Glycolipopeptide biosurfactants

Patent metadata

Field	Value
Publication number	US-2019127411-A1
Application number	US-201716090888-A
Country	US
Kind code	A1
Filing date	Apr 6, 2017
Priority date	Apr 6, 2016
Publication date	May 2, 2019
Grant date	—

Abstract

Surfactants based on a newly discovered class of compounds include a hydrophobic lipid oligomer covalently linked to a peptide or peptide-like chain and a carbohydrate moiety, and a serine-leucinol dipeptide linked to the lipid oligomer. Such surfactants can be used to create an oil-in-water or water-in-oil emulsion by mixing together a polar component; a non-polar component; and the surfactant. Biosurfactants of the newly discovered class can be made by isolating and culturing a microorganism which produces the biosurfactant, and then isolating the biosurfactant from the culture. A microorganism can be engineered to produce biosurfactant of this newly discovered class by expressing a set of heterologous genes involved in the biosynthesis of the biosurfactant in the microorganism.

First claim

1 . A purified biosurfactant comprising a hydrophobic lipid component comprising a carboxyl end and a hydroxyl end, wherein the lipid component is covalently linked to (i) a peptide or peptide-like chain at the carboxyl end of the lipid component and (ii) a carbohydrate moiety at the hydroxyl end of the lipid component via a glycosidic linkage.

2 . The purified biosurfactant according to claim 1 , wherein the peptide chain comprises in the range of between 2 and 10 amino acids.

3 . The purified biosurfactant according to claim 1 , wherein the lipid component comprises in the range of between 1 and 6 alkanoic acid moieties

4 . The purified biosurfactant according to claim 1 , wherein the lipid component comprises an acyle chain, and wherein the length of each said acyl chain is in the range of between C 4 to C 20 .

5 . The purified biosurfactant according to claim 1 , wherein the carbohydrate moiety may be selected from saccharides including glucose, fructose, galactose, mannose, ribose, or deoxy saccharide variants including deoxyribose, fucose, or rhamnose.

6 . The purified biosurfactant according to claim 1 , wherein the peptide or peptide-like chain comprises a serine-leucinol dipeptide.

7 . The purified biosurfactant according to claim 1 , wherein the lipid component comprises three 3-hydroxyalkanoic acid moieties.

8 . The purified biosurfactant of claim 4 , wherein the length of each acyl chain of the lipid component is C 10 .

9 . The purified biosurfactant according to claim 1 , wherein the carbohydrate moiety comprises a rhamnose moiety attached to the lipid component via a glycosidic linkage.

10 . The purified biosurfactant according to claim 9 , wherein the carbohydrate moiety comprises two rhamnose moieties.

11 . The purified biosurfactant according to claim 1 , wherein the lipid component comprises three β-hydroxyalkanoic acid moieties, the length of each acyl chain of the lipid component is C 10 , and the carbohydrate moiety comprises a rhamnose moiety attached to the lipid component via a glycosidic linkage.

12 . A purified biosurfactant comprising a peptide or peptide-like portion covalently bound to a lipid portion, wherein the biosurfactant comprises the structure:

wherein R 1a is selected from the group consisting of H, OH, OCH 3 , SH, S(CH 3 ), NH 2 , NH(CH 3 ), N(CH 3 ) 2 , and a peptide or peptide-like structure having the structure:

wherein R 1b , R 1c , and R 1d , are selected from the group consisting of H, OH, OCH 3 , SH, S(CH 3 ), NH 2 , NH(CH 3 ), and N(CH 3 ) 2 ;
R 2a , R 2b , R 2c , and R 2d are each independently an amino acid side chain;
X 1a , X 1b , X 1c , and X 1d are each independently selected from the group consisting of one oxygen atom and two hydrogen atoms;
X 2a , X 2b , X 2c , and X 2d are each independently selected from the group consisting of NH, N(CH 3 ), and O;
R 3a is selected from the group consisting of a carbohydrate portion, and a lipid selected from the group consisting of a monomer having the structure:

and an oligomer selected from the group consisting of:

wherein X 3a , X 3b , X 3c , and X 3d are each independently selected from the group consisting of NH, N(CH 3 ), and O;
R 3a , R 3b , R 3c , and R 3d comprises a carbohydrate portion comprising a monomer selected from the group consisting of:

wherein R 5a , R 6a , R 7a , and R 8a are each independently selected from the group consisting of a hydrogen atom, methyl, acetyl, and a carbohydrate;
and R 4a , R 4b , R 4c , and R 4d are each independently selected from the group consisting of a hydrogen atom, methyl, and a C 2 to C 19 saturated or unsaturated linear, branched-chain, cyclic, or aromatic hydrocarbon groups.

13 . The purified biosurfactant of claim 12 , wherein at least one of R 6a , R 7a , and R 8a comprises a carbohydrate comprising a monomer selected from the group consisting of:

wherein R 5b , R 6b , R 7b , and R 8b are each independently selected from the group consisting of a hydrogen atom, methyl, acetyl, and a carbohydrate.

14 . The purified biosurfactant of claim 12 , wherein the peptide or peptide-like portion comprises at least one proline or proline-like monomer having the structure:

wherein X 4 is selected from the group consisting of one oxygen atom and two hydrogen atoms.

15 . The purified biosurfactant of claim 14 , wherein the peptide or peptide-like portion comprises a single proline or proline-like monomer or a terminal proline or proline-like monomer having the structure:

wherein R 9 is selected from the group consisting of H, OH, OCH 3 , SH, S(CH 3 ), NH 2 , NH(CH 3 ), and N(CH 3 ) 2 ; and X 4 is selected from the group consisting of one oxygen atom and two hydrogen atoms.

16 . A purified biosurfactant, wherein the biosurfactant has the structure:

wherein R 5a , R 6a , R 7a , R 10 , and R 11 are each independently selected from the group consisting of a hydrogen atom and acetyl; and n 1 , n 2 , and n 3 are integers each independently selected from 1 to 7.

17 . The purified biosurfactant of claim 16 , wherein the biosurfactant has the structure:

wherein R 5a , R 5b , R 6b , R 7a , R 7b , R 10 , and R 11 are each independently selected from the group consisting of a hydrogen atom and acetyl; and n 1 , n 2 , and n 3 are integers each independently selected from 1 to 7.

18 . The purified biosurfactant of claim 16 , wherein the biosurfactant has the structure:

19 . The purified biosurfactant of claim 17 , wherein the biosurfactant has the structure:

20 . The purified biosurfactant of claim 17 , wherein the biosurfactant has the structure:

21 . A method of making the biosurfactant of claim 1 , the method comprising the steps of:
(a) isolating a microorganism which comprises the biosurfactant; (b) placing the microorganism in a culture under conditions that promote the synthesis of the biosurfactant; and (c) isolating the biosurfactant from the culture.

22 . The method according to claim 21 , wherein the microorganism belongs to the genus and species Variovorax paradoxus a

Assignees

• Croda Int Plc

Inventors

• Kerr Russell Greig
• Haltli Bradley Arnold
• Marchbank Douglas Hubert
• Berrué Fabrice

Classifications

• C12P19/44

  Preparation of O-glycosides, e.g. glucosides {(polysaccharides and not substituted disaccharides C12P19/04, C12P19/12)} · CPC title

• C12N15/52

  Genes encoding for enzymes or proenzymes · CPC title

• C07H15/04 Primary

  attached to an oxygen atom of the saccharide radical · CPC title

• C11D1/008

  Polymeric surface-active agents · CPC title

• C07H1/08

  from natural products · CPC title