α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->4)-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->4)-D-glucopyranose
• 英文别名: 6-O-α-isomaltosylmaltose；α-D-Glc-(1->6)-α-D-Glc-(1->6)-α-D-Glc-(1->4)-D-Glc；Isomaltotriosylglucose；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]oxan-2-yl]methoxy]oxane-3,4,5-triol
• 化学式: C₂₄H₄₂O₂₁
• 分子量: 666.585
• InChiKey: ATSPLDSNUFFQBC-WNPOOKDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  348
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->4)-D-glucopyranose 在 Aspergillus niger amyloglucosidase 作用下， 反应 6.0h， 生成 麦芽糖
  参考文献：
  名称：

  Bioengineering of Leuconostoc mesenteroides Glucansucrases That Gives Selected Bond Formation for Glucan Synthesis and/or Acceptor-Product Synthesis

  摘要：

  The variations in glucosidic linkage specificity observed in products of different glucansucrases appear to be based on relatively small differences in amino acid sequences in their sugar-binding acceptor subsites. Various amino acid mutations near active sites of DSRBCB4 dextransucrase from Leuconostoc mesenteroides B-1299CB4 were constructed. A triple amino acid mutation (S642N/E643N/V644S) immediately next to the catalytic D641 (putative transition state stabilizing residue) converted DSRBCB4 enzyme from the synthesis of mainly alpha-(1 -> 6) dextran to the synthesis of alpha-(1 -> 6) glucan containing branches of alpha-(1 -> 3) and alpha-(1 -> 4) glucosidic linkages. The subsequent introduction of mutation V532P/V535I, located next to the catalytic D530 (nucleophile), resulted in the synthesis of an alpha-glucan containing increased branched alpha-(1 -> 4) glucosidic linkages (approximately 11%). The results indicate that mutagenesis can guide glucansucrase toward the synthesis of various oligosaccharides or novel polysaccharides with completely altered linkages without compromising high transglycosylation activity and efficiency.

  DOI：

  10.1021/jf104629g
• 作为产物：
  描述：

  panose 在 Aspergillus niger amyloglucosidase 、 Leuconostoc mesenteroides B-1299CB₄ dextransucrase DSRBCB₄ 、 calcium chloride 作用下， 反应 3.0h， 生成 α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->4)-D-glucopyranose
  参考文献：
  名称：

  Bioengineering of Leuconostoc mesenteroides Glucansucrases That Gives Selected Bond Formation for Glucan Synthesis and/or Acceptor-Product Synthesis

  摘要：

  The variations in glucosidic linkage specificity observed in products of different glucansucrases appear to be based on relatively small differences in amino acid sequences in their sugar-binding acceptor subsites. Various amino acid mutations near active sites of DSRBCB4 dextransucrase from Leuconostoc mesenteroides B-1299CB4 were constructed. A triple amino acid mutation (S642N/E643N/V644S) immediately next to the catalytic D641 (putative transition state stabilizing residue) converted DSRBCB4 enzyme from the synthesis of mainly alpha-(1 -> 6) dextran to the synthesis of alpha-(1 -> 6) glucan containing branches of alpha-(1 -> 3) and alpha-(1 -> 4) glucosidic linkages. The subsequent introduction of mutation V532P/V535I, located next to the catalytic D530 (nucleophile), resulted in the synthesis of an alpha-glucan containing increased branched alpha-(1 -> 4) glucosidic linkages (approximately 11%). The results indicate that mutagenesis can guide glucansucrase toward the synthesis of various oligosaccharides or novel polysaccharides with completely altered linkages without compromising high transglycosylation activity and efficiency.

  DOI：

  10.1021/jf104629g

文献信息

• Acceptor reactions of alternansucrase from Leuconostoc mesenteroides NRRL B-1355
  作者：Gregory L. Côté、John F. Fobyt

  DOI：10.1016/0008-6215(82)85013-1

  日期：1982.12

  Extracellular glucansucrases from various bacterial sources, including Leuconostoc mesenteroides, have been shown to catalyze the transfer of glucosyl groups from sucrose to low-molecular-weight acceptor sugars, forming a series of oligosaccharides. An extracellular glucansucrase recently isolated from Leuconostoc mesenteroides NRRL B-1355 synthesizes a polysaccharide consisting of alternating α-(1→6)-

  来自各种细菌来源的细胞外葡聚糖蔗糖，包括肠间叶亮葡菌，已显示出可将葡萄糖基团从蔗糖转移至低分子量受体糖，从而形成一系列寡糖。最近从肠膜肠球菌NRNR B-1355中分离出的一种细胞外葡糖苷酶合成了由交替的α-（1→6）-和α-（1→3）连接的d-葡萄糖残基组成的多糖。我们已经发现，在许多低分子量受体糖存在下，这种酶制剂能够形成α-（1→6）-和α-（1→3）-连接的受体产物。d-葡萄糖仅产生异麦芽糖，没有形成黑糖。相似地，甲基α-d-葡萄糖苷，甲基β-d-葡萄糖苷，麦芽糖和黑糖生成了甲基α-异麦芽糖苷，甲基β-异麦芽糖苷，panose和62-O-α-d-葡萄糖基黑麦芽糖，分别。然而，异麦芽糖同时给出了异麦芽三糖和32-O-α-d-葡萄糖基异麦芽糖。这些初始的受体产物也可以充当受体，并且较高dp产物的结构表明，只有当非还原性葡萄糖受体基团通过α-连接时，才形成（1→3）-α-d-糖苷键。 （
• Bioengineering of Leuconostoc mesenteroides Glucansucrases That Gives Selected Bond Formation for Glucan Synthesis and/or Acceptor-Product Synthesis
  作者：Hee Kyoung Kang、Atsuo Kimura、Doman Kim

  DOI：10.1021/jf104629g

  日期：2011.4.27

  The variations in glucosidic linkage specificity observed in products of different glucansucrases appear to be based on relatively small differences in amino acid sequences in their sugar-binding acceptor subsites. Various amino acid mutations near active sites of DSRBCB4 dextransucrase from Leuconostoc mesenteroides B-1299CB4 were constructed. A triple amino acid mutation (S642N/E643N/V644S) immediately next to the catalytic D641 (putative transition state stabilizing residue) converted DSRBCB4 enzyme from the synthesis of mainly alpha-(1 -> 6) dextran to the synthesis of alpha-(1 -> 6) glucan containing branches of alpha-(1 -> 3) and alpha-(1 -> 4) glucosidic linkages. The subsequent introduction of mutation V532P/V535I, located next to the catalytic D530 (nucleophile), resulted in the synthesis of an alpha-glucan containing increased branched alpha-(1 -> 4) glucosidic linkages (approximately 11%). The results indicate that mutagenesis can guide glucansucrase toward the synthesis of various oligosaccharides or novel polysaccharides with completely altered linkages without compromising high transglycosylation activity and efficiency.