Found 21 structures.
Displayed structures from 1 to 15
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1. Compound ID: 19811
|
/Variants 0/-+
|
b-D-Glcp6(%)Ac-(1-2)-a-D-Glcp6(%)Ac
/Variants 0/ is:
R-17HOSte-(17-1)-
OR (exclusively)
R-17HOOle-(17-1)-
OR (exclusively)
R-17HOLin-(17-1)- |
Show graphically |
Structure type: oligomer
; 626-707 [M+H]+
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7827
Shao L, Song X, Ma X, Li H, Qu Y "Bioactivities of sophorolipid with different structures against human esophageal cancer cells" -
The Journal of Surgical Research 173(2) (2012) 286-291
Sophorolipids (SLs) obtained from yeast broth are mixtures of many sophorolipid molecules with different structures, and have attracted more attention since they were found to have good antimicrobial, anticancer, anti-inflammatory, and anti-HIV activities. We investigated the effects of sophorolipid molecules with different structures on human esophageal cancer cells in the present work. Ten sophorolipid (SL) molecules were separated and purified from the sophorolipids mixture using preparative HPLC, and their structures were identified by MS analyses. The effects of sophorolipid molecules with different structures on two human esophageal cancer cell lines, KYSE 109 and KYSE 450, were investigated by MTT assay. The structures of the 10 sophorolipid molecules differ in acetylation degree of sophorose, unsaturation degree of hydroxyl fatty acid, and lactonization or ring opening. The results demonstrated that the inhibition of diacetylated lactonic sophorolipid on two esophageal cancer cells (total inhibition at 30 μg/mL concentration) was stronger than that of monoacetylated lactonic sophorolipid (totally inhibition at 60 μg/mL concentration). Difference of unsaturation degree of hydroxyl fatty acid in SL molecules also had obvious influence on their cytotoxicity to esophageal cancer cells. The sophorolipid with one double bond in fatty acid part had the strongest cytotoxic effect on two esophageal cancer cells (total inhibition at 30 μg/mL concentration). Acidic sophorolipid showed hardly any anticancer activity against esophageal cancer cells. In this study, the relationship of anticancer activities of natural sophorolipid molecules and the differences in their structures was revealed, which probably further reveals the mechanism of SL bioactivities and will be helpful in the modification of SL structures to obtain more novel SLs with excellent bioactivities.
acetylation, sophorolipid, esophageal cancer, unsaturation degree, lactonization
NCBI PubMed ID: 21035135Publication DOI: 10.1016/j.jss.2010.09.013Journal NLM ID: 0376340Publisher: New York, NY: Academic Press
Correspondence: Song X
; Qu Y
Institutions: National Glycoengineering Research Center, Shandong University, Jinan, China, State Key Laboratory of Microbial Technology, Shandong University, Jinan, China
Methods: biological assays, MS, HPLC, UV, extraction, cell growth, evaporation, MTT
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2. Compound ID: 19812
| Cyclic
-2)-a-D-Glcp6(%)Ac-(1-17)-/Variants 0/-b-D-Glcp6(%)Ac-(1-
/Variants 0/ is:
R-17HOSte-(1-4)-
OR (exclusively)
R-17HOOle-(1-4)-
OR (exclusively)
R-17HOLin-(1-4)- |
Show graphically |
Structure type: cyclic polymer repeating unit
; 647-691 [M+H]+; n=1
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7827
Shao L, Song X, Ma X, Li H, Qu Y "Bioactivities of sophorolipid with different structures against human esophageal cancer cells" -
The Journal of Surgical Research 173(2) (2012) 286-291
Sophorolipids (SLs) obtained from yeast broth are mixtures of many sophorolipid molecules with different structures, and have attracted more attention since they were found to have good antimicrobial, anticancer, anti-inflammatory, and anti-HIV activities. We investigated the effects of sophorolipid molecules with different structures on human esophageal cancer cells in the present work. Ten sophorolipid (SL) molecules were separated and purified from the sophorolipids mixture using preparative HPLC, and their structures were identified by MS analyses. The effects of sophorolipid molecules with different structures on two human esophageal cancer cell lines, KYSE 109 and KYSE 450, were investigated by MTT assay. The structures of the 10 sophorolipid molecules differ in acetylation degree of sophorose, unsaturation degree of hydroxyl fatty acid, and lactonization or ring opening. The results demonstrated that the inhibition of diacetylated lactonic sophorolipid on two esophageal cancer cells (total inhibition at 30 μg/mL concentration) was stronger than that of monoacetylated lactonic sophorolipid (totally inhibition at 60 μg/mL concentration). Difference of unsaturation degree of hydroxyl fatty acid in SL molecules also had obvious influence on their cytotoxicity to esophageal cancer cells. The sophorolipid with one double bond in fatty acid part had the strongest cytotoxic effect on two esophageal cancer cells (total inhibition at 30 μg/mL concentration). Acidic sophorolipid showed hardly any anticancer activity against esophageal cancer cells. In this study, the relationship of anticancer activities of natural sophorolipid molecules and the differences in their structures was revealed, which probably further reveals the mechanism of SL bioactivities and will be helpful in the modification of SL structures to obtain more novel SLs with excellent bioactivities.
acetylation, sophorolipid, esophageal cancer, unsaturation degree, lactonization
NCBI PubMed ID: 21035135Publication DOI: 10.1016/j.jss.2010.09.013Journal NLM ID: 0376340Publisher: New York, NY: Academic Press
Correspondence: Song X
; Qu Y
Institutions: National Glycoengineering Research Center, Shandong University, Jinan, China, State Key Laboratory of Microbial Technology, Shandong University, Jinan, China
Methods: biological assays, MS, HPLC, UV, extraction, cell growth, evaporation, MTT
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3. Compound ID: 21346
| Cyclic
-4)-b-D-Glcp6(%)Ac-(1-2)-b-D-Glcp6(%)Ac-(1-17)-R-17HOOle-(1- |
Show graphically |
Structure type: cyclic polymer repeating unit
; n=1
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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4. Compound ID: 21347
Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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5. Compound ID: 21351
|
/Variants 0/-+
|
b-D-Glcp6(%)Ac-(1-2)-b-D-Glcp6(%)Ac-(1-17)-R-17HOOle
/Variants 0/ is:
Me-1)-
OR (exclusively)
Et-1)-
OR (exclusively)
Bu-1)- |
Show graphically |
Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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6. Compound ID: 21352
| Cyclic
?%Subst-(1-6)-+
|
-6)-b-D-Glcp-(1-2)-b-D-Glcp-(1-17)-R-17HOOle-(1-
Subst = acrylic acid = SMILES C=C{1}C(=O)O |
Show graphically |
Structure type: cyclic polymer repeating unit
; n=1
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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7. Compound ID: 21354
Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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8. Compound ID: 21355
|
/Variants 0/-b-D-Glcp-(1-2)-b-D-Glcp-(1-17)-R-17HOOle-(1-1)-Et
/Variants 0/ is:
Subst-(1-6)-
OR (exclusively)
Ac-6)-
Subst = metacrylic acid = SMILES C=C(C){1}C(=O)O |
Show graphically |
Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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9. Compound ID: 21358
|
/Variants 0/-+
|
b-D-Glcp-(1-2)-b-D-Glcp-(1-17)-R-17HOOle
/Variants 0/ is:
Subst-(1-1)-
OR (exclusively)
Subst3-(1-1)-
OR (exclusively)
Subst2-(1-1)-
OR (exclusively)
Subst1-(1-1)-
OR (exclusively)
Subst1-6Me-(1-1)-
Subst = 2-phenylethanamine = SMILES N{1}CCc1ccccc1;
Subst1 = tyramine = SMILES N{1}CCc1cc{6}c(O)cc1;
Subst2 = 2-(p-tolyl)ethylamine = SMILES Cc1ccc(C{1}CN)cc1;
Subst3 = 2-(4-fluorophenyl)ethanamine = SMILES N{1}CCc1ccc(F)cc1 |
Show graphically |
Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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10. Compound ID: 21359
|
/Variants 0/-+
|
/Variants 1/-b-D-Glcp-(1-2)-b-D-Glcp-(1-17)-R-17HOOle-(1-1)-Subst1
/Variants 0/ is:
?%Subst-(1-6)-
OR (exclusively)
?%Ac-6)-
/Variants 1/ is:
?%Subst-(1-6)-
OR (exclusively)
?%Ac-6)-
Subst = metacrylic acid = SMILES C=C(C){1}C(=O)O;
Subst1 = tyramine = SMILES N{1}CCc1cc{6}c(O)cc1 |
Show graphically |
Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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11. Compound ID: 21360
| Cyclic
/Variants 0/-+
|
-4)-b-D-Glcp6Ac-(1-2)-b-D-Glcp-(1-17)-R-17HOOle-(1-
/Variants 0/ is:
But-(1-6)-
OR (exclusively)
Subst-(1-6)-
OR (exclusively)
Subst1-(1-15)-Subst2-(1-6)-
Subst = metacrylic acid = SMILES C=C(C){1}C(=O)O;
Subst1 = TBDPS = SMILES CC(C)({1}[Si](C1=CC=CC=C1)(C2=CC=CC=C2)O)C;
Subst2 = 15-hydroxypentadecanoic acid = SMILES O={1}C(O)CCCCCCCCCCCCC{15}CO |
Show graphically |
Structure type: cyclic polymer repeating unit
; n=1
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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12. Compound ID: 21361
| Cyclic
-4)-b-D-Glcp2Pp3Pp6Ac-(1-2)-b-D-Glcp3Pp4Pp6(%)Ac-(1-17)-R-17HOOle-(1- |
Show graphically |
Structure type: cyclic polymer repeating unit
; n=1
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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13. Compound ID: 21362
| Cyclic
-4)-b-D-Glcp2Ac3Ac6Ac-(1-2)-b-D-Glcp3Ac4Ac6(%)Ac-(1-17)-R-17HOOle-(1- |
Show graphically |
Structure type: cyclic polymer repeating unit
; n=1
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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14. Compound ID: 21363
|
/Variants 0/-+
|
b-D-Glcp2Ac3Ac4Ac6Ac-(1-2)-b-D-Glcp3Ac4Ac6Ac-(1-17)-R-17HOOle
/Variants 0/ is:
?%Subst-(1-1)-
OR (exclusively)
?%Me-1)-
OR (exclusively)
?%Bu-1)-
Subst = isobutanol = SMILES CC(C){1}CO |
Show graphically |
Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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15. Compound ID: 21364
|
/Variants 0/-+
|
b-D-Glcp2Pp3Pp4Pp6Pp-(1-2)-b-D-Glcp3Pp4Pp6Pp-(1-17)-R-17HOOle
/Variants 0/ is:
?%Subst-(1-1)-
OR (exclusively)
?%Me-1)-
OR (exclusively)
?%Bu-1)-
Subst = isobutanol = SMILES CC(C){1}CO |
Show graphically |
Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8603
Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" -
Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.
enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering
Publication DOI: 10.1016/B978-0-12-813167-1.00014-1Publisher: N.J.: Academic Press and AOCS Press
Editors: Bornscheuer UT
Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
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