Enzymatic Synthesis of Sulfated Disaccharides using β-D-Galactosidase-catalyzed Transglycosylation

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  • MURATA Takeomi
    Department of Applied Biological Chemistry, Shizuoka University
  • KOSUGI Masaki
    Department of Applied Biological Chemistry, Shizuoka University
  • NAKAMURA Tadashi
    Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine
  • URASHIMA Tadasu
    Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine
  • USUI Taichi
    Department of Applied Biological Chemistry, Shizuoka University

書誌事項

タイトル別名
  • Enzymatic Synthesis of Sulfated Disaccharides using .BETA.-D-Galactosidase-catalyzed Transglycosylation.
  • Enzymatic Synthesis of Sulfated Disaccharides using ベータ D Galactosidase catalyzed Transglycosylation

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抄録

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 (S6Galβ-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 (S6Galβ1-4GlcNAc) 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 S6Galβ1-2Glc 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 S6Galβ1-2Glcα-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 (Glcβ-OMe) acceptor, S6Galβ1-3Glcβ-OMe and S6Galβ1-6Glcβ-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.

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