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MetaCyc Pathway: sophorolipid degradation

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: sophorosyloxydocosanoate degradation

Superclasses: Degradation/Utilization/Assimilation Fatty Acid and Lipids Degradation

Some taxa known to possess this pathway include ? : Rhodotorula bogoriensis

Expected Taxonomic Range: Fungi

Summary:
Sophorosyloxydocosanoate is an extracellular glycolipid secreted by several yeasts including the ascomycete Starmerella bombicola (previously known as Candida bombicola) and the basidiomycete Rhodotorula bogoriensis (previously known as Candida bogoriensis ATCC 18809) [Nunez04][Fell00]. The function of this glycolipid is unknown, but glycolipids such as this are of interest for their biological activities and chemical properties. They are potentially useful in medical, cosmetic and chemical engineering applications. Chemical derivatives of biologically produced sophorolipids have been described [Singh03a].

Sophorolipids are relatively rare. They contain the glucose disaccharide sophorose, which has a glucosyl-β-(1,2)glucosyl linkage. sophorose is joined to a hydroxyl group of a hydroxy fatty acid aglycone (in [Esders72]). Analysis of the sophorolipids produced by Rhodotorula bogoriensis revealed des-, mono- and di-acetylated sophorose moieties, with the lipid in the free acid form. The majority of the hydroxy fatty acids had a chain length of 22 carbons, with <10% containing 24 carbons [Nunez04].

The biosynthesis of 13-sophorosyloxydocosanoate 6',6''-diacetate in Rhodotorula bogoriensis has been extensively studied by Light and co-workers (see MetaCyc pathway sophorolipid biosynthesis). They characterized three glycolipids produced by Rhodotorula bogoriensis cells as the diacetyl, monoacetyl and unacetylated forms of 13-[O(2')-β-D-glucopyranosyl-β-D-glucopyranosyloxy]docosanoate. An in vivo time course of production of these glycolipids in relation to growth phase suggested that the diacetyl derivative is formed first and is a precursor of the mono- and unacetylated forms. This indicated removal of acetyl groups from the diacetyl form. The glycolipids disappeared from older cultures, suggesting that they were either incorporated into other molecules, or degraded [Esders72a].

A catabolic acetylesterase having 13-sophorysyloxydocosanoate 6',6''-diacetate acetylhydrolase (acetylesterase) activity was purified from Rhodotorula bogoriensis cell extracts and partially characterized. Although it had the required activity in vitro, its broad substrate specificity makes conclusions about its in vivo role uncertain. It may also participate in other reactions [Bucholtz76].

Citations: [Overbeek98]

Credits:
Revised 31-Oct-2012 by Fulcher CA , SRI International


References

Bucholtz76: Bucholtz ML, Light RJ (1976). "Hydrolysis of 13-sophorosyloxydocosanoic acid esters by acetyl- and carboxylesterases isolated from Candida bororiensis." J Biol Chem 251(2);431-7. PMID: 1245482

Esders72: Esders TW, Light RJ (1972). "Glucosyl- and acetyltransferases involved in the biosynthesis of glycolipids from Candida bogoriensis." J Biol Chem 247(5);1375-86. PMID: 5012313

Esders72a: Esders TW, Light RJ (1972). "Characterization and in vivo production of three glycolipids from Candida Bogoriensis: 13-glucopyranosylglucopyranosyloxydocosanoic acid and its mono- and diacetylated derivatives." J Lipid Res 13(5);663-71. PMID: 5075510

Fell00: Fell JW, Boekhout T, Fonseca A, Scorzetti G, Statzell-Tallman A (2000). "Biodiversity and systematics of basidiomycetous yeasts as determined by large-subunit rDNA D1/D2 domain sequence analysis." Int J Syst Evol Microbiol 50 Pt 3;1351-71. PMID: 10843082

Nunez04: Nunez A, Ashby R, Foglia TA, Solaiman DK (2004). "LC/MS analysis and lipase modification of the sophorolipids produced by Rhodotorula bogoriensis." Biotechnol Lett 26(13);1087-93. PMID: 15218385

Overbeek98: Overbeek, R, Larsen, N, Selkov, EE, Maltsev, M "The WIT Database." 1998 WWW URL http://www.cme.msu.edu/WIT/.

Singh03a: Singh SK, Felse AP, Nunez A, Foglia TA, Gross RA (2003). "Regioselective enzyme-catalyzed synthesis of sophorolipid esters, amides, and multifunctional monomers." J Org Chem 68(14);5466-77. PMID: 12839437

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, BIOCYC13B.