Sophorolipid-1-acid
Sophorolipids (SLs) are a family of fungal biosurfactants that have been commercialized as biodegradable detergents in ecological cleaning solutions. They naturally exist in two forms, a closed lactone and an open acidic form. Each form has distinct properties; acidic SLs have better foaming properties, while lactonic SLs are better in surface tension reduction and have antimicrobial activity. Lactone esterase, catalyzing the final conversion of the open bolaform SLs to the closed lactonic form, provides a biotechnological opportunity to engineer and regulate the production of SLs in S.bombicola, which naturally produces a mixture of acidic and lactonic SLs. Produced by non-pathogenic yeasts using sugars and vegetable oils
General
Type : Glycoside, Natural, Oleate
Chemical_Nomenclature : 17-[(6-O-acetyl-beta-D-glucosyl-(1->2)-6-O-acetyl-beta-D-glucosyl)oxy]-oleate-6-O-acetyl-beta-D-glucosyl-(1->2)-6-O-acetyl-beta-D-glucoside
Canonical SMILES : CC(=O)OC[C@H]1O[C@@H](O[C@H]2[C@H](OC(C)CCCCCC\/C=CCCCCCCCC(=O)O[C@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)O[C@H](COC(C)=O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
InChI : InChI=1S\/C50H82O27\/c1-25(70-49-45(41(62)37(58)32(73-49)23-68-28(4)53)76-47-43(64)39(60)35(56)30(71-47)21-66-26(2)51)19-17-15-13-11-9-7-6-8-10-12-14-16-18-20-34(55)75-50-46(42(63)38(59)33(74-50)24-69-29(5)54)77-48-44(65)40(61)36(57)31(72-48)22-67-27(3)52\/h6-7,25,30-33,35-50,56-65H,8-24H2,1-5H3\/b7-6-\/t25?,30-,31-,32-,33-,35-,36-,37-,38-,39+,40+,41+,42+,43-,44-,45-,46-,47+,48+,49-,50-\/m1\/s1
InChIKey : XHCWWGGCMHXKCH-IMJVEFGTSA-N
Other name(s) : CHEBI:235373
Target
Structures : No structure
Families : Fungal-Bact_LIP
References (8)
| Title : Transcriptomics-Driven Identification and Engineering of a Novel Lactone Esterase (SrLE) for Efficient Sophorolipid Lactonization in the Yeast Starmerella riodocensis - Sapsirisuk_2026_Biotechnol.Bioeng__ |
| Author(s) : Sapsirisuk S , Lee J , Bogaert I , Soontorngun N |
| Ref : Biotechnol Bioeng , : , 2026 |
| Abstract : |
| PubMedSearch : Sapsirisuk_2026_Biotechnol.Bioeng__ |
| PubMedID: 42788968 |
| Gene_locus related to this paper: 9asco-SrLE |
| Title : Bubbling insights: unveiling the true sophorolipid biosynthetic pathway by Starmerella bombicola - Roelants_2024_Biotechnol.Biofuels.Bioprod_17_113 |
| Author(s) : Roelants S , Bovijn S , Bytyqi E , de Fooz N , Luyten G , Castelein M , Van de Craen T , Diao Z , Maes K , Delmulle T , De Mol M , De Maeseneire SL , Devreese B , Soetaert WK |
| Ref : Biotechnol Biofuels Bioprod , 17 :113 , 2024 |
| Abstract : |
| PubMedSearch : Roelants_2024_Biotechnol.Biofuels.Bioprod_17_113 |
| PubMedID: 39143561 |
| Gene_locus related to this paper: stabo-sble |
| Title : Revision of the sophorolipid biosynthetic pathway in Starmerella bombicola based on new insights in the substrate profile of its lactone esterase - Diao_2024_Biotechnol.Biofuels.Bioprod_17_89 |
| Author(s) : Diao Z , Roelants S , Luyten G , Goeman J , Vandenberghe I , Van Driessche G , De Maeseneire SL , Soetaert WK , Devreese B |
| Ref : Biotechnol Biofuels Bioprod , 17 :89 , 2024 |
| Abstract : |
| PubMedSearch : Diao_2024_Biotechnol.Biofuels.Bioprod_17_89 |
| PubMedID: 38937850 |
| Gene_locus related to this paper: stabo-sble |
| Title : Optimized expression of the Starmerella bombicola lactone esterase in Pichia pastoris through temperature adaptation, codon-optimization and co-expression with HAC1 - De Waele_2018_Protein.Expr.Purif_143_62 |
| Author(s) : De Waele S , Vandenberghe I , Laukens B , Planckaert S , Verweire S , Van Bogaert INA , Soetaert W , Devreese B , Ciesielska K |
| Ref : Protein Expr Purif , 143 :62 , 2018 |
| Abstract : |
| PubMedSearch : De Waele_2018_Protein.Expr.Purif_143_62 |
| PubMedID: 29108944 |
| Gene_locus related to this paper: stabo-sble |
| Title : Synthesis of bolaform biosurfactants by an engineered Starmerella bombicola yeast - Van Bogaert_2016_Biotechnol.Bioeng_113_2644 |
| Author(s) : Van Bogaert IN , Buyst D , Martins JC , Roelants SL , Soetaert WK |
| Ref : Biotechnol Bioeng , 113 :2644 , 2016 |
| Abstract : |
| PubMedSearch : Van Bogaert_2016_Biotechnol.Bioeng_113_2644 |
| PubMedID: 27317616 |
| Gene_locus related to this paper: stabo-sble |
| Title : Characterization of a novel enzyme-Starmerella bombicola lactone esterase (SBLE)-responsible for sophorolipid lactonization - Ciesielska_2016_Appl.Microbiol.Biotechnol_100_9529 |
| Author(s) : Ciesielska K , Roelants SL , Van Bogaert IN , De Waele S , Vandenberghe I , Groeneboer S , Soetaert W , Devreese B |
| Ref : Applied Microbiology & Biotechnology , 100 :9529 , 2016 |
| Abstract : |
| PubMedSearch : Ciesielska_2016_Appl.Microbiol.Biotechnol_100_9529 |
| PubMedID: 27251547 |
| Gene_locus related to this paper: stabo-sble |
| Title : Towards the industrialization of new biosurfactants: Biotechnological opportunities for the lactone esterase gene from Starmerella bombicola - Roelants_2016_Biotechnol.Bioeng_113_550 |
| Author(s) : Roelants SL , Ciesielska K , De Maeseneire SL , Moens H , Everaert B , Verweire S , Denon Q , Vanlerberghe B , Van Bogaert IN , Van der Meeren P , Devreese B , Soetaert W |
| Ref : Biotechnol Bioeng , 113 :550 , 2016 |
| Abstract : |
| PubMedSearch : Roelants_2016_Biotechnol.Bioeng_113_550 |
| PubMedID: 26301720 |
| Gene_locus related to this paper: stabo-sble |
| Title : Exoproteome analysis of Starmerella bombicola results in the discovery of an esterase required for lactonization of sophorolipids - Ciesielska_2014_J.Proteomics_98_159 |
| Author(s) : Ciesielska K , Van Bogaert IN , Chevineau S , Li B , Groeneboer S , Soetaert W , Van de Peer Y , Devreese B |
| Ref : J Proteomics , 98 :159 , 2014 |
| Abstract : |
| PubMedSearch : Ciesielska_2014_J.Proteomics_98_159 |
| PubMedID: 24418522 |
| Gene_locus related to this paper: stabo-sble |