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

• Yamamoto Kenji

  Graduate School of Biostudies, Kyoto University

書誌事項

タイトル別名

• Application of Transglycosylation Activity of Microbial Endoglycosidases to Syntheses of Bioactive Compounds
• 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

抄録

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.

収録刊行物

• Ｔｒｅｎｄｓ　ｉｎ　Ｇｌｙｃｏｓｃｉｅｎｃｅ　ａｎｄ　Ｇｌｙｃｏｔｅｃｈｎｏｌｏｇｙ

  Ｔｒｅｎｄｓ　ｉｎ　Ｇｌｙｃｏｓｃｉｅｎｃｅ　ａｎｄ　Ｇｌｙｃｏｔｅｃｈｎｏｌｏｇｙ 18 (99), 49-62, 2006

  FCCA(Forum: Carbohydrates Coming of Age)

キーワード

• transglycosylation
• endo-β-N-acetylglucosaminidase
• endo-α-N-acetylgalactosaminidase
• bioactive glycopeptide
• glycosylation

詳細情報

• CRID: 1390001204368843648
• NII論文ID: 10018117580
• NII書誌ID: AA10995236
• DOI: 10.4052/tigg.18.49
• ISSN: 18832113
• ISSN: 09157352
• NDL書誌ID: 7920131
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I7920131
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可