Regioselective Synthesis of Sugar-chain Unit Involved in Glycoconjugate by Glycosidase

糖苷酶区域选择性合成糖复合物中涉及的糖链单元

• 批准号: 02806017
• 负责人: USUI Taichi
• 金额: $ 1.15万
• 依托单位: Shizuoka University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1990
• 资助国家: 日本
• 起止时间: 1990 至 1991
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-02806017/
• 关键词: Glycoconjugate; Transglycosylation; Regioselective Synthesis; Glycosidase; N-acetyllactosamine; Regioselective Synthesis; Nーacetyllactosamine; 複合糖質; 糖鎖認識単位; 酵素合成

N-Acetyllactosamine 1(Gal beta1-4GlcNAe)is known as a representative disaccharide which is itself important as a core component in oligosaccharide moieties of glycoproteins and glycolipids. Owing to the growing need for substantial amount of 1 as a biomaterial, we have developed a practical route for the synthetic of 1 from lactose and Nacetylglucosamine(GlcNAc), utilizing the transglycosylation reaction through beta-D-galactosidase from Bacillus circulans. Furthermore, utilization of the transglycosylation by B. circulans beta-D-galactosidase led to the synthesis of beta-(1-4)linked disaccharides and trisaccharides containing a 2-acetamido-2-deoxy-D-hexose. The derivative s of GlcNAe and GalNAc were used as acceptors for the preparations. The enzyme reaction was efficient enough to allow us to perform the one pot preparation of beta-(1-4)-linked galactosyl-oligosaccharide from lactose. With the enzyme, D-galacosyl transfer occurred preferentially at the C-4 position of GlcNAc and of GalNAc, respectively, of the configuration of the hydroxyl group.

N-乙酰乳糖胺1(Gal beta1-4GlcNAe)被认为是一种代表性的二糖，其本身作为糖蛋白和糖脂的寡糖部分的核心成分很重要。由于对作为生物材料的大量 1 的需求不断增长，我们开发了一条利用乳糖和 N 乙酰氨基葡萄糖 (GlcNAc) 合成 1 的实用路线，利用来自环状芽孢杆菌的 β-D-半乳糖苷酶的转糖基反应。此外，利用环状芽孢杆菌β-D-半乳糖苷酶的转糖基作用导致合成含有2-乙酰氨基-2-脱氧-D-己糖的β-(1-4)连接的二糖和三糖。 GlcNAe 和 GalNAc 的衍生物用作制剂的受体。酶反应足够有效，使我们能够从乳糖中一锅制备 β-(1-4)-连接的半乳​​糖基低聚糖。使用该酶，D-半乳糖基转移优先发生在GlcNAc和GalNAc的羟基构型的C-4位置上。

项目成果

T.Usui et al.: "Enzymatic syntheses of Nーacetyllactosamine and Nーacetylallolactosamine by the use of βーDーgalactosidases" submitted to Biochim.Biophys.Acta.

T. Usui 等人：“使用 β-D-半乳糖苷酶酶促合成 N-乙酰基乳糖胺和 N-乙酰基乳糖胺”，提交给 Biochim.Biophys.Acta。

T.Usui,H.Ohi,S.Kubota and Y.Ishido: "Enzymatic Synthesis of N-Acetyllactosamine and its Related Compounds by Glycosidase" Glycoconjugate J.8. 272 (1991)

T.Usui、H.Ohi、S.Kubota 和 Y.Ishido：“通过糖苷酶酶促合成 N-乙酰乳糖胺及其相关化合物”糖缀合物 J.8。

T.Usui: "Regioselective Synthesis of Useful Oligosaccharides by Glycosidase" Trends in Glycoscience and Glycotechnology. 4. 116-122 (1992)

T.Usui：“通过糖苷酶区域选择性合成有用的寡糖”糖科学和糖技术的趋势。

T.Usui: "Regioselactive Synthesis of Useful Oligosaccharides by Glycosidase" Trends in Glycoscience and Glycotechnology. 4. 116-122 (1992)

T.Usui：“通过糖苷酶区域选择性合成有用的寡糖”糖科学和糖技术的趋势。

T. Usui, H. Ohi, S. Kubota and Y. Ishido: "Enzymatic Synthesis of N-Acetyllactosamine and its Related Compounds by Glycosidase" 8. 272 (1991)

T. Usui、H. Ohi、S. Kubota 和 Y. Ishido：“通过糖苷酶酶促合成 N-乙酰乳糖胺及其相关化合物”8. 272 (1991)