Lipase-mediated regioselective modifications of macrolactonic sophorolipids

Aliya Sembayeva, Beniam Berhane, Jason Alexander Carr

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1873-1880
Number of pages8
JournalTetrahedron
Volume73
Issue number14
DOIs
StatePublished - Jan 1 2017
Externally publishedYes

Fingerprint

Transesterification
Lipase
Candida
Esterification
Glycolipids
Nuclear magnetic resonance spectroscopy
Esters
Magnetic Resonance Spectroscopy
Fatty Acids
Derivatives
sophorose
Novozyme 435
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy

Keywords

  • Biosurfactant
  • Fatty acid esters
  • Glycolipids
  • Lactone
  • Lipases
  • NMR spectroscopy
  • Sophorolipids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Lipase-mediated regioselective modifications of macrolactonic sophorolipids. / Sembayeva, Aliya; Berhane, Beniam; Carr, Jason Alexander.

In: Tetrahedron, Vol. 73, No. 14, 01.01.2017, p. 1873-1880.

Research output: Contribution to journalArticle

Sembayeva, Aliya ; Berhane, Beniam ; Carr, Jason Alexander. / Lipase-mediated regioselective modifications of macrolactonic sophorolipids. In: Tetrahedron. 2017 ; Vol. 73, No. 14. pp. 1873-1880.
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