Application of Transglycosylation Activity of Microbial Endoglycosidases to Syntheses of Bioactive Compounds
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- Yamamoto Kenji
- Graduate School of Biostudies, Kyoto University
Bibliographic Information
- Other Title
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- 微生物のエンドグリコシダーゼの糖転移活性を応用した生理活性物質の合成
- ビセイブツ ノ エンドグリコシダーゼ ノ トウ テンイ カッセイ オ オウヨウ シタ セイリ カッセイ ブッシツ ノ ゴウセイ ガン エイブン
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Abstract
Many glycosidases exhibit transglycosylation activities that involve the transfer of a carbohydrate moiety to the hydroxyl groups of various compounds, in addition to hydrolytic activities. We established the chemo-enzymatic synthesis of a glycopeptide using the transglycosylation activity of endo-β-N-acetylglucosaminidase of Mucor hiemalis (Endo-M). This method consists of the chemical synthesis of N-acetylglucosaminyl peptide and the transglycosylation of N-linked sugar chain from oligosaccharide donor to an N-acetylglucosaminyl peptide by Endo-M. We could add the sialo-complex-type oligosaccharide to bioactive peptides such as Peptide T and calcitonin by this method. We were also able to add the oligosaccharide to the glutamine residue of the Substance P neuropeptide and yeast α-mating factor. These glycosylated bioactive peptides showed a higher degree of resistance to protease digestion than original peptides.<br>By means of transglycosylation of Endo-M, we prepared glycopolymer containing multivalent oligosaccharides which can inhibit infection of influenza viruses to host cells. We also could exchange the high-mannose type of oligosaccharides in glycoproteins/glycopeptides to the complex types by the transglycosylation of Endo-M, and could synthesize novel glycolipids having a sugar chain of glycoprotein using the transglycosylation activity of Endo-M followed by preparation of a monoclonal antibody against the oligosaccharide of glycoprotein using the obtained glycolipid as immunogen.<br>Endo-α-N-acetylgalactosaminidase from Bifidobacterium longum exhibits transglycosylation activity. We succeeded in adding Galβ1, 3GalNAc from Galβ1, 3GalNAcα1pNP to 1-alchanol, monosaccharide and bioactive peptides containing a serine/threonine residue using this enzyme.
Journal
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- Trends in Glycoscience and Glycotechnology
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Trends in Glycoscience and Glycotechnology 18 (99), 49-62, 2006
FCCA(Forum: Carbohydrates Coming of Age)
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Details 詳細情報について
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- CRID
- 1390001204368843648
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- NII Article ID
- 10018117580
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- NII Book ID
- AA10995236
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- ISSN
- 18832113
- 09157352
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- NDL BIB ID
- 7920131
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed