Methyl (3,4-di-O-benzyl-2-acetimido-2-deoxy-β-D-glucopyranosyl)(1->2)-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,6-di-O-benzyl-α-D-mannopyranoside-4,6''-methylidene acetal | 245365-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl (3,4-di-O-benzyl-2-acetimido-2-deoxy-β-D-glucopyranosyl)(1->2)-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,6-di-O-benzyl-α-D-mannopyranoside-4,6''-methylidene acetal
• CAS: 245365-59-7
• 化学式: C₇₁H₇₉NO₁₆
• 分子量: 1202.41
• InChiKey: HQTPTKSGVUHMIP-PJFSTVDZSA-N

反应信息

• 作为反应物：
  描述：

  Methyl (3,4-di-O-benzyl-2-acetimido-2-deoxy-β-D-glucopyranosyl)(1->2)-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,6-di-O-benzyl-α-D-mannopyranoside-4,6''-methylidene acetal 在 palladium diacetate 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以90%的产率得到Methyl (2-acetimido-2-deoxy-β-D-glucopyranosyl)(1->2)-(α-D-mannopyranosyl)-(1->3)-α-D-mannopyranoside-4,6''-methylidene acetal
  参考文献：
  名称：

  Synthesis and Conformational Analysis of a Conformationally Constrained Trisaccharide, and Complexation Properties with Concanavalin A

  摘要：

  The trisaccharide beta-D-GlcNAc(1 --> 2)alpha-D-Man(1 --> 3)D-Man is a fragment of a biantennary glycan that is recognized by alpha-D-Man-specific lectins such as concanavalin A (ConA), Lathyrus ochrus lectin, lentil lectin, and can adopt several conformations upon binding. To probe the importance of loss of flexibility of a saccharide during binding with ConA this trisaccharide has been synthesized in a conformationally constrained form where a methylene acetal bridge mimics a GlcNAc-O-6 "...Man-O-4 intramolecular hydrogen bond. Microcalorimetry measurements revealed that the conformationally constrained compound has a more favorable entropy term but this term is offset by a smaller enthalpy term. NMR spectroscopic studies have shown that the cyclic compound is indeed considerably less flexible than the linear compound and both compounds adopt mainly one conformation. SYBYL software together with energy parameters appropriate for carbohydrates was used for a systematic conformational search. The linear compound is very flexible. A clustering method determined seven main conformational families. Six possible conformational families were identified for the cyclic compound when considering the orientations of the beta GlcNAc(1 --> 2)Man and alpha beta Man-(1 --> 3)Man glycosidic bonds. The central mannose residue was docked in the binding site of ConA and the complex was refined. The results are compared with crystal structures of legume lectin oligosaccharide complexes and with the NMR and thermodynamic data.

  DOI：

  10.1002/(sici)1521-3765(19990802)5:8<2281::aid-chem2281>3.0.co;2-d
• 作为产物：
  描述：

  Methyl (3,4-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)(1->2)-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,6-di-O-benzyl-α-D-mannopyranoside-4,6''-methylidene acetal 在 吡啶 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 Methyl (3,4-di-O-benzyl-2-acetimido-2-deoxy-β-D-glucopyranosyl)(1->2)-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,6-di-O-benzyl-α-D-mannopyranoside-4,6''-methylidene acetal
  参考文献：
  名称：

  Synthesis and Conformational Analysis of a Conformationally Constrained Trisaccharide, and Complexation Properties with Concanavalin A

  摘要：

  The trisaccharide beta-D-GlcNAc(1 --> 2)alpha-D-Man(1 --> 3)D-Man is a fragment of a biantennary glycan that is recognized by alpha-D-Man-specific lectins such as concanavalin A (ConA), Lathyrus ochrus lectin, lentil lectin, and can adopt several conformations upon binding. To probe the importance of loss of flexibility of a saccharide during binding with ConA this trisaccharide has been synthesized in a conformationally constrained form where a methylene acetal bridge mimics a GlcNAc-O-6 "...Man-O-4 intramolecular hydrogen bond. Microcalorimetry measurements revealed that the conformationally constrained compound has a more favorable entropy term but this term is offset by a smaller enthalpy term. NMR spectroscopic studies have shown that the cyclic compound is indeed considerably less flexible than the linear compound and both compounds adopt mainly one conformation. SYBYL software together with energy parameters appropriate for carbohydrates was used for a systematic conformational search. The linear compound is very flexible. A clustering method determined seven main conformational families. Six possible conformational families were identified for the cyclic compound when considering the orientations of the beta GlcNAc(1 --> 2)Man and alpha beta Man-(1 --> 3)Man glycosidic bonds. The central mannose residue was docked in the binding site of ConA and the complex was refined. The results are compared with crystal structures of legume lectin oligosaccharide complexes and with the NMR and thermodynamic data.

  DOI：

  10.1002/(sici)1521-3765(19990802)5:8<2281::aid-chem2281>3.0.co;2-d