cyclic β-1,3-heptaglucan | 1207955-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclic β-1,3-heptaglucan
• 英文别名: cL7
• CAS: 1207955-11-0
• 化学式: C₄₂H₇₀O₃₅
• 分子量: 1135.0
• InChiKey: GXRGXOIZGDLPNF-SSPKZVQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -15.23
• 重原子数：
  77.0
• 可旋转键数：
  7.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  554.05
• 氢给体数：
  21.0
• 氢受体数：
  35.0

反应信息

• 作为产物：
  描述：

  α-laminariheptaosyl fluoride 在 Phanerochaete chrysosporium laminarinase 16A variant E₁₁₅S 作用下， 反应 48.0h， 生成 cyclic β-1,3-heptaglucan 、 laminariheptaose
  参考文献：
  名称：

  Synthesis of Cyclic β-Glucan Using Laminarinase 16A Glycosynthase Mutant from the Basidiomycete Phanerochaete chrysosporium

  摘要：

  Glycosynthases are precise molecular instruments for making specifically linked oligosaccharides. X-ray crystallography screening of ligands bound to the 1,3(4)-beta-D-glucanase nucleophile mutant E115S of Phanerochaete chrysosporium Laminarinase 16A (Lam16A) showed that laminariheptaose (L7) bound in an arch with the reducing and nonreducing ends occupying either side of the catalytic cleft of the enzyme. The X-ray structure of Lam16A E115S in complex with alpha-laminariheptaosyl fluoride (alpha L7F) revealed how alpha L7F could make a nucleophilic attack upon itself. Indeed, when Lam16A E115S was allowed to react with alpha L7F the major product was a cyclic beta-1,3-heptaglucan, as shown by mass spectrometry. NMR confirmed uniquely beta-1,3-linkages and no reducing end. Molecular dynamics simulations indicate that the cyclic laminariheptaose molecule is not completely planar and that torsion angles at the glycosidic linkages fluctuate between two energy minima. This is the first report of a glycosynthase that joins the reducing and nonreducing ends of a single oligosaccharide and the first reported synthesis of cyclic beta-glucan.

  DOI：

  10.1021/ja909129b