heptakis[6-O-(N-acetyl-L-leucylglycyl)]-β-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptakis[6-O-(N-acetyl-L-leucylglycyl)]-β-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,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-10,15,20,25,30,35-hexakis[[2-[[(2S)-2-acetamido-4-methylpentanoyl]amino]acetyl]oxymethyl]-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methyl 2-[[(2S)-2-acetamido-4-methylpentanoyl]amino]acetate
• 化学式: C₁₁₂H₁₈₂N₁₄O₅₆
• 分子量: 2620.74
• InChiKey: UWBABGYDRAWAGS-XBAKQODNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.1
• 重原子数：
  182
• 可旋转键数：
  63
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  1000
• 氢给体数：
  28
• 氢受体数：
  56

反应信息

• 作为反应物：
  描述：

  氨基葡萄糖 、 heptakis[6-O-(N-acetyl-L-leucylglycyl)]-β-cyclodextrin 以 辛醇 、 水 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Design and synthesis of a new series of amphiphilic peptide-β-cyclodextrins as phase transfer carriers for glucosamine

  摘要：

  A new series of amphiphilic beta-cyclodextrins were designed and synthesized by grafting peptide chains on to all primary hydroxyl groups via ester bond formation. The desired amphiphilic structures have been produced from ester connection between the C-6 of beta-cyclodextrin and the carboxyl group of N-acetylated resides: H2N-Leu-COOH, H2N-Leu-Gly-COOH, H2N-Leu-Gly-Leu-COOH, and H2N-Leu-Gly-Leu-Gly-COOH (3a-d). The synthetic pathway involves selective bromination of all primary hydroxyls of beta-cyclodextrins and then substitution with the carboxylate moiety of the mentioned N-acetyl residues in the presence of DBU (1,8-diazabicyclo[5,4,0]undec-7-ene). The ability of the synthetic compounds for extraction and phase transfer of glucosamine, as a hydrophilic organic compound, was then studied. The results showed a considerable ability of these amphiphilic compounds for extraction and a selective tendency of 3c for phase transfer of glucosamine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.075
• 作为产物：
  描述：

  乙酰基-亮氨酰-甘氨酸 、 七(6-溴-6-脱氧)-beta-环糊精 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以62%的产率得到heptakis[6-O-(N-acetyl-L-leucylglycyl)]-β-cyclodextrin
  参考文献：
  名称：

  Design and synthesis of a new series of amphiphilic peptide-β-cyclodextrins as phase transfer carriers for glucosamine

  摘要：

  A new series of amphiphilic beta-cyclodextrins were designed and synthesized by grafting peptide chains on to all primary hydroxyl groups via ester bond formation. The desired amphiphilic structures have been produced from ester connection between the C-6 of beta-cyclodextrin and the carboxyl group of N-acetylated resides: H2N-Leu-COOH, H2N-Leu-Gly-COOH, H2N-Leu-Gly-Leu-COOH, and H2N-Leu-Gly-Leu-Gly-COOH (3a-d). The synthetic pathway involves selective bromination of all primary hydroxyls of beta-cyclodextrins and then substitution with the carboxylate moiety of the mentioned N-acetyl residues in the presence of DBU (1,8-diazabicyclo[5,4,0]undec-7-ene). The ability of the synthetic compounds for extraction and phase transfer of glucosamine, as a hydrophilic organic compound, was then studied. The results showed a considerable ability of these amphiphilic compounds for extraction and a selective tendency of 3c for phase transfer of glucosamine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.075

文献信息

• Design and synthesis of a new series of amphiphilic peptide-β-cyclodextrins as phase transfer carriers for glucosamine
  作者：Seyed Mohammad Seyedi、Hamid Sadeghian、Atena Jabbari、Amir Assadi、Hamideh Momeni

  DOI：10.1016/j.tet.2010.06.075

  日期：2010.8

  A new series of amphiphilic beta-cyclodextrins were designed and synthesized by grafting peptide chains on to all primary hydroxyl groups via ester bond formation. The desired amphiphilic structures have been produced from ester connection between the C-6 of beta-cyclodextrin and the carboxyl group of N-acetylated resides: H2N-Leu-COOH, H2N-Leu-Gly-COOH, H2N-Leu-Gly-Leu-COOH, and H2N-Leu-Gly-Leu-Gly-COOH (3a-d). The synthetic pathway involves selective bromination of all primary hydroxyls of beta-cyclodextrins and then substitution with the carboxylate moiety of the mentioned N-acetyl residues in the presence of DBU (1,8-diazabicyclo[5,4,0]undec-7-ene). The ability of the synthetic compounds for extraction and phase transfer of glucosamine, as a hydrophilic organic compound, was then studied. The results showed a considerable ability of these amphiphilic compounds for extraction and a selective tendency of 3c for phase transfer of glucosamine. (C) 2010 Elsevier Ltd. All rights reserved.