Enzyme-catalyzed regioselective transesterification of peracylated sophorolipids

Carr, Jason A.; Bisht, Kirpal S.

doi:10.1016/s0040-4020(03)01213-4

Cited by 27 publications

(11 citation statements)

References 25 publications

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“…Due to the free carboxyl group, an unsaturated carbon chain and the presence of a carbohydrate head group, glucolipids are interesting intermediates for several kinds of biocatalytic or chemical conversion reactions. Since small structural variations can have a significant influence on biological activity or the physicochemical properties of a glycolipid, enzymatic or chemo‐enzymatic synthesis of sophorolipid derivatives has been the subject of some research papers (Bisht et al , 1999; Carr and Bisht, 2003; Rau et al , 2001) and patent applications (Gross and Shah, 2004, 2005). To date, glucolipids with a free carboxylic end are only produced by enzymatic conversion of acidic (open‐ring) sophorolipids, which are in their turn obtained after alkaline hydrolysis of the crude C. bombicola bioproduct (Rau et al , 1999; Saerens et al , 2009) or might be produced in acetylated form by a recently identified new sophorolipid producer (Imura et al , 2010).…”

Section: Resultsmentioning

confidence: 99%

Cloning and functional characterization of the UDP‐glucosyltransferase UgtB1 involved in sophorolipid production by Candida bombicola and creation of a glucolipid‐producing yeast strain

Saerens

Zhang

Saey

et al. 2011

Yeast

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Sophorolipids produced by the non-pathogenic yeast Candida bombicola ATCC 22214 are glycolipid biosurfactants applied commercially as biodegradable and eco-friendly detergents. Their low cell toxicity, excellent wetting capability and antimicrobial activity attract the attention of high-value markets, such as the cosmetic and pharmaceutical industries. Although sophorolipid production yields have been increased by the optimization of fermentation parameters and feed sources, the biosynthetic pathway and genetic mechanism behind sophorolipid production still remains unclear. Here we identify a UDP-glucosyltransferase gene, UGTB1, with a key function in this economically important pathway. The protein shows sequence and structural homology to several bacterial glycosyltransferases involved in macrolide antibiotic synthesis. Deletion of UGTB1 in C. bombicola did not affect cell growth and resulted in a yeast producing glucolipids, thereby opening the route for in vivo production of these glycolipid intermediates. Activity assays on cell lysates confirmed that the identified gene is responsible for the second glucosylation step during sophorolipid production and illustrated that sophorolipid production in C. bombicola involves the stepwise action of two independent glucosyltransferases. The complete UGTB1 sequence data have been submitted to the GenBank database (http://www.ncbi.nlm.nih.gov) under Accession No. HM440974.

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Section: Resultsmentioning

confidence: 99%

Cloning and functional characterization of the UDP‐glucosyltransferase UgtB1 involved in sophorolipid production by Candida bombicola and creation of a glucolipid‐producing yeast strain

Saerens

Zhang

Saey

et al. 2011

Yeast

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“…Only a few biological activities have been reported for microbial glycolipids such as the growth inhibition of human promyelozytic leukemia cells HL60 40, action on HIV, and the immobilization of sperms 41, operating as immune modulators for Parkinson's or Alzheimer's disease 42, showing good properties in the therapy of sepsis 43 and acting against human pancreas cancer cells 44. In the present study, two tests were chosen: the agar diffusion test and the test on anti‐tumor promoting activity.…”

Section: Discussionmentioning

confidence: 99%

Enzymatic production of modified 2‐dodecyl‐sophorosides (biosurfactants) and their characterization

Recke

Gerlitzki

Hausmann

et al. 2013

Euro J Lipid Sci & Tech

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Alkyl sophorosides, a special type of sophorolipids, can be produced using Candida bombicola cultures with glucose as main carbon source and 2-dodecanol as co-substrate. The dominating component, 2-dodecylsophoroside SL-E 2-12 , was purified via medium pressure liquid chromatography (MPLC) and used as substrate for further enzymatic modifications. Using b-glucuronidase in aqueous media the first modification gave a glycosidic cleavage of the acetyl glucose unit leading to 2-dodecyl-glucoside GL-A 2-12 . In a subsequent lipase-catalyzed acylation with sebacic acid in toluene this compound was functionalized regioselectively at the primary C-6 0 position of glucose. Similar lipase-catalyzed reactions in toluene, but now using SL-E 2-12 as acyl acceptor and unusual hydroxyl fatty acids -3-hydroxy decanoic acid and 17-hydroxy stearic acid -as acyl donors, resulted in mono-and diacylations of primary hydroxyl positions of the sophorose unit (C-6 0 and C-6 00 ) as shown by NMR and MS studies. In physicochemical characterization experiments the new glycoconjugates lowered the surface tension of water from 72 to 27-32 mN/m. Moreover it was observed that the new products inhibit the growth of particular Gram-positive bacteria. Additionally they indicate potential for anti-tumor promoting activity.Practical applications: According to literature data 2-alkyl-sophorosides can be produced using Candida bombicola cultures with yields of more than 20 g/L. Based on this starting material, 2-dodecyl-sophoroside, several regioselective enzymatic modifications were performed. Initially, b-glucuronidase catalysis in aqueous buffer solution gave 2-dodecyl-glucoside which was then successfully acylated at the C-6 position of glucose by lipase catalysis using a common dicarboxylic acid, sebacic acid. The resulting free carboxylic function of the acidic derivative opens up the possibility of achieving additional chemo-enzymatic reactions at this position for conversion, for instance, into polyesters. In addition lipase catalysis in organic solvents of 2-dodecyl-sophoroside allows acylation with unusual hydroxyl fatty acids of microbial origin. Physicochemical studies showed that these new glycoconjugates may be of interest for the cosmetic industry due to moisture conservation of the skin. For practical applications the conditions of the above biocatalytic reactions have been improved and scaled up.

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“…In [18], sophorolipids from Candida bombicola have received particular attention and have been used to produce derivatives. For instance, several alkyl esters and amides have been synthesized chemically or enzymatically using lipases [19][20][21]. Another interesting paper reports the lipase-catalyzed synthesis of a new type of sophorolipid that has been obtained by esterifying the primary alcohol at C6 of galactopyranose with 18:1 or 18:0 fatty acid moieties of the sophorolipids [22].…”

Section: Discussionmentioning

confidence: 99%

Production and modification of bioactive biosurfactants

Langer

Palme

Wray

et al. 2006

Process Biochemistry

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The soil bacterium Tsukamurella spec. DSM 44370 produces a mixture of oligosaccharide lipids when cultivated on sunflower oil. In contrast cultivation with calendula oil as carbon source afforded a different product composition with overproduction of 2,3-di-O-acyl-ß-Dglucopyranosyl-(1-2)-ß-D-galactopyranosyl-(1-6)-4,6-di-O-acyl-α-D-glucopyranosyl-(1-1)-α-Dglucopyranose (GL 3) that amounted to 60 % of the whole product. GL3 and its parent tetrahexose backbone G 3 were then modified enzymatically with the lipase Novozyme 435 from Candida antarctica by addition of one and two oleic acid molecules to GL3 and four molecules to G 3. The new glycolipids were shown to exhibit interesting surface activities compared to commercially available products, decreasing the surface tension of water to 23 mN/m. In addition these products showed novel biological activities through the inhibition of the activation of Epstein-Barr virus early antigen.

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Enzyme-catalyzed regioselective transesterification of peracylated sophorolipids

Cited by 27 publications

References 25 publications

Cloning and functional characterization of the UDP‐glucosyltransferase UgtB1 involved in sophorolipid production by Candida bombicola and creation of a glucolipid‐producing yeast strain

Cloning and functional characterization of the UDP‐glucosyltransferase UgtB1 involved in sophorolipid production by Candida bombicola and creation of a glucolipid‐producing yeast strain

Enzymatic production of modified 2‐dodecyl‐sophorosides (biosurfactants) and their characterization

Production and modification of bioactive biosurfactants

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