D-1-O-allyl-3,4,5,6-tetra-O-benzyl-myo-inositol | 64681-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: D-1-O-allyl-3,4,5,6-tetra-O-benzyl-myo-inositol
• 英文别名: (1S,2S,3R,4R,5S,6R)-2,3,4,5-tetrakis(phenylmethoxy)-6-prop-2-enoxycyclohexan-1-ol
• CAS: 64681-28-3
• 化学式: C₃₇H₄₀O₆
• 分子量: 580.721
• InChiKey: USTYCLMGJFBSMX-APGXMLRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-1-O-allyl-3,4,5,6-tetra-O-benzyl-myo-inositol 在 三乙烯二胺 、 四氮唑 、 Wilkinson's catalyst 、 水 、 sodium hydride 、 sulfur 、 溶剂黄146 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.75h， 生成 (+)-2,3,4,5,6-pentakis-O-benzyl myo-inositol bis(2-cyanoethyl) phosphorothioate
  参考文献：
  名称：

  d-和1-肌醇肌醇-1-磷酸酯，为肌醇单磷酸酶底物

  摘要：

  D-和L-的对映异构体肌醇肌醇-1-磷酸酯已经从2,3,4,5,6-胺五-O-苄合成肌醇肌醇在6个步骤，这两种化合物是用于肌醇单磷酸酶的底物。在L-肌-肌醇1-硫代磷酸酯的替代合成中，D-吡喃葡萄糖6-磷酸硫代磷酸酯不作为酶肌醇合酶的底物。

  DOI：

  10.1016/s0040-4020(01)80912-1
• 作为产物：
  描述：

  1-O-allyl-3,4,5,6-tetra-O-benzyl-2-O-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol 在 盐酸 、 溶剂黄146 作用下， 反应 3.0h， 生成 D-1-O-allyl-3,4,5,6-tetra-O-benzyl-myo-inositol
  参考文献：
  名称：

  Synthesis of 1-O-(1,2-Di-O-palmitoyl-SN-glycero-3-phosphoryl)-2-O-α-D-mannopyranosyl-D-MYO-inositol: a fragment of mycobacterial phospholipids

  摘要：

  DOI：

  10.1016/s0040-4020(01)81026-7

文献信息

• Inositol polyphosphates and methods of using same
  申请人：The Regents of the University of California

  公开号：US05880099A1

  公开（公告）日：1999-03-09

  The present invention provides compositions that are cell permeable antagonists of inositol polyphosphates. In addition, the invention provides methods for enhancing chloride ion secretion from a cell by contacting the cells with cell permeable antagonists of inositol polyphosphates. The invention also provides methods for enhancing chloride ion secretion in an individual by administering cell permeable antagonists of inositol polyphosphates to the individual. The invention additionally provides methods for alleviating a sign or symptom associated with cystic fibrosis in an individual by administering a cell permeable antagonist of inositol polyphosphates to the individual. The invention also provides compositions that are cell permeable agonists of inositol polyphosphates. In addition, the invention provides methods for decreasing chloride ion secretion from a cell by contacting the cell with cell permeable agonists of inositol polyphosphates. The invention also provides methods for decreasing chloride ion secretion in an individual by administering cell permeable agonists of inositol polyphosphates to the individual. The invention additionally provides methods for alleviating a sign or symptom associated with secretory diarrhea in an individual by administering cell permeable agonists of inositol polyphosphates to the individual.

  本发明提供了一种可透过细胞的肌醇多磷酸拮抗剂。此外，本发明还提供了一种通过将细胞与肌醇多磷酸的细胞可透过拮抗剂接触来增强细胞分泌氯离子的方法。本发明还提供了一种通过向个体施用肌醇多磷酸的细胞可透过拮抗剂来增强个体中氯离子分泌的方法。本发明还进一步提供了一种通过向个体施用肌醇多磷酸的细胞可透过拮抗剂来缓解与囊性纤维化相关的体征或症状的方法。本发明还提供了一种肌醇多磷酸的细胞可透过激动剂。此外，本发明还提供了一种通过将细胞与肌醇多磷酸的细胞可透过激动剂接触来减少细胞分泌氯离子的方法。本发明还提供了一种通过向个体施用肌醇多磷酸的细胞可透过激动剂来减少个体中氯离子分泌的方法。本发明还进一步提供了一种通过向个体施用肌醇多磷酸的细胞可透过激动剂来缓解与分泌性腹泻相关的体征或症状的方法。
• The absolute configuration of (+)-1,2,4,5,6-penta-O-benzyl-myo-inositol
  作者：R. Aneja、S. Aneja、V.P. Pathak、P.T. Ivanova

  DOI：10.1016/0040-4039(94)88075-1

  日期：1994.8

  The absolute configuration of (+)-1,2,4,5,6-penta-O-benzyl-myo-inositol is correlated with 1D-1,4,5,6-tetra-O-benzyl-myo-inositol and thus confirmed as 1D-1,2,4,5,6-penta-O-benzyl-myo-inositol.

  的绝对构型（+） - 1,2,4,5,6-五ö苄基肌-肌醇是相关与1D-1,4,5,6-四ö苄基肌-肌醇和因此确认为1D-1,2,4,5,6-五ö苄基肌-肌醇。
• New fluorescent probes reveal that flippase-mediated flip-flop of phosphatidylinositol across the endoplasmic reticulum membrane does not depend on the stereochemistry of the lipid
  作者：Ram A. Vishwakarma、Stefanie Vehring、Anuradha Mehta、Archana Sinha、Thomas Pomorski、Andreas Herrmann、Anant K. Menon

  DOI：10.1039/b500300h

  日期：——

  Glycerophospholipid flip-flop across biogenic membranes such as the endoplasmic reticulum (ER) is a fundamental feature of membrane biogenesis. Flip-flop requires the activity of specific membrane proteins called flippases. These proteins have yet to be identified in biogenic membranes and the molecular basis of their action is unknown. It is generally believed that flippase-facilitated glycerophospholipid flip-flop across the ER is governed by the stereochemistry of the glycerolipid, but this important issue has not been resolved. Here we investigate whether the ER flippase stereochemically recognizes the glycerophospholipids that it transports. To address this question we selected phosphatidylinositol (PI), a biologically important molecule with chiral centres in both its myo-inositol headgroup and its glycerol–lipid tail. The flip-flop of PI across the ER has not been previously reported. We synthesized fluorescence-labeled forms of all four diastereoisomers of PI and evaluated their flipping in rat liver ER vesicles, as well as in flippase-containing proteoliposomes reconstituted from a detergent extract of ER. Our results show that the flippase is able to translocate all four PI isomers and that both glycerol isomers of PI flip-flop across the ER membrane at rates similar to that measured for fluorescence-labeled phosphatidylcholine. Our data have important implications for recent hypotheses concerning the evolution of distinct homochiral glycerophospholipid membranes during the speciation of archaea and bacteria/eukarya from a common cellular ancestor.

  甘油磷脂在生物膜（如内质网）上的翻转是膜生物发生的一个基本特征。翻转需要特定膜蛋白（即翻转酶）的活性，但这些蛋白质在生物膜中的身份尚未确定，其作用的分子基础也还不清楚。一般认为，内质网上的翻转酶介导的甘油磷脂翻转受甘油磷脂的手性化学支配，但这一重要问题尚未解决。在此，我们研究内质网翻转酶是否手性识别其转运的甘油磷脂。为解答这一问题，我们选择了磷脂酰肌醇，这种生物学上重要的分子在其肌醇头基和甘油脂尾上都具有手性中心。之前并未有过关于磷脂酰肌醇在内质网翻转的报道。我们合成了所有四种磷脂酰肌醇的非对映异构体并进行荧光标记，评估它们在大鼠肝脏内质网囊泡及从内质网洗涤剂提取物重建的含翻转酶的蛋白脂质体中的翻转情况。结果显示，翻转酶能够转运所有的磷脂酰肌醇异构体，两种磷脂酰肌醇的甘油异构体在内质网膜上的翻转速率与荧光标记的磷脂酰胆碱相当。这些数据对近期有关古菌和细菌/真核生物从共同的细胞祖先演化出不同手性的甘油磷脂膜的假设有着重要意义。
• Syntheses of Penta-<b><i>O</i></b>-benzyl-<b><i>myo</i></b>-inositols,<b><i>O</i></b>-<b><i>β</i></b>-<b>L</b>-Arabinosyl-(1 → 2)-<b><i>sn</i></b>-<b><i>myo</i></b>-inositol,<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-Galactosyl-(1 → 3)-<b><i>sn</i></b>-<b><i>myo</i></b>-inositol, and<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-Galactosyl-(1 → 6)-<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-galactosyl-(1 → 3)-<b><i>sn</i></b>-<b><i>myo</i></b>-inositol
  作者：Shinkiti Koto、Motoko Hirooka、Toyosaku Yoshida、Kazuhiro Takenaka、Chizuru Asai、Toshiki Nagamitsu、Hiroaki Sakuma、Michiyo Sakurai、Shinichi Masuzawa、Mitsuo Komiya、Tadaaki Sato、Shonosuke Zen、Kazuo Yago、Fumiya Tomonaga

  DOI：10.1246/bcsj.73.2521

  日期：2000.11

  Two-step conversions of myo-inositol into (±)-2,3,4,5,6- and 1,3,4,5,6-penta-O-benzyl-myo-inositols are described. Starting from these monohydroxy derivatives of myo-inositol, O-β-L-arabinopyranosyl-(1 → 2)-sn-myo-inositol from Japanese green tea [SENCHA], Camellia sinensis, and O-α-D-galactopyranosyl-(1 → 3)-sn-myo-inositol (galactinol) as well as its homolog, O-α-D-galactopyranosyl-(1 → 6II)-galactinol, were synthesized by way of the in situ activating glycosylation procedure.

  本文描述了肌醇向（±）-2,3,4,5,6-和1,3,4,5,6-五-O-苄基-肌醇的两步转化过程。从这些单羟基衍生的肌醇出发，通过原位活化糖基化程序合成了来自日本绿茶（煎茶，山茶属）的O-β-L-阿拉伯呋喃糖基-（1→2）-sn-肌醇和O-α-D-半乳吡喃糖基-（1→3）-sn-肌醇（半乳糖醇）及其同系物，O-α-D-半乳吡喃糖基-（1→6II）-半乳糖醇。
• Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation
  作者：Subramanian Devaraj、Rajendra C. Jagdhane、Mysore S. Shashidhar

  DOI：10.1016/j.carres.2009.04.007

  日期：2009.7

  one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results

  含有一个以上羟基的肌醇衍生物经由其碱金属醇盐（钠或锂）的O-烷基化优先发生在具有邻位顺式氧原子的羟基上。通常，观察到的对于烷氧基锂的选择性比对相应的烷氧基钠的选择性更高。观察到的区域选择性还取决于其他因素，例如溶剂和反应温度。对本文提供的结果以及文献中提供的结果的仔细研究表明，肌醇衍生物对金属离子的螯合在观察到的区域选择性中起着重要作用。与反应的羟基的轴向或赤道位置有关的立体因素对这些O-烷基化反应的结果没有太大贡献。