Enzymatic synthesis of novel branched sugar alcohols mediated by the transglycosylation reaction of pullulan-hydrolyzing amylase II (TVA II) cloned from Thermoactinomyces vulgaris R-47

Transglycosylation reactions are useful for preserving a specific sugar structure during the synthesis of branched oligosaccharides. We have previously reported a panosyl unit transglycosylation reaction by pullulan-hydrolyzing amylase II (TVA II) cloned from Thermoactinomyces vulgaris R-47 (Tonozuk...

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Published in:Carbohydrate research 2011-09, Vol.346 (13), p.1842-1847
Main Authors: Shimura, Yoichiro, Oh, Keimei, Kon, Misaki, Yamamoto, Eri, Mizuno, Yoshinori, Adachi, Takashi, Abe, Tomomi, Tamogami, Shigeru, Fukushima, Jun, Inamoto, Tamio, Tonozuka, Takashi
Format: Article
Language:English
Subjects:
Amylase
Amylases - metabolism
Bacterial Proteins - metabolism
Glucans - metabolism
hydrolysis
Molecular Structure
mutants
Non-reducing sugar
Oligosaccharide
oligosaccharides
Panose
pullulan
sorbitol
Sugar Alcohols - metabolism
Thermoactinomyces
Thermoactinomyces - enzymology
Thermoactinomyces vulgaris
Transglycosylation reaction
xylitol
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Summary:Transglycosylation reactions are useful for preserving a specific sugar structure during the synthesis of branched oligosaccharides. We have previously reported a panosyl unit transglycosylation reaction by pullulan-hydrolyzing amylase II (TVA II) cloned from Thermoactinomyces vulgaris R-47 (Tonozuka et al., Carbohydr. Res., 1994, 261, 157–162). The acceptor specificity of the TVA II transglycosylation reaction was investigated using pullulan as the donor and sugar alcohols as the acceptor. TVA II transferred the α-panosyl unit to the C-1 hydroxyl group of meso-erythritol, C-1 and C-2 of xylitol, and C-1 and C-6 of d-sorbitol. TVA II differentiated between the sugar alcohols’ hydroxyl groups to produce five novel non-reducing branched oligosaccharides, 1-O-α-panosylerythritol, 1-O-α-panosylxylitol, 2-O-α-panosylxylitol, 1-O-α-panosylsorbitol, and 6-O-α-panosylsorbitol. The Trp356→Ala mutant showed similar transglycosylation reactions; however, panose production by the mutant was 4.0–4.5-fold higher than that of the wild type. This suggests that Trp356 is important for recognizing both water and the acceptor molecules in the transglycosylation and the hydrolysis reaction.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2011.05.030