Lipase-mediated regioselective modifications of macrolactonic sophorolipids

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dc.contributor.authorSembayeva, Aliya
dc.contributor.authorBerhane, Beniam
dc.contributor.authorCarr, Jason A.
dc.creatorAliya, Sembayeva
dc.date.accessioned2017-12-20T03:16:28Z
dc.date.available2017-12-20T03:16:28Z
dc.date.issued2017-04-06
dc.description.abstractAbstract Chemoenzymatic synthesis and modification of well-defined macrolactonic sophorolipid (SLML) analogues via a series of successive regioselective de-esterification/transesterification reactions is investigated. Of the lipases screened, Candida antartica lipase- B (Novozyme-435) successfully deacylated the C-6′ acetoxy group of natural and peracylated SLMLs. Subsequent transesterification with acylating agents (esters of fatty acids) was successful only with the C-6′ deacetylated natural SLML providing an avenue to well-defined analogues of varying amphilicity. The macrolactonic motif was essential for enzymatic recognition of the sophorose rings of these complex glycolipids. In the absence of the lactonic motif, the peracylated sophorose rings are not deacylated, rather the carboxyl end of the non-lactonic forms that was preferentially transesterified. All macrolactonic derivatives were characterized by IR, 1H, 13C, 1H-1H and 1H-13C NMR spectroscopy, as well as HRMS where applicable.en_US
dc.identifierDOI:10.1016/j.tet.2017.02.043
dc.identifier.citationAliya Sembayeva, Beniam Berhane, Jason A. Carr, Lipase-mediated regioselective modifications of macrolactonic sophorolipids, In Tetrahedron, Volume 73, Issue 14, 2017, Pages 1873-1880en_US
dc.identifier.issn00404020
dc.identifier.urihttps://www.sciencedirect.com/science/article/pii/S0040402017301825
dc.identifier.urihttp://nur.nu.edu.kz/handle/123456789/2952
dc.language.isoenen_US
dc.publisherTetrahedronen_US
dc.relation.ispartofTetrahedron
dc.rights.license© 2017 Elsevier Ltd. All rights reserved.
dc.subjectSophorolipidsen_US
dc.subjectGlycolipidsen_US
dc.subjectLipasesen_US
dc.subjectNMR spectroscopyen_US
dc.subjectLactoneen_US
dc.subjectFatty acid estersen_US
dc.subjectBiosurfactanten_US
dc.titleLipase-mediated regioselective modifications of macrolactonic sophorolipidsen_US
dc.typeArticleen_US
elsevier.aggregationtypeJournal
elsevier.coverdate2017-04-06
elsevier.coverdisplaydate6 April 2017
elsevier.endingpage1880
elsevier.identifier.doi10.1016/j.tet.2017.02.043
elsevier.identifier.eid1-s2.0-S0040402017301825
elsevier.identifier.piiS0040-4020(17)30182-5
elsevier.identifier.scopusid85013924179
elsevier.issue.identifier14
elsevier.openaccess0
elsevier.openaccessarticlefalse
elsevier.openarchivearticlefalse
elsevier.startingpage1873
elsevier.teaserChemoenzymatic synthesis and modification of well-defined macrolactonic sophorolipid (SLML) analogues via a series of successive regioselective de-esterification/transesterification reactions is investigated....
elsevier.volume73
workflow.import.sourcescience

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