6-O-(α-D-mannopyranosyl)-γ-cyclodextrin

• 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-mannopyranosyl)-γ-cyclodextrin
• 英文别名: (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,38R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-5,10,15,20,30,35,40-heptakis(hydroxymethyl)-25-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.23,6.28,11.213,16.218,21.223,26.228,31.233,36]hexapentacontane-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecol
• 化学式: C₅₄H₉₀O₄₅
• 分子量: 1459.28
• InChiKey: SPSGWVFQAVINCT-ICUOQONXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -18.8
• 重原子数：
  99
• 可旋转键数：
  11
• 环数：
  31.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  712
• 氢给体数：
  27
• 氢受体数：
  45

反应信息

• 作为产物：
  描述：

  6-O-(2,3,4,6-tetra-O-acetyl-D-mannopyranosyl)-γ-cyclodextrin peracetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 6-O-(α-D-mannopyranosyl)-γ-cyclodextrin
  参考文献：
  名称：

  使用三氯乙亚氨酸酯方法高效合成支链环寡糖的化学方法

  摘要：

  为了合成支链的环麦芽寡糖（环糊精，CD），研究了使用三氯乙酰亚氨酸酯方法的糖基化。我们检查了与CD环直接β相连的半乳糖基CD的化学合成方法，该方法无法通过酶催化反应进行合成。我们结合了糖基供体上的保护基，合成亚氨酸酯衍生物的催化剂和糖基化催化剂，制备了6-O-（d-半乳糖基）-γCD和6-O-（d-甘露糖基）-γCD作为基本模型化合物。 。通过HPLC和NMR光谱确定构型异构体。

  DOI：

  10.1081/car-120023472

文献信息

• Enzymatic Synthesis of Mannosyl-cyclodextrin by <i>α</i>-Mannosidase from Jack Bean
  作者：Kenichi Hamayasu、Koji Hara、Koki Fujita、Yukio Kondo、Hitoshi Hashimoto、Toshiko Tanimoto、Kyoko Koizumi、Hirofumi Nakano、Sumio Kitahata

  DOI：10.1271/bbb.61.825

  日期：1997.1

  Mannosylated derivatives of cyclodextrins (CDs), mannosyl-α, β, and γCD were synthesized from a mixture of mannose and α, β, and γCD by the reverse action of α-mannosidase from jack bean, respectively. Their structures were analyzed by FAB-MS and 13C-NMR spectroscopies, and they were identified as 6-O-α-d-mannosyl-α, β, and γCD. The optimum conditions for the production of 6-O-α-d-mannosyl-αCD by α-mannosidase were examined. Optimum pH and temperature were pH 4.5 and 60°C, respectively. Yield of mannosyl-αCD increased with increasing mannose concentration and reached more than 35% (mol/mol) at the concentration of 2 m mannose and 0.4 m  αCD.

  环糊精(CD)、甘露糖基-α、β和γCD的甘露糖化衍生物是通过来自刀豆的α-甘露糖苷酶的逆作用分别由甘露糖和α、β和γCD的混合物合成的。通过FAB-MS和13C-NMR光谱分析其结构，将其鉴定为6-O-α-d-甘露糖基-α、β和γCD。研究了α-甘露糖苷酶生产6-O-α-d-甘露糖基-αCD的最佳条件。最佳 pH 值和温度分别为 pH 4.5 和 60°C。甘露糖基-αCD 的产率随着甘露糖浓度的增加而增加，在 2 m 甘露糖和 0.4 m αCD 浓度下达到 35% (mol/mol) 以上。
• Efficient Chemical Syntheses of Branched Cyclomalto‐Oligosaccharides Using the Trichloroacetimidate Method
  作者：Akiko Ikuta、Toshiko Tanimoto、Kyoko Koizumi

  DOI：10.1081/car-120023472

  日期：2003.1.8

  Glycosylation using the trichloroacetimidate method was investigated in order to synthesize branched cyclomalto‐oligosaccharides (cyclodextrins, CDs). We examined the chemical syntheses of galactosyl CDs, directly β‐linked to the CD ring, which could not be synthesized by enzyme catalyzed reactions. We prepared 6‐O‐(d‐galactosyl)‐γCD and 6‐O‐(d‐mannosyl)‐γCD as basic model compounds using a combination

  为了合成支链的环麦芽寡糖（环糊精，CD），研究了使用三氯乙酰亚氨酸酯方法的糖基化。我们检查了与CD环直接β相连的半乳糖基CD的化学合成方法，该方法无法通过酶催化反应进行合成。我们结合了糖基供体上的保护基，合成亚氨酸酯衍生物的催化剂和糖基化催化剂，制备了6-O-（d-半乳糖基）-γCD和6-O-（d-甘露糖基）-γCD作为基本模型化合物。 。通过HPLC和NMR光谱确定构型异构体。