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Chemo-enzymatic synthesis of 4-methylumbelliferyl beta-(1 -> 4)-D-xylooligosides: new substrates for beta-D-xylanase assays

TitleChemo-enzymatic synthesis of 4-methylumbelliferyl beta-(1 -> 4)-D-xylooligosides: new substrates for beta-D-xylanase assays
Publication TypeJournal Article
Year of Publication2005
AuthorsEneyskaya, EV, Ivanen, DR, Shabalin, KA, Kulminskaya, AA, Backinowsky, LV, Brumer, H, Neustroev, KN
JournalORGANIC & BIOMOLECULAR CHEMISTRY
Volume3
Pagination146-151
Type of ArticleArticle
ISSN1477-0520
Abstract

Transglycosylation catalyzed by a beta-D-xylosidase from Aspergillus sp. was used to synthesize a set of 4-methylumbelliferyl (MU) beta-1–>4-D-xylooligosides having the common structure {[}beta-D-Xyl-(1–>4)](2-5)-beta- D-Xyl-MU. MU xylobioside synthesized chemically by the condensation of protected MU beta-D-xylopyranoside with ethyl 2,3,4-tri-O-acetyl-1-thio-beta-D-xylopyranoside was used as a substrate for transglycosylation with the beta-D- xylosidase from Aspergillus sp. to produce higher MU xylooligosides. The structures of oligosaccharides obtained were established by H-1 and C-13 NMR spectroscopy and electrospray tandem mass spectrometry. MU beta-D-xylooligosides synthesized were tested as fluorogenic substrates for the GH-10 family beta-D-xylanase from Aspergillus orizae and the GH-11 family beta-D- xylanase I from Trichoderma reesei. Both xylanases released the aglycone from MU xylobioside and the corresponding trioside. With substrates having d.p. 4 and 5, the enzymes manifested endolytic activities, splitting off MU, MUX, and MUX2 primarily.

DOI10.1039/b409583a