6-O-α-D-glucopyranosylcyclomaltohexaose | 10058-19-2

• 物质功能分类: 化学试剂 - 有机试剂 - 环糊精
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-α-D-glucopyranosylcyclomaltohexaose
• 英文别名: glucosyl-α-CD；(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31R,32R,33R,34R,35R,36R,37R,38R,39R,40R,41R,42R)-5,10,15,20,25-pentakis(hydroxymethyl)-30-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.23,6.28,11.213,16.218,21.223,26]dotetracontane-31,32,33,34,35,36,37,38,39,40,41,42-dodecol
• CAS: 10058-19-2
• 化学式: C₄₂H₇₀O₃₅
• 分子量: 1135.0
• InChiKey: GIZQJUDQRHMFRK-AHIHXIOASA-N

物化性质

• 沸点：
  1519.6±65.0 °C(Predicted)
• 密度：
  1.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -14.5
• 重原子数：
  77
• 可旋转键数：
  9
• 环数：
  23.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  554
• 氢给体数：
  21
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  6-O-α-D-glucopyranosylcyclomaltohexaose 在 Sodium trimetaphosphate 作用下， 以 水 为溶剂， 反应 29.0h， 以29%的产率得到
  参考文献：
  名称：

  Stereoselective phosphorylation of branched cyclodextrins with inorganic cyclo-triphosphate

  摘要：

  The phosphorylation by inorganic sodium cyclo-triphosphate (P-3m) having a six-membered ring was examined for cyclomaltohexaose (alpha-cyclodextrin) and branched cyclodextrins (mono-6-O-alpha-D-glucopyranosylcyclomaltohexaose, mono-6-O-alpha-D-maltosylcyclomaltohexaose, mono-6-O-alpha-D-glucopyranosylcyclomaltoheptaose, and mono-6-O-alpha-D-maltosylcyclomaltoheptaose) in aqueous solution. For all cyclomaltooligosaccharides (cyclodextrins) studied, the 2-OH group was stereoselectively phosphorylated. In the reaction of branched cyclodextrins and P-3m, only the 2-OH on the alpha-D-glucopyranosyl group of the cyclodextrin rings was phosphorylated with maximum yields of more than 27%. The phosphorylation mechanism of branched cyclodextrins with P-3m is also discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00346-x
• 作为产物：
  描述：

  maltotriose 在 acetate buffer 、 异淀粉酶悬浮剂 、 glucoamylase 作用下， 反应 72.0h， 生成 6-O-α-D-glucopyranosylcyclomaltohexaose
  参考文献：
  名称：

  假单胞菌异淀粉酶水解和合成支化的环麦芽六糖

  摘要：

  摘要研究了假单胞菌异淀粉酶对具有不同长度侧链的支链环麦芽六糖（α-环糊精，cG 6 s）的作用，以及麦芽低聚糖（G 2 -G 7）和cG 6之间的反向缩合反应。在水解和缩合反应中，麦芽三糖的释放和附着的反应速率最大，并且活性随侧链长度的增加而降低。G 2-，G 3-，G 4-和G 5 -cG 6的水解反应的V max（U / mg）的值分别为2.6、690、320和290，K的值m（mm）分别为72、204、92和47。通过酶促分析，13 Cn.mr和fab鉴定了通过缩合反应获得的新的支链cG 6 s（G 4 -cG 6和G 5 -cG 6）的结构。-质谱。报道了这些支链cG 6的溶血活性。

  DOI：

  10.1016/0008-6215(89)80034-5

文献信息

• Galactosylation of Cyclodextrins and Branched Cyclodextrins by α-Galactosidases
  作者：Koji Hara、Koki Fujita、Nobuhiro Kuwahara、Toshiko Tanimoto、Hitoshi Hashimoto、Kyoko Koizumi、Sumio Kitahata

  DOI：10.1271/bbb.58.652

  日期：1994.1

  Transgalactosylated derivatives of cyclodextrins (CDs) and glucosyl and maltosyl CDs (G1- and G2-CDs) were synthesized by α-galactosidases from coffee bean and Mortierella vinacea (M. vinacea). The structures of the transfer products were analyzed by FAB-mass, 13C-NMR and methylation.Coffee bean α-galactosidase transferred a galactosyl residue not only to side chains of G1-CDs and G2-CDs, but also directly to CD rings. M. vinacea  α-galactosidase transferred a galactosyl residue only to side chains of G2-CDs.

  咖啡豆和葡萄孢霉（Mortierella vinacea）的α-半乳糖苷酶合成了环糊精（CD）以及葡萄糖基和麦芽糖基CD（G1-CD和G2-CD）的半乳糖基转移衍生物。咖啡豆α-半乳糖苷酶不仅能将半乳糖基残基转移到 G1-CDs 和 G2-CDs 的侧链上，还能直接转移到 CD 环上。葡萄孢α-半乳糖苷酶只将半乳糖基残基转移到 G2-CD 的侧链上。
• Synthesis of branched cyclomaltooligosaccharide carboxylic acids (cyclodextrin carboxylic acids) by microbial oxidation
  作者：Toshihiro Ishiguro、Takako Fuse、Masahide Oka、Takashi Kurasawa、Masanari Nakamichi、Yoshihiro Yasumura、Masahiko Tsuda、Takamasa Yamaguchi、Ikuo Nogami

  DOI：10.1016/s0008-6215(01)00053-2

  日期：2001.4

  (cyclodextrin carboxylic acid) derivatives were synthesized by microbial oxidation using Pseudogluconobacter saccharoketogenes to oxidize five types of branched cyclodextrins, including maltosyl beta-cyclodextrin (maltosyl-beta-CyD). For each novel cyclodextrin carboxylic acid derivative synthesized, the hydroxymethyl group of the terminal glucose residue in the branched part of the molecule was regiospecifically

  新型的支链环麦芽低聚糖羧酸衍生物（环糊精羧酸）衍生物是利用假葡糖杆菌糖原基因通过微生物氧化合成的，可氧化五种类型的支链环糊精，包括麦芽糖基β-环糊精（麦芽糖基-β-CyD）。对于每种合成的新型环糊精羧酸衍生物，将分子支链部分中末端葡萄糖残基的羟甲基区域特异性地氧化为羧基，得到相应的糖醛酸。此外，环麦芽庚糖基-（6-> 1）-α-D-吡喃葡萄糖基-（4-> 1）-α-D-吡喃葡糖醛糖醛酸（GUG-β-CyD）（1）及其钠的理化性质由于这些化合物最有可能实际应用，因此对其进行了更广泛的研究。
• Preparation, isolation, and characterization of novel heterogeneous branched cyclomalto-oligosaccharides having β-d-galactosyl residue(s) on the side chain
  作者：Kyoko Koizumi、Toshiko Tanimoto、Koki Fujita、Koji Hara、Nobuhiro Kuwahara、Sumio Kitahata

  DOI：10.1016/0008-6215(93)87006-e

  日期：1993.1

  Transgalactosylated products of branched cyclodextrins (glucosyl-alphaCD, -betaCD, -gammaCD, and maltosyl-alphaCD, -betaCD, -gammaCD)were synthesized by beta-D-galactosidases from Bacillus circulans and Penicillium multicolor using lactose as a donor substrate and branched CDs as acceptors. Eighteen beta-D-galactosylated branched CDs were isolated and purified by HPLC. Their structures were elucidated by FABMS and C-13 NMR spectroscopies, and methylation analysis. The chromatographic behavior of these novel heterogeneous branched CDs on three HPLC columns of different separation modes was compared.
• Sakano, Yoshiyuki; Sano, Mutsumi; Kobayashi, Tsuneo, Agricultural and Biological Chemistry, 1985, vol. 49, # 12, p. 3391 - 3398
  作者：Sakano, Yoshiyuki、Sano, Mutsumi、Kobayashi, Tsuneo

  DOI：——

  日期：——
• Two-dimensional n.m.r. spectra of 6- O -α- d -glucopyranosylcyclomalto-hexaose; 1 H and 13 C resonance assignments and primary structure determination
  作者：Yasuhiko Yamamoto、Yoshio Inoue、Riichrô Chûjô、Shoichi Kobayashi

  DOI：10.1016/0008-6215(87)80052-6

  日期：1987.8