Enzymatic synthesis of sulfated disaccharides using β-D-galactosidase-catalyzed transglycosylation

Article abstract of DOI:10.1271/bbb.65.2456

We have established a unique enzymatic approach for obtaining sulfated disaccharides using Bacillus circulans β-D-galactosidase-catalyzed 6-sulfo galactosylation. When 4-methyl umbelliferyl 6-sulfo β-D-galactopyranoside (S6Gal β-4MU) was used as a donor, the enzyme induced transfer of 6-sulfo galactosyl residue to GlcNAc acceptor. As a result, the desired compound 6′-sulfo N-acetyllactosamine (S6Gal β1-4GlcNAc) and its positional isomer 6′-sulfo N-acetylisolactosamine (S6Gal β1-6GlcNAc) were observed by HPAEC-PAD, in 49% total yield based on the donor added, and in a molar ratio of 1:3.5. With a glucose acceptor, the regioselectivity was substantially changed and S6Gal β1-2Glc was mainly produced along with β-(1-1)α, β-(1-3), β-(1-6) isomers in 74% total yield. When methyl α-D-glucopyranoside (Glcα-OMe) was an acceptor, the enzyme also formed mainly S6Gal β1-2Glcβ-OMe with its β-(1-6)-linked isomer in 41% total yield based on the donor added. In both cases, it led to the predominant formation of β-(1-2)-linked disaccharides. In contrast, with the corresponding methyl β-D-glucopyranoside (Glc β-OMe) acceptor, S6Gal β1-3Glc β-OMe and S6Gal β1-6Glc β-OMe were formed in a low total yield of 12%. These results indicate that the regioselectivity and efficiency on the β-D-galactosidase-mediated transfer reaction significantly depend on the anomeric configuration in the glucosyl acceptors.

Full text of DOI:10.1271/bbb.65.2456

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Enzymatic Synthesis of Sulfated Disaccharides using
β-D-Galactosidase-catalyzed Transglycosylation
Takeomi MURATAa, Masaki KOSUGIa, Tadashi NAKAMURAb, Tadasu URASHIMAb & Taichi
USUIa
a Department of Applied Biological Chemistry, Shizuoka University
b Department of Bioresource Science, Obihiro University of Agriculture and Veterinary
Medicine
Published online: 22 May 2014.
To cite this article: Takeomi MURATA, Masaki KOSUGI, Tadashi NAKAMURA, Tadasu URASHIMA & Taichi USUI (2001)
Enzymatic Synthesis of Sulfated Disaccharides using β-D-Galactosidase-catalyzed Transglycosylation, Bioscience,
Biotechnology, and Biochemistry, 65:11, 2456-2464, DOI: 10.1271/bbb.65.2456
To link to this article: http://dx.doi.org/10.1271/bbb.65.2456
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