-serine, O-acetoacetyl-L-serine, O-propio-L-serine, O-coumaroyl-L-serine, O-malonyl-L-serine, O-hydroxymethylglutaryl-L-serine, O-pimelyl-L-serine and O-sulfo-L-serine.

6 . The process as claimed in claim 4 , wherein the I-homoserine derivative is chosen from O-phospho-L-homoserine, O-succinyl-L-homoserine, O-acetyl-L-homoserine, O-acetoacetyl-L-homoserine, propio-L-homoserine, O-coumaroyl-L-homoserine, O-malonyl-L-homoserine, O-hydroxymethylglutaryl-L-homoserine, O-pimelyl-L-homoserine and O-sulfo-L-homoserine.

7 . The process as claimed in claim 4 , wherein the sulfhydrylase is chosen from sulfhydrylases associated with the L-serine derivatives and sulfhydrylases associated with the L-homoserine derivatives.

8 . The process as claimed in claim 7 , wherein the sulfhydrylase associated with the L-serine derivative is chosen from O-phospho-L-serine sulfhydrylase, O-succinyl-L-serine sulfhydrylase, O-acetyl-L-serine sulfhydrylase, acetoacetyl-L-serine sulfhydrylase, O-propio-L-serine sulfhydrylase, O-coumaroyl-L-serine sulfhydrylase, O-malonyl-L-serine sulfhydrylase, O-hydroxymethylglutaryl-L-serine sulfhydrylase, O-pimelyl-L-serine sulfhydrylase and O-sulfo-L-serine.

9 . The process as claimed in claim 7 , wherein the sulfhydrylase associated with the L-homoserine derivative is chosen from O-phospho-L-homoserine sulfhydrylase, O-succinyl-L-homoserine sulfhydrylase, O-acetyl-L-homoserine sulfhydrylase, O-acetoacetyl-L-homoserine sulfhydrylase, O-propio-L-homoserine sulfhydrylase, O-coumaroyl-L-homoserine sulfhydrylase, O-malonyl-L-homoserine sulfhydrylase, O-hydroxymethylglutaryl-L-homoserine sulfhydrylase, O-pimelyl-L-homoserine sulfhydrylase and O-sulfo-L-homoserine sulfhydrylase.

10 . The process as claimed in claim 1 , wherein the inorganic polysulfide is chosen from alkali metal, alkaline earth metal and ammonium polysulfides.

11 . A functionalized organic polysulfide of formula (I) prepared according to the process described in claim 1 .

12 . Dicysteine or dihomocysteine polysulfide prepared according to the process described in claim 1 .

13 . A process for lubrication, vulcanization, sulfidation of catalysts or preparation of medicaments, comprising using a functionalized organic polysulfide as claimed in claim 11 .

14 . The process as claimed in claim 1 , wherein the sulfhydrylase is a sulfhydrylase associated with the compound of formula (II).

15 . The process as claimed in claim 4 , wherein the L-serine derivative is selected from the group consisting of O-phospho-L-serine, O-succinyl-L-serine, O-acetyl-L-serine and O-sulfo-L-serine.

16 . The process as claimed in claim 4 , wherein the L-homoserine derivative is selected from the group consisting of O-succinyl-L-homoserine, O-acetyl-L-homoserine, O-phospho-homoserine and O-sulfo-L-homoserine.

17 . The process as claimed in claim 7 , wherein the sulfhydrylase associated with the L-serine derivative is selected from the group consisting of O-phospho-L-serine, O-succinyl-L-serine sulfhydrylase, O-acetyl-L-serine sulfhydrylase and O-sulfo-L-serine.

18 . The process as claimed in claim 7 , wherein the sulfhydrylase associated with the L-homoserine derivative is selected from the group consisting of O-phospho-L-homoserine sulfhydrylase, O-succinyl-L-homoserine sulfhydrylase, O-acetyl-L-homoserine sulfhydrylase and O-sulfo-L-homoserine sulfhydrylase.

19 . The process as claimed in claim 1 , wherein the inorganic polysulfide is selected from the group consisting of sodium polysulfide, potassium polysulfide, calcium polysulfide and ammonium polysulfide.