1-(diaminomethylidene)-2-[[(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]guanidine | 1584978-73-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(diaminomethylidene)-2-[[(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]guanidine
• CAS: 1584978-73-3
• 化学式: C₄₄H₇₅N₅O₃₄
• 分子量: 1218.09
• InChiKey: QBYLWYBYKWAHEJ-FOUAGVGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -16.4
• 重原子数：
  83
• 可旋转键数：
  9
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  637
• 氢给体数：
  23
• 氢受体数：
  35

反应信息

• 作为产物：
  描述：

  单-6-O-氨基-Β-环糊精 、 N-amidinopyrazole-1-carboxamidine hydrochloride 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以16%的产率得到1-(diaminomethylidene)-2-[[(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]guanidine
  参考文献：
  名称：

  β-Biguanidinium-cyclodextrin: a supramolecular mimic of mitochondrial ADP/ATP carrier protein

  摘要：

  We reported a novel mono-beta-cyclodextrin derivative, mono-6-deoxy-6-biguanidino-beta-cyclodextrin (beta-biGCD), which was investigated as a mimic of ADP/ATP carrier (AAC). Its affinity toward AMP, ADP, and ATP was evaluated by means of isothermal titration calorimetry (ITC). The association constants (K-a) of beta-biGCD binding to AMP, ADP, and ATP were determined to be (1.07 +/- 0.04)x10(6), (5.86 +/- 0.02)x10(6), and (4.33 +/- 0.06)x10(6) L mo1(-1), respectively, which were 100-fold higher than mono-guanidino-beta-cyclodextrin (ca. 10(4) L mo1(-1)). UV spectroscopic titrations further confirmed the above results. The interaction between beta-biGCD and nucleotides was probed by docking simulation. These results reveal that the biguanidinium moiety mimics the arginine residues of mitochondrial AAC protein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.041

文献信息

• β-Biguanidinium-cyclodextrin: a supramolecular mimic of mitochondrial ADP/ATP carrier protein
  作者：Huo-Yan Chen、Meng Zhao、Jia-Heng Tan、Zhi-Shu Huang、Gao-Feng Liu、Liang-Nian Ji、Zong-Wan Mao

  DOI：10.1016/j.tet.2014.02.041

  日期：2014.4

  We reported a novel mono-beta-cyclodextrin derivative, mono-6-deoxy-6-biguanidino-beta-cyclodextrin (beta-biGCD), which was investigated as a mimic of ADP/ATP carrier (AAC). Its affinity toward AMP, ADP, and ATP was evaluated by means of isothermal titration calorimetry (ITC). The association constants (K-a) of beta-biGCD binding to AMP, ADP, and ATP were determined to be (1.07 +/- 0.04)x10(6), (5.86 +/- 0.02)x10(6), and (4.33 +/- 0.06)x10(6) L mo1(-1), respectively, which were 100-fold higher than mono-guanidino-beta-cyclodextrin (ca. 10(4) L mo1(-1)). UV spectroscopic titrations further confirmed the above results. The interaction between beta-biGCD and nucleotides was probed by docking simulation. These results reveal that the biguanidinium moiety mimics the arginine residues of mitochondrial AAC protein. (C) 2014 Elsevier Ltd. All rights reserved.