2-[2-[bis(carboxymethyl)amino]ethyl-[[(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)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-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]amino]acetic acid | 1015776-99-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2-[bis(carboxymethyl)amino]ethyl-[[(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)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-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]amino]acetic acid
• CAS: 1015776-99-4
• 化学式: C₅₀H₈₂N₂O₄₀
• 分子量: 1351.19
• InChiKey: UKEMUEBMYYCISE-ZERPHKHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -20
• 重原子数：
  92
• 可旋转键数：
  17
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  652
• 氢给体数：
  23
• 氢受体数：
  42

反应信息

• 作为产物：
  描述：

  mono-6-deoxy-6-(2-aminoethylamino)-β-cyclodextrin 、 氯乙酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以66%的产率得到2-[2-[bis(carboxymethyl)amino]ethyl-[[(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)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-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]amino]acetic acid
  参考文献：
  名称：

  1H NMR studies of enantioselective host–guest complexation by modified β-cyclodextrins and their europium(III) complexes

  摘要：

  The enantioselectivity of mono-substituted beta-cyclodextrins 6(A)-[bis(carboxylatomethyl)amino]-6(A)-deoxy-beta-cyclodextrin, 6 beta CDidaH(2), (2(A)S,3(A)S)-3(A)-[bis(carboxylatomethyl)amino]-3(A)-deoxy-beta-cyclodextrin, 3 beta CDidaH(2), 6(A)-[tris(carboxylatomethyl)(2-aminoethyl)amino]-6(A)-deoxy-beta-cyclodextrin, 6 beta CDedtaH(3), and their Eu(3+) complexes in the formation of host-guest complexes with six enantiomeric guests in D(2)O have been studied by (1)H NMR 600 MHz spectroscopy. The guests are D/L-tryptophanate, D/L-Trp(-), D/L-4hydroxyphenylglycinate, D/L-4HOPhg(-), D/L-histidinate, D/L-His(-), D/L-pheniramine, D/L-Phm/D/L-PhmH(+), D/L-phenylglycinate, D/L-Phg(-), and D/L-beta-phenylserinate D/L-beta Phs(-). Enantioselective host-guest complexation occurs between [Eu(3 beta CDida](+), [Eu(6 beta CDida)](+), and [Eu(6 beta CDedta)] and D/L-Trp(-), [Eu(3 beta CDida)](+) and [Eu(6 beta CDida)](+) and D/L-4HOPhg(-), and beta CD, 3 beta CDida(2-), 6 beta CDida(2-), 6 beta CDedta(3-), [Eu(3 beta CDida)](+), [Eu(6 beta CDida)](+), and [EU(6 beta CDedta)] and D/L-Phm/D/L-PhmH(+). While host-guest complexation occurs for D/L-His(-) and D/L-Phg(-), no enantioselectivity is apparent. Host guest complexation occurs in the D/L-beta Phs(-) systems but their spectra are too complex for reliable analysis. The preparation of 3 beta CDidaH(2) and 6 beta CDedtaH(3) and the determination of their pK(a)s are also reported. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.12.005

文献信息

• 1H NMR studies of enantioselective host–guest complexation by modified β-cyclodextrins and their europium(III) complexes
  作者：Duc-Truc Pham、Philip Clements、Christopher J. Easton、Stephen F. Lincoln

  DOI：10.1016/j.tetasy.2007.12.005

  日期：2008.2

  The enantioselectivity of mono-substituted beta-cyclodextrins 6(A)-[bis(carboxylatomethyl)amino]-6(A)-deoxy-beta-cyclodextrin, 6 beta CDidaH(2), (2(A)S,3(A)S)-3(A)-[bis(carboxylatomethyl)amino]-3(A)-deoxy-beta-cyclodextrin, 3 beta CDidaH(2), 6(A)-[tris(carboxylatomethyl)(2-aminoethyl)amino]-6(A)-deoxy-beta-cyclodextrin, 6 beta CDedtaH(3), and their Eu(3+) complexes in the formation of host-guest complexes with six enantiomeric guests in D(2)O have been studied by (1)H NMR 600 MHz spectroscopy. The guests are D/L-tryptophanate, D/L-Trp(-), D/L-4hydroxyphenylglycinate, D/L-4HOPhg(-), D/L-histidinate, D/L-His(-), D/L-pheniramine, D/L-Phm/D/L-PhmH(+), D/L-phenylglycinate, D/L-Phg(-), and D/L-beta-phenylserinate D/L-beta Phs(-). Enantioselective host-guest complexation occurs between [Eu(3 beta CDida](+), [Eu(6 beta CDida)](+), and [Eu(6 beta CDedta)] and D/L-Trp(-), [Eu(3 beta CDida)](+) and [Eu(6 beta CDida)](+) and D/L-4HOPhg(-), and beta CD, 3 beta CDida(2-), 6 beta CDida(2-), 6 beta CDedta(3-), [Eu(3 beta CDida)](+), [Eu(6 beta CDida)](+), and [EU(6 beta CDedta)] and D/L-Phm/D/L-PhmH(+). While host-guest complexation occurs for D/L-His(-) and D/L-Phg(-), no enantioselectivity is apparent. Host guest complexation occurs in the D/L-beta Phs(-) systems but their spectra are too complex for reliable analysis. The preparation of 3 beta CDidaH(2) and 6 beta CDedtaH(3) and the determination of their pK(a)s are also reported. (C) 2007 Elsevier Ltd. All rights reserved.