O-α-D-glucopyranosyl-(1->4)-O-α-D-glucopyranosyl-(1->3)-O-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: O-α-D-glucopyranosyl-(1->4)-O-α-D-glucopyranosyl-(1->3)-O-α-D-glucopyranosyl-(1->4)-D-glucopyranose
• 英文别名: maltosyl α-1,3-maltose；Glc(a1-4)Glc(a1-3)Glc(a1-4)Glc；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₄H₄₂O₂₁
• 分子量: 666.585
• InChiKey: AFDQDPIWXNGUOF-QIDLYCGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.5
• 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：

  O-α-D-glucopyranosyl-(1->4)-O-α-D-glucopyranosyl-(1->3)-O-α-D-glucopyranosyl-(1->4)-D-glucopyranose 在 glucoamylase 作用下， 反应 4.0h， 生成 葡萄糖
  参考文献：
  名称：

  Transglycosylation properties of maltodextrin glucosidase (MalZ) from Escherichia coli and its application for synthesis of a nigerose-containing oligosaccharide

  摘要：

  The transglycosylation reaction of maltodextrin glucosidase (MalZ) cloned and purified from Escherichia coli K12 was characterized and applied to the synthesis of branched oligosaccharides. Purified MalZ preferentially catalyzed the hydrolysis of maltodextrin, gamma-cyclodextrin (CD), and cycloamylose (CA). In addition, when the enzyme was incubated with 5% maltotriose (G3), a series of transfer products were produced. The resulting major transfer products, annotated as T1, T2, and T3, were purified and their structures were determined by TLC, MALDI-TOF/MS, C-13 NMR, and enzymatic analysis. T1 was identified as a novel compound, maltosyl alpha-1,3-maltose, whereas T2 and T3 were determined to be isopanose and maltosyl-alpha-1,6-maltose, respectively. These results indicated that MalZ transferred sugar moiety mainly to C-3 or C-6-OH of glucose of the acceptor molecule. To obtain highly concentrated transfer products, the enzyme was reacted with 10% liquefied cornstarch, and then glucose and maltose were removed by immobilized yeast. The T1 content of the resulting reaction mixture reached 9.0%. The mixture of T1 containing a nigerose moiety can have an immunopotentiating effect on the human body and may be a potential functional sugar stuff. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2010.05.073
• 作为产物：
  描述：

  benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 20.0 ℃ 、3399.98 MPa 条件下， 以62%的产率得到O-α-D-glucopyranosyl-(1->4)-O-α-D-glucopyranosyl-(1->3)-O-α-D-glucopyranosyl-(1->4)-D-glucopyranose
  参考文献：
  名称：

  二乙氨基三氟化硫 (DAST)–三氟甲磺酸锡 (II)–四丁基高氯酸铵–三乙胺系统脱水糖基化

  摘要：

  通过使用由二乙氨基三氟化硫 (DAST)、三氟甲磺酸锡 (II)、四丁基高氯酸铵和三乙胺组成的缩合试剂系统，使用 2,3,4,6-四-O-苄基-D-吡喃葡萄糖进行脱水糖基化. 使用该系统，两种四糖，O-α-D-吡喃葡萄糖基-(1→4)-O-α-D-吡喃葡萄糖基-(1→3)-O-α-D-吡喃葡萄糖基-(1→4)-D -吡喃葡萄糖和 O-α-D-吡喃葡萄糖基-(1→3)-O-α-D-吡喃葡萄糖基-(1→4)-O-α-D-吡喃葡萄糖基-(1→4)-D-吡喃葡萄糖合成的。

  DOI：

  10.1246/bcsj.71.2893

文献信息

• Dehydrative Glycosylation by Diethylaminosulfur Trifluoride (DAST)–Tin(II) Trifluoromethanesulfonate–Tetrabutylammonium Perchlorate–Triethylamine System
  作者：Motoko Hirooka、Shinkiti Koto

  DOI：10.1246/bcsj.71.2893

  日期：1998.12

  Dehydrative glycosylation using 2,3,4,6-tetra-O-benzyl-D-glucopyranose was carried out by the use of a condensing reagent system composed of diethylaminosulfur trifluoride (DAST), tin(II) triflate, tetrabutylammonium perchlorate, and triethylamine. Using this system, two tetrasaccharides, O-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→3)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranose and O-α-D-glu

  通过使用由二乙氨基三氟化硫 (DAST)、三氟甲磺酸锡 (II)、四丁基高氯酸铵和三乙胺组成的缩合试剂系统，使用 2,3,4,6-四-O-苄基-D-吡喃葡萄糖进行脱水糖基化. 使用该系统，两种四糖，O-α-D-吡喃葡萄糖基-(1→4)-O-α-D-吡喃葡萄糖基-(1→3)-O-α-D-吡喃葡萄糖基-(1→4)-D -吡喃葡萄糖和 O-α-D-吡喃葡萄糖基-(1→3)-O-α-D-吡喃葡萄糖基-(1→4)-O-α-D-吡喃葡萄糖基-(1→4)-D-吡喃葡萄糖合成的。
• Transglycosylation properties of maltodextrin glucosidase (MalZ) from Escherichia coli and its application for synthesis of a nigerose-containing oligosaccharide
  作者：Kyung-Mo Song、Jae-Hoon Shim、Jong-Tae Park、Sung-Hee Kim、Young-Wan Kim、Winfried Boos、Kwan-Hwa Park

  DOI：10.1016/j.bbrc.2010.05.073

  日期：2010.6

  The transglycosylation reaction of maltodextrin glucosidase (MalZ) cloned and purified from Escherichia coli K12 was characterized and applied to the synthesis of branched oligosaccharides. Purified MalZ preferentially catalyzed the hydrolysis of maltodextrin, gamma-cyclodextrin (CD), and cycloamylose (CA). In addition, when the enzyme was incubated with 5% maltotriose (G3), a series of transfer products were produced. The resulting major transfer products, annotated as T1, T2, and T3, were purified and their structures were determined by TLC, MALDI-TOF/MS, C-13 NMR, and enzymatic analysis. T1 was identified as a novel compound, maltosyl alpha-1,3-maltose, whereas T2 and T3 were determined to be isopanose and maltosyl-alpha-1,6-maltose, respectively. These results indicated that MalZ transferred sugar moiety mainly to C-3 or C-6-OH of glucose of the acceptor molecule. To obtain highly concentrated transfer products, the enzyme was reacted with 10% liquefied cornstarch, and then glucose and maltose were removed by immobilized yeast. The T1 content of the resulting reaction mixture reached 9.0%. The mixture of T1 containing a nigerose moiety can have an immunopotentiating effect on the human body and may be a potential functional sugar stuff. (C) 2010 Elsevier Inc. All rights reserved.