Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: cell wall
The structure was elucidated in this paperPublication DOI: 10.1016/j.carres.2004.03.008Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: huanghgl226.student
sina.com, huanghgl226
sina.com
Institutions: School of Life Science and Technology, Huazhong University of Science and Technology (East Campus), 1037 Luoyu Lu, Wuhan 430074, China, School of Chemistry, Central China Normal University, 100 Luoyu Lu, Wuhan, 430079, China
We describe a approach for the synthesis of a mixture of 3,4-epoxybutyl (1→3)-β-D-oligoglucosides. The particular (1→3)-β-D-glucan isolated from the cell walls of Saccharomyces cerevisiae was recovered from the aqueous medium as water-insoluble particles by the spray drying (GS) method, and it was characterized by FTIR spectroscopy. The acid-solubilized (1→3)-β-D-oligoglucosides were prepared by partial acid hydrolysis of glucan particles, which were qualitatively analyzed by fluorophore-assisted carbohydrate electrophoresis (FACE). The peracetylated 3-butenyl (1→3)-β-D-oligoglucosides were synthesized by treating peracetylated (1→3)-β-D-oligoglucosides with the 3-butenyl alcohols and a Lewis acid (SnCl4) catalyst. Epoxidation of the peracetylated 3-butenyl oligoglucosides took place with m-chloroperoxybenzoic acid (m-CPBA). NaOMe in dry methanol was used for the deacetylation of the blocked derivatives, to give the 3,4-epoxybutyl (1→3)-β-D-oligoglucoside mixture in an overall yield of 21%. The sample was analyzed by positive-ion electrospray ionization mass spectrometry (ESIMS). In a 3,4-epoxybutyl (1→3)-β-D-oligoglucoside-binding (1→3)-β-D-glucanase assay, we found that the (1→3)-β-D-glucanase was obviously inactivated by the 3,4-epoxybutyl (1→3)-β-D-oligoglucosides. At the same time, we found the 3,4-epoxybutyl (1→3)-β-D-oligoglucoside mixture was more active as compared to the underivatized oligoglucoside mixture in eliciting phytoalexin accumulation in tobacco cotyledon tissue. Furthermore, it could be kept for a longer time than a (1→3)-β-D-oligoglucoside mixture, which indicated it is much more stable than (1→3)-β-D-oligoglucosides.
synthesis, 3, 4-epoxybutyl (1→3)-β-D-oligoglucosides, (1→3)-β-D-glucanase-binding ability, phytoalexin-elicitor activity
Structure type: homopolymer ; n=3-9
Location inside paper: abstract, p.1455, scheme 1
Trivial name: (1-3)-β-D-oligoglucoside
Contained glycoepitopes: IEDB_1397514,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_161166,IEDB_2278476,IEDB_2278477,IEDB_558869,IEDB_857743,IEDB_983931,SB_192
Methods: partial acid hydrolysis, ESI-MS, chemical methods, FTIR, electrophoresis, enzyme assay, glycosylation, acetylation, biological activity assays
Biological activity: binding and phytoalexin-elicitor activity of (1-3)-b-D-oligosaccharides mixture and its epoxyalkyl derivatives
Enzymes that release or process the structure: 1,3-b-D-gluconase from Helix pomatia
Comments, role: 3,4-epoxybutylglycoside synthesis is described
Related record ID(s): 43702
NCBI Taxonomy refs (TaxIDs): 4932Reference(s) to other database(s): GTC:G51056AN
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error