An alpha 2,3-Sialyltransferase from Photobacterium sp. JT-ISH-224 Transfers N-Acetylneuraminic Acid to Both the O-2 and O-3' Hydroxyl Groups of Lactose

We found that alpha 2,3-sialyltransferase from Photobacterium sp. JT-ISH-224 produced a regio-mistaken sialyl-transferred by-product. Spectroscopic analysis of the purified by-product indicated that it contained two N-acetylneuraminic acids: one attached to the O-3' hydroxyl group of lactose, a...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2010-03, Vol.29 (2), p.51-60
Main Authors: Mine, Toshiki, Kajiwara, Hitomi, Murase, Takefumi, Kajihara, Yasuhiro, Yamamoto, Takeshi
Format: Article
Language:English
Subjects:
Photobacterium
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Summary:We found that alpha 2,3-sialyltransferase from Photobacterium sp. JT-ISH-224 produced a regio-mistaken sialyl-transferred by-product. Spectroscopic analysis of the purified by-product indicated that it contained two N-acetylneuraminic acids: one attached to the O-3' hydroxyl group of lactose, and the other attached to the O-2 hydroxyl group of lactose. The relative configuration between the C-1 and C-3 of the alpha -glucopyranose residue is superimposable with that between C-4 and C-2 of galactopyranoside. Therefore, formation of this by-product, designated 2,3'-disialyllactose, was simply rationalized as a regio-mistaken reaction of bacterial alpha 2,3-sialyltransferase. This finding indicates that this bacterial alpha 2,3-sialyltransferase has a possibility to synthesize several unusual sialosides.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328300903586422