Design and chemoenzymatic synthesis of thiooligosaccharide inhibitors of 1,3:1,4-β-D-glucanases

Vincent Moreau, Josep Lluis Viladot, Eric Samain, Antoni Planas, Hugues Driguez

Producción científica: Artículo en revista indizadaArtículorevisión exhaustiva

25 Citas (Scopus)

Resumen

A successful chemoenzymatic synthesis of oligosaccharides with an interglucosidic sulfur atom as inhibitors of 1,3:1,4-β-D-glucanases is described. The key compound 3a was synthesized from acetylated 1-thio-β-laminaribiose 4 and the methyl 4'-O-triflyl-lactoside 5. After de-O-acylation, the tetrasaccharide 3b was used as an acceptor and glucose-1-P as a donor in a phosphorolytic elongation catalysed by cellodextrin phosphorylase from Clostridium thermocellum. The expected pentasaccharide 2a and hexasaccharide 1 were isolated in 56% and 13% yield, respectively. As expected, the thiooligosaccharides 1, 2a, and 3b were resistant to enzymatic cleavage by 1,3:1,4-β-D-glucanase isolated from Bacillus licheniformis. Furthermore, they have been shown to act as competitive inhibitors of the hydrolysis of the chromophoric trisaccharide substrate 11 by this enzyme.

Idioma originalInglés
Páginas (desde-hasta)1849-1855
Número de páginas7
PublicaciónBioorganic and Medicinal Chemistry
Volumen4
N.º11
DOI
EstadoPublicada - nov 1996

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