Permethylated cycloinulohexaose | 148472-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Permethylated cycloinulohexaose
• 英文别名: permethylcycloinulohexaose
• CAS: 148472-81-5
• 化学式: C₅₄H₉₆O₃₀
• 分子量: 1225.34
• InChiKey: XQFNHNHCLAFGRA-MXWXUTMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.27
• 重原子数：
  84.0
• 可旋转键数：
  24.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  276.9
• 氢给体数：
  0.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  Permethylated cycloinulohexaose 在 甲酸 、 硼氘化钠 、 硫酸 作用下， 生成
  参考文献：
  名称：

  圆环芽孢杆菌OKUMZ 31B的胞外酶从菊粉中形成环寡糖

  摘要：

  从土壤中分离出的一种环状芽孢杆菌OKUMZ 31B菌株会产生一种细胞外酶，该酶可将菊粉转化为环鞘寡糖。主要产品被鉴定为环己基己糖。该酶被任意地命名为环脂寡糖果糖转移酶。

  DOI：

  10.1016/0008-6215(89)85167-5
• 作为产物：
  描述：

  (2R,3S,4S,5R,8R,10R,11S,12S,15R,17R,18S,19S,22R,24R,25S,26S,29R,31R,32S,33S,36R,38R,39S,40S)-2,10,17,24,31,38-六(羟甲基)-1,6,9,13,16,20,23,27,30,34,37,41-十二氧杂六螺[4.2.4~8~.2.4~15~.2.4~22~.2.4~29~.2.4~36~.2~5~]四十二烷-3,4,11,12 、 碘甲烷 在 dimethyl sulfoxide; deprotonated form 作用下， 以 二甲基亚砜 为溶剂， 生成 Permethylated cycloinulohexaose
  参考文献：
  名称：

  圆环芽孢杆菌OKUMZ 31B的胞外酶从菊粉中形成环寡糖

  摘要：

  从土壤中分离出的一种环状芽孢杆菌OKUMZ 31B菌株会产生一种细胞外酶，该酶可将菊粉转化为环鞘寡糖。主要产品被鉴定为环己基己糖。该酶被任意地命名为环脂寡糖果糖转移酶。

  DOI：

  10.1016/0008-6215(89)85167-5

文献信息

• Complexation characteristics of permethylated cycloinulohexaose, cycloinuloheptaose, and cycloinulooctaose with metal cations†
  作者：Motohiro Shizuma、Yoshio Takai、Mishio Kawamura、Tokuji Takeda、Masami Sawada

  DOI：10.1039/b102710g

  日期：——

  The host–guest complexation behavior of cyclic oligosaccharides, permethylated cycloinulohexaose 1, permethylated cycloinuloheptaose 2, and permethylated cycloinulooctaose 3 with metal cations has been characterized by means of UV-visible, NMR, and electrospray ionization (ESI) mass spectrometry. In the crystal state, the structures of 1·K+, 1·Rb+, and 1·Cs+ were same as that of the 1·Ba2+ complex which has a u-u-d-u-u-d (u = up, d = down) furanose ring arrangement for the plane of the crown ring moiety. The association constants (KS) in THF and in [2H6]acetone at 298 K were evaluated. The binding ability of host 1 with metal cations was of the same degree as that of calix[6]arene derivative 4 and much higher than those of hosts 2 and 3. The thermodynamic parameters of the complexation of host 1 with metal cation in THF were determined, and it was suggested that the entropy change for the solvation of the metal cations was one of the important factors in the complexation equilibrium. It was clarified that the structure of the host 1·K+ complex in solution at low temperature (furanose ring arrangement: u-d-u-d-u-d) was different from that in the crystal state (u-u-d-u-u-d arrangement) by the coalescence behavior in 1H-NMR. The relative peak intensity of the complex ions of host 1 or 2 with two alkali metal ions in ESI mass spectrometry (in acetone) showed a correlation in the first order approximation with the ratio of the corresponding complex ion concentrations estimated from the KS values.

  环状低聚糖与金属离子的主客体络合行为，即全甲基化环状菊粉六聚糖1、全甲基化环状菊粉七聚糖2和全甲基化环状菊粉八聚糖3，已通过紫外-可见光谱、核磁共振和电喷雾电离（ESI）质谱法进行了表征。在晶体状态下，1·K+、1·Rb+和1·Cs+的结构与1·Ba2+络合物的结构相同，其中皇冠环部分平面的呋喃糖环排列为u-u-d-u-u-d（u=向上，d=向下）。在298 K下，THF和[2H6]丙酮中的结合常数（KS）得到了评估。宿主1与金属离子的结合能力与杯[6]芳烃衍生物4相当，远高于宿主2和3。确定了宿主1与金属离子在THF中的络合作用的热力学参数，并提出金属离子的溶剂化熵变是络合平衡中的重要因素之一。通过1H-NMR中的合并行为，明确了在低温溶液中宿主1·K+络合物的结构（呋喃糖环排列：u-d-u-d-u-d）与晶体状态下的结构（u-u-d-u-u-d排列）不同。在ESI质谱法（在丙酮中）中，宿主1或2与两种碱金属离子的络合离子相对峰强度与根据KS值估计的相应络合离子浓度比在第一近似中呈相关性。
• [EN] COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR DES CYCLOFRUCTANES EN TANT QU'AGENTS DE SÉPARATION
  申请人：UNIV TEXAS

  公开号：WO2010148191A3

  公开（公告）日：2011-05-19
• Binding Characteristics of a New Host Family of Cyclic Oligosaccharides from Inulin: Permethylated Cycloinulohexoase and Cycloinuloheptaose
  作者：Yoshio Takai、Yasuo Okumura、Takanori Tanaka、Masami Sawada、Shigetoshi Takahashi、Motoo Shiro、Mishio Kawamura、Takao Uchiyama

  DOI：10.1021/jo00090a013

  日期：1994.6

  The complexation behavior of a new class of cyclic oligosaccharide hosts, permethylated cycloinulohexaose 1b and permethylated cycloinuloheptaose 2b, with various metallic cation guests has been characterized by means of FAB mass and NMR spectrometry and X-ray crystallography. A series of association constants (K-s) with metallic cations in acetone (Li+ < Na+ < Cs+ < K+ < Ba2+ showed that 1b acts like an 18-crown-6 derivative, but the binding abilities are lower by a factor of roughly 10(2) in the magnitude of K-s when compared with 18-crown-6 itself. Coupled with kinetic data (k(-1)), charge-induced shift data, and low-temperature NMR signal splittings, as well as its cation selectivity pattern, the structure of the complex in solution was deduced such that the metallic cation is not captured by the central hole of the 18-crown-6 moiety of 1b but is in the pocket constructed both by the upper rim OMe-3 oxygens of the furanose rings and by the crown ether oxygens. Unequivocal evidence for the OMe-3 participation in the cation binding of 1b has been presented based on the crystalline structure of its barium cation complex [1b.Ba2+].