O-α-D-glucoryranosyl-(1->4)-O-<α-D-glucopyranosyl-(1->6)>-D-glucopyranose | 25218-29-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-α-D-glucoryranosyl-(1->4)-O-<α-D-glucopyranosyl-(1->6)>-D-glucopyranose
• 英文别名: α-D-glucopyranosyl-(1->4)-{α-D-glucopyranosyl-(1->6)}-D-glucopyranose；α-D-Glcp-(1->4)-[α-D-Glcp-(1->6)-]D-Glcp；4,6-di-O-(α-D-glucopyranosyl)-D-glucopyranose；isopanose；Glc(a1-4)[Glc(a1-6)]Glc；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4R,5R)-4,5,6-trihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 25218-29-5；87584-40-5；89396-21-4；95463-60-8；141316-11-2；141316-12-3
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: OMDQUFIYNPYJFM-UCFFOQEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  O-α-D-glucoryranosyl-(1->4)-O-<α-D-glucopyranosyl-(1->6)>-D-glucopyranose 在 Aspergillus niger amyloglucosidase 作用下， 反应 3.0h， 生成 葡萄糖 、 异麦芽糖
  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：

  在 氢气 作用下， 以64%的产率得到O-α-D-glucoryranosyl-(1->4)-O-<α-D-glucopyranosyl-(1->6)>-D-glucopyranose
  参考文献：
  名称：

  使用对硝基苯磺酰氯、三氟甲磺酸银、N,N-二甲基乙酰胺和三乙胺的混合物进行脱水 α-葡萄糖基化

  摘要：

  α-连接的二糖和三糖的立体选择性合成是通过使用 2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖和对硝基苯磺酰氯、三氟甲磺酸银、 N,N-二甲基乙酰胺和三乙胺的二氯甲烷溶液。

  DOI：

  10.1246/cl.1982.1039

文献信息

• A stereoselective α-glucosylation by use of a mixture of 4-nitrobenzenesulfonyl chloride, silver tri-fluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine
  作者：Shinkiti Koto、Naohiko Morishima、Miho Owa、Shonosuke Zen

  DOI：10.1016/0008-6215(84)85271-4

  日期：1984.7

  Abstract Stereoselective α-glucosylation of partially protected carbohydrates with 2,3,4,6-tetra-O-benzyl-α- d -glucopyranose in dichloromethane, in the presence of a quaternary mixture of 4-nitrobenzenesulfonyl chloride, silver tri-fluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine gave O-α- d -glucopyranosyl-(1→4)- and 1(1→6)-2-acetamido-2-deoxy- d -glucopyranose (N-acetylmaltosamine

  摘要在4-硝基苯磺酰氯，三氟甲磺酸银， N，N-二甲基乙酰胺和三乙胺得到O-α-d-吡喃葡萄糖基-（1→4）-和1（1→6）-2-乙酰氨基-2-脱氧-d-吡喃葡萄糖（N-乙酰基麦芽糖胺和N-乙酰基异麦芽糖胺）。描述了O-α-d-吡喃葡萄糖基-（1→4）-O- [α-d-吡喃葡萄糖基-（1→6）]-d-吡喃葡萄糖的分步合成。
• 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.
• DEHYDRATIVE α-GLUCOSYLATION USING A MIXTURE OF<i>p</i>-NITROBENZENESULFONYL CHLORIDE, SILVER TRIFLUOROMETHANESULFONATE,<i>N</i>,<i>N</i>-DIMETHYLACETAMIDE, AND TRIETHYLAMINE
  作者：Naohiko Morishima、Shinkiti Koto、Shonosuke Zen

  DOI：10.1246/cl.1982.1039

  日期：1982.7.5

  synthesis of α-linked di- and trisaccharides is performed by the one-stage glucosylation using 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose and a mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine in dichloromethane.

  α-连接的二糖和三糖的立体选择性合成是通过使用 2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖和对硝基苯磺酰氯、三氟甲磺酸银、 N,N-二甲基乙酰胺和三乙胺的二氯甲烷溶液。