[(1R,2S,3S,4R,5S,6R)-3,4-二羟基-2,5,6-三膦酰氧基环己基]磷酸二氢酯 | 112791-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [(1R,2S,3S,4R,5S,6R)-3,4-二羟基-2,5,6-三膦酰氧基环己基]磷酸二氢酯
• 中文别名: 纤维醇-3,4,5,6-四磷酸酯
• 英文名称: D-myo-inositol 3,4,5,6-tetrakisphosphate
• 英文别名: inositol 1,4,5,6-tetrakisphosphate；[3H]-Inositol-3,4,5,6-tetrakisphosphate；[(1S,2R,3S,4S,5R,6R)-2,3-dihydroxy-4,5,6-triphosphonooxycyclohexyl] dihydrogen phosphate
• CAS: 112791-61-4；121010-58-0
• 化学式: C₆H₁₆O₁₈P₄
• 分子量: 500.077
• InChiKey: MRVYFOANPDTYBY-UZAAGFTCSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -8.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  308
• 氢给体数：
  10
• 氢受体数：
  18

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Inositol 1,3,4,5-tetrakisphosphate	102850-29-3	C6H16O18P4	500.08

反应信息

• 作为反应物：
  描述：

  [(1R,2S,3S,4R,5S,6R)-3,4-二羟基-2,5,6-三膦酰氧基环己基]磷酸二氢酯 在 Arabidopsis thaliana inositol 1,3,4,5,6-pentakisphosphate 2-kinase 、 5’-三磷酸腺苷 、 sodium chloride 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 0.5h， 生成 D-myo-inositol 2,3,4,5,6-pentakisphosphate
  参考文献：
  名称：

  Roles of Phosphate Recognition in Inositol 1,3,4,5,6-Pentakisphosphate 2-Kinase (IPK1) Substrate Binding and Activation

  摘要：

  Inositol phosphate kinases (IPKs) sequentially phosphorylate inositol phosphates (IPs) to yield a group of small signaling molecules involved in diverse cellular processes. IPK1(inositol 1,3,4,5,6-pentakisphosphate 2-kinase) phosphorylates inositol 1,3,4,5,6-pentakisphosphate to inositol 1,2,3,4,5,6-hexakisphosphate; however, the mechanism of IP recognition employed by IPK1 is currently unresolved. We demonstrated previously that IPK1 possesses an unstable N-terminal lobe in the absence of IP, which led us to propose that the phosphate profile of the IP was linked to stabilization of IPK1. Here, we describe a systematic study to determine the roles of the 1-, 3-, 5-, and 6-phosphate groups of inositol 1,3,4,5,6-pentakisphosphate in IP binding and IPK1 activation. The 5- and 6-phosphate groups were the most important for IP binding to IPK1, and the 1- and 3-phosphate groups were more important for IPK1 activation than the others. Moreover, we demonstrate that there are three critical residues (Arg-130, Lys-170, and Lys-411) necessary for IPK1 activity. Arg-130 is the only substrate-binding N-terminal lobe residue that can render IPK1 inactive; its 1-phosphate is critical for full IPK1 activity and for stabilization of the active conformation of IPK1. Taken together, our results support the model for recognition of the IP substrate by IPK1 in which (i) the 4-, 5-, and 6-phosphates are initially recognized by the C-terminal lobe, and subsequently, (ii) the interaction between the 1-phosphate and Arg-130 stabilizes the N-terminal lobe and activates IPK1. This model of IP recognition, believed to be unique among IPKs, could be exploited for selective inhibition of IPK1 in future studies that investigate the role of higher IPs.

  DOI：

  10.1074/jbc.m113.487777
• 作为产物：
  描述：

  Inositol 在 palladium on activated charcoal 四氮唑 、 硫酸 、 氢气 、 对甲苯磺酸 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 反应 27.33h， 生成 [(1R,2S,3S,4R,5S,6R)-3,4-二羟基-2,5,6-三膦酰氧基环己基]磷酸二氢酯
  参考文献：
  名称：

  由肌醇合成手性磷酸肌醇

  摘要：

  高效转换的一个新的合成方法肌醇肌醇成纯手性肌醇磷酸被呈现，并且与全合成所示肌醇-1-磷酸，2-脱氧肌醇-1-磷酸，肌醇肌醇-3-磷酸，肌肌醇-4-磷酸，肌醇肌醇1,4-二磷酸，肌醇肌醇1,4,5-三磷酸和肌醇肌醇3,4,5,6-四磷酸盐。该合成开始selfresolving肌肌醇camphanylidene顺-monoacetals 2A和2A'分别从母体环糖醇和D-和L-樟脑二甲基缩醛一步获得，并通过沉淀驱动的平衡方便地收获。合成的关键步骤是2a和2a'的选择性单磷酸化，选择性双甲硅烷基化和选择性三酰基化，以及使用二氯磷酸二苄酯和2-二甲氨基-5,6-苯并-1,3,2-二氧杂磷杂环戊烷来实现单磷酸化和多磷酸化。为了支持立体化学分配，还提出了一种中间体完全保护的肌醇衍生物之一的X射线结构。

  DOI：

  10.1016/s0040-4020(01)88305-8
• 作为试剂：
  描述：

  二氧化碳 、 calcium hydroxide 在 [(1R,2S,3S,4R,5S,6R)-3,4-二羟基-2,5,6-三膦酰氧基环己基]磷酸二氢酯 作用下， 以 水 为溶剂， 反应 0.01h， 生成 calcium carbonate
  参考文献：
  名称：

  Inositol tetrakisphosphate from chicken eggshell

  摘要：

  Unlike our previous study that identified D-myo-inositol 4,5-bisphosphate (Ins(4,5)P-2, 1) from ostrich eggshell, the compound myo-inositol 1,4,5,6-tetrakisphosphate (Ins(1,4,5,6)P-4, 2) was isolated as an almost racemic mixture from the internal region of chicken eggshell. Furthermore, 2, 2-[H-2]-2, and amorphous CaCO3 were prepared as tools for assessment about transformation of CaCO3 during bone formation. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2019.130853

文献信息

• Inositol derivatives for increasing chloride secretion and inhibiting inflammation
  申请人：——

  公开号：US20040147487A1

  公开（公告）日：2004-07-29

  Inositol derivatives, compositions comprising inositol derivatives, and methods for using compositions comprising inositol derivatives as agents for activating the secretion of chloride ions and/or treatment of inflammation are described.

  肌醇衍生物、包含肌醇衍生物的组成物以及使用包含肌醇衍生物的组成物作为激活氯离子分泌和/或治疗炎症的剂的方法被描述。
• Membrane-permeant analogues of the putative second messenger myo-inositol 3,4,5,6-tetrakisphosphate
  作者：Stefan Roemer、Christoph Stadler、Marco T. Rudolf、Bernd Jastorff、Carsten Schultz

  DOI：10.1039/p19960001683

  日期：——

  investigations of the binding properties of D-myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate [D-Ins(3,4,5,6)P4 and D-Ins(1,4,5,6)P4, respectively] to their putative target proteins, a set of analogues with modifications of the 1(3)- and/or 2-hydroxy group has been prepared. The reaction sequences started from D-3,4,5,6-tetra-O-benzyl-myo-inositol or its D-1,4,5,6-enantiomer, respectively and allowed

  为的结合性质的将来的调查d -肌醇肌醇3,4,5,6-和1,4,5,6-四磷酸盐[ d -INS（3,4,5,6-）P 4和d -INS （1,4,5,6）P 4分别对它们的推定靶蛋白制备了一组具有1（3）-和/或2-羟基修饰的类似物。从开始的反应顺序d -3,4,5,6-四ö苄基肌-肌醇或它的d-1,4,5,6-对映体，并允许引入具有退化性氢键的基团，例如甲氧基或氯，取代羟基。另外，相应的DL -鲨肌醇的前体24的制备是通过使用一个共同的亚磷酸酯的方法2-肌糖衍生物23.古典保护/去保护化学和随后的磷酸化立体化学优化还原，得到四磷酸盐类似物1A-E，3。这些衍生物被转化为不带电荷的可生物活化的乙酰氧基甲基酯2a–e，4。为避免乙酰氧基甲基烷基化过程中磷酸盐环化，并增加潜在的膜渗透性Ins P 4的亲脂性 单取代的四磷酸酯的衍生物的羟基被细胞内可水解的丁酸酯覆盖。
• Synthesis of D-myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate analogues and their membrane-permeant derivatives
  作者：Stefan Roemer、Marco T. Rudolf、Christoph Stadler、Carsten Schultz

  DOI：10.1039/c39950000411

  日期：——

  A set of D-myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphates [D-Ins(3,4,5,6)P4 and D-Ins(1,4,5,6)P4, respectively] analogues with modifications of the hydroxy groups is synthesized and subsequently converted to the corresponding uncharged, bioactivatable acetoxymethyl esters.

  一系列D-肌醇3,4,5,6-和1,4,5,6-四磷酸盐[分别为D-Ins(3,4,5,6)P4和D-Ins(1,4,5,6)P4]类似物，其羟基进行了修饰，被合成并随后转化为相应的无电荷、生物活性可激活的乙酰氧甲基酯。
• A Definitive Synthesis ofD-myo-Inositol 1,4,5,6-Tetrakisphosphate and Its EnantiomerD-myo-Inositol 3,4,5,6-Tetrakisphosphate from a Novel Butane-2,3-diacetal-Protected Inositol
  作者：Stephen J. Mills、Andrew M. Riley、Changsheng Liu、Mary F. Mahon、Barry V. L. Potter

  DOI：10.1002/chem.200305207

  日期：2003.12.15

  rapid syntheses of the enantiomeric intracellular signalling molecules d-myo-inositol 1,4,5,6-tetrakisphosphate (1 a) and D-myo-inositol 3,4,5,6-tetrakisphosphate (1 b) are described. The synthetic strategy employs the novel butane-2,3-diacetal-protected (BDA-protected) myo-inositol (+/-)-3 ab, directly accessible from myo-inositol on a large scale, and an optical resolution with diastereoisomeric (R

  描述了对映体细胞内信号分子d-肌醇1,4,5,6-四磷酸（1a）和D-肌醇3,4,5,6-四磷酸（1b）的快速合成。合成策略采用新型的丁烷2,3-二缩醛保护的（BDA保护的）肌醇（+/-）-3 ab，可直接从肌醇直接大规模获得，并具有非对映异构体（ R）-（-）-乙酰扁桃酸酯。还展示了（+/-）-4的X射线晶体结构，这是肌醇与丁二酮发生酸催化反应的不寻常副产物，并且通过转化成1a和1b的绝对构型来确定其绝对构型。关键的前体分别为（+）-冰片糖醇和L-艾杜糖醇六乙酸酯。与天然多磷酸盐相比，证实了合成物1b的生物活性。
• [EN] L-CARNITINE AND ALKANOYL L-CARNITINE PHYTATES AND PROCESS FOR PREPARING THE SAME<br/>[FR] PHYTATES DE L-CARNITINE ET D'ALCANOYLE L-CARNITINE, ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：SCIAN LAB LLC

  公开号：WO2010005465A1

  公开（公告）日：2010-01-14

  Salts of L-carnitine and alkanoyl L-carnitines with phytic acid of general formula (I), and the process of preparing the same, wherein the mole ratio between the L-carnitine or its alkanoyl derivatives cation and phytic acid anion be within the range of 1 :1 to 6:1, wherein: n = 1-6; R1 is the phytate anion; R is either hydrogen, a straight alkanoyl group having 2-12 carbon atoms or a branched-chain alkanoyl group having 2-12 carbon atoms.

  L-肉碱盐和烷酰基L-肉碱盐与一般公式(I)的植酸，以及制备这些化合物的过程，其中L-肉碱或其烷酰衍生物阳离子与植酸阴离子之间的摩尔比在1:1至6:1的范围内，其中：n = 1-6；R1为植酸阴离子；R为氢、具有2-12个碳原子的直链烷酰基团或具有2-12个碳原子的支链烷酰基团。