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Chemo-enzymatic synthesis of 4-methylumbelliferyl beta-(1 -> 4)-D-xylooligosides: new substrates for beta-D-xylanase assays
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2005 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 3, no 1, 146-151 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2005. Vol. 3, no 1, 146-151 p.
Keyword [en]
enzymatic-synthesis, glycosides, transglycosylation, oligosaccharides, disaccharides, cellulases
URN: urn:nbn:se:kth:diva-14432DOI: 10.1039/b409583aISI: 000225738200020ScopusID: 2-s2.0-11844304068OAI: diva2:332473
QC 20100525Available from: 2010-08-05 Created: 2010-08-05Bibliographically approved

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