PMID: 8585609Sep 1, 1995Paper

Tandem mass spectrometry and nuclear magnetic resonance spectroscopy studies of Candida bombicola sophorolipids and product formed on hydrolysis by cutinase

Analytical Biochemistry
C G de KosterJ Haverkamp

Abstract

Natural mixtures of sophorolipids produced by the yeast Candida bombicola have been analyzed by fast atom bombardment (FAB)-MS and collision-induced dissociation (CID)-MS. Some pure components have been analysed by two-dimensional NMR spectroscopy. The presence of acidic, lactonic, and O-acetylated forms and the position of double bonds in the fatty acid part of these glycolipids can be easily inferred from positive and negative ion FAB-mass spectra. Details about position of O-acetylation can be obtained from CID mass spectra of [M+H]+ and [M-H]- ions and from the NMR spectra. Differences in CID fragmentation between protonated and sodiated molecular ions are discussed in detail. Enzymatic hydrolysis of 6',6"-di-O-acetyl sophorolipid lactone by cutinase from Fusarium solani results specifically in the removal of the 6'-O-acetyl group, whereas the 6"-O-acetyl and lactone group are resistant. This specificity is explained from a three-dimensional model of the sophorolipid generated on the basis of the short 1H,1H distances as inferred from the NMR (ROESY) spectra.

Citations

Aug 8, 2008·Bioscience, Biotechnology, and Biochemistry·Jiraporn ThaniyavarnSuthep Thaniyavarn
Feb 28, 2016·Enzyme and Microbial Technology·Tom Tao Huang, John M Wages
Jul 19, 2013·The Journal of General and Applied Microbiology·Kasturi DuttaVeeranki Venkata Dasu
Jan 15, 2002·Biotechnology and Bioengineering·Vladimir GuilmanovRichard A Gross
May 4, 2007·Applied Microbiology and Biotechnology·Inge N A Van BogaertErick J Vandamme
May 31, 2012·ACS Nano·Niki BaccileInge Van Bogaert
Jul 4, 2003·The Journal of Organic Chemistry·Sanjay K SinghRichard A Gross

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