6-O-α-D-galactopyranosyl-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-galactopyranosyl-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,3R,4S,5R,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-LDLNDICVSA-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：

  γ-环糊精 、 α-D-melibiose 在 coffe bean α-galactosidase 作用下， 反应 48.0h， 生成 6-O-α-D-galactopyranosyl-γ-cyclodextrin
  参考文献：
  名称：

  Galactosylation of Cyclodextrins and Branched Cyclodextrins by α-Galactosidases

  摘要：

  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。

  DOI：

  10.1271/bbb.58.652

文献信息

• 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。
• Isolation and characterization of novel heterogeneous branched cyclomalto-oligosaccharides (cyclodextrins) produced by transgalactosylation with α-galactosidase from coffee bean
  作者：Kyoko Koizumi、Toshiko Tanimoto、Yasuyo Okada、Koji Hara、Koki Fujita、Hitoshi Hashimoto、Sumio Kitahata

  DOI：10.1016/0008-6215(95)00240-0

  日期：1995.11

  Transgalactosylated derivatives of cyclomalto-hexaose (alpha CD), -heptaose (beta CD), and -octaose (gamma CD) were synthesized by alpha-galactosidase from coffee bean using melibiose as a donor and alpha CD, beta CD or gamma CD as an acceptor. Mono- and di-O-alpha-D- galactosylated CDs were isolated and purified by HPLC. Their structures were elucidated by fast-atom bombardment mass spectrometry (FABMS)

  麦芽糖以α-半乳糖苷酶为原料，以半乳糖为供体，α-CD，β-CD或γ-CD为半乳糖，通过环半乳糖苷（αCD），-庚糖（βCD）和-八糖（γCD）的半乳糖基化衍生物合成。受体。分离出单-和二-O-α-D-半乳糖基化的CD，并通过HPLC纯化。通过快速原子轰击质谱（FABMS）和13C NMR光谱阐明了它们的结构。为结构测定6（1），6n-二-O-α-D-半乳糖基-CD的位置异构体，通过环糊精和葡聚糖转移酶的消化产物通过HPLC和FABMS分析。
• 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。