myo-Inositol 1,5,6-trisphosphate | 114488-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: myo-Inositol 1,5,6-trisphosphate
• 英文别名: D-myo-Inositol 1,5,6-triphosphate；D-myo-inositol 1,5,6-trisphosphate；myo-inositol 1,5,6-triphosphate；inositol 3,4,5-trisphosphate
• CAS: 114488-20-9
• 化学式: C₆H₁₅O₁₅P₃
• 分子量: 420.097
• InChiKey: GKDKOMAJZATYAY-XCMZKKERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.48
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  260.97
• 氢给体数：
  9.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  myo-Inositol 1,5,6-trisphosphate 在 3,4,5,6-tetrakisphosphate 1-kinase 作用下， 反应 0.05h， 生成 D-myo-inositol 1,4,5,6-tetrakisphosphate
  参考文献：
  名称：

  Regulation of ins(3456)p4 signalling by a reversible kinase phosphatase and methods and compositions related thereto

  摘要：

  提供了一种通过增加肌醇1,3,4,5,6五磷酸1-磷酸酶的活性来增加3,4,5,6-四磷酸的方法，以及通过降低肌醇1,3,4,5,6五磷酸1-磷酸酶的活性来降低3,4,5,6-四磷酸的方法。提供了一种减少主体中盐、液体或黏液分泌的方法，包括增加主体中肌醇1,3,4,5,6五磷酸1-磷酸酶的活性。还提供了一种治疗由盐、液体或黏液分泌加剧的疾病的方法，包括增加肌醇1,3,4,5,6五磷酸磷酸酶在患有由粘液加剧的疾病的主体中的活性，从而减少粘液分泌并治疗疾病。还提供了一种增加主体中盐和液体分泌的方法，包括降低主体中肌醇1,3,4,5,6五磷酸1-磷酸酶的活性。提供了一种治疗由增加盐和液体分泌而治疗的疾病的方法，包括降低肌醇1,3,4,5,6五磷酸1-磷酸酶在患有由增加盐和液体分泌而治疗的疾病的主体中的活性，从而增加盐和液体分泌并治疗疾病。

  公开号：

  US20060035810A1
• 作为产物：
  描述：

  (+/-)-(3/4,5,6)-4-bromo-5,6-epoxy-3-hydroxycyclohexene 在 四氮唑 、 ruthenium trichloride 、 lithium hydroxide 、 sodium periodate 、 硫酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 151.0h， 生成 myo-Inositol 1,5,6-trisphosphate
  参考文献：
  名称：

  肌醇磷酸的灵活立体和区域选择性合成（第2部分）：通过非对称的Conduritol B衍生物

  摘要：

  一种实用的路线的制备描述肌醇肌醇磷酸盐。可以通过对乙酰氨基乙酸二硬脂醇关键中间体的酶促拆分，从对苯醌制备两种形式的光学纯化合物。单取代的肌醇衍生物可通过破坏Conduritol B衍生物的C 2对称性而获得。各种各样的肌肌醇磷酸盐可以通过组合与这个新的非对称的方法先前报道的对称方法来合成。（©Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，Germany，2005）

  DOI：

  10.1002/ejoc.200400918

文献信息

• Synthesis of enantiomerically pure D-myo-inositol 1,5,6-triphosphate
  作者：Grzegorz M. Salamończyk、K.Michał Pietrusiewicz

  DOI：10.1016/s0040-4039(00)73160-1

  日期：1994.6

  The synthesis of enantiomerically pure D-myo-inositol 1,5,6-triphosphate from myo-inositol involving two sequential regioselective protections of hydroxyl groups in the intermediate selfresolving myo-inositol camphor monoacetal has been accomplished

  对映体纯D-的合成肌肉肌醇1,5,6三磷酸从肌醇肌醇涉及羟基的两个连续的区域选择性的保护在中间selfresolving肌醇肌醇樟脑单缩醛已经完成
• Enzyme-Assisted Total Synthesis of the Optical Antipodes <scp>d</scp>-<i>myo</i>-Inositol 3,4,5-Trisphosphate and <scp>d</scp>-<i>myo</i>-Inositol 1,5,6-Trisphosphate:  Aspects of Their Structure−Activity Relationship to Biologically Active Inositol Phosphates
  作者：Stephan Adelt、Oliver Plettenburg、Rolf Stricker、Georg Reiser、Hans-Josef Altenbach、Günter Vogel

  DOI：10.1021/jm981113k

  日期：1999.4.1

  Unambiguous total syntheses of bath optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P-3) and D-myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P-3) are described. The ring system characteristic of myo-inositol was constructed de novo from p-benzoquinone. X-ray data for the enzymatically resolved (1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene enabled the unequivocal assignment of the absolute configuration. Subsequent transformations under stereocontrolled conditions led to enantiopure C-2-symmetrical 1,4-(di-O-benzyldiphospho)conduritol B derivatives. Their synthetic potential was exploited to prepare Ins(3,4,5,6)P-4 and Ins(1,4,5,6)P-4 in three steps. With a recently identified and partially purified InsP(5)/InsP(4) phosphohydrolase from Dictyostelium discoideum, these enantiomers could be converted to the target compounds, Ins(3,4,5)P-3 and Ins(1,5,6)P-3, on a preparative scale. An HPLC system employed for both purification of the inositol phosphates and analytical runs ensured that the products were isomerically homogeneous. The sensitivity of detection achieved by a complexometric postcolumn derivatization method indicates that the complexation properties of Ins(3,4,5)P-3/Ins(1,5,6)P-3 resemble those of Ins(1,2,3)P-3, a compound with antioxidantpotential. The set of inositol phosphates synthesized was used to clarify structural motifs important for molecular recognition by p42(IP4) , high-affinity Ins(1,3,4,5)P-4/PtdIns(3,4,5)P-3-specific binding protein from pig cerebellum.
• Divergent Syntheses of All Possible Optically Active Regioisomers of <i>m</i><i>yo</i>-Inositol Tris- and Tetrakisphosphates
  作者：Sung-Kee Chung、Yong-Uk Kwon、Jung-Han Shin、Young-Tae Chang、Changgook Lee、Boo-Gyo Shin、Kyung-Cheol Kim、Mahn-Joo Kim

  DOI：10.1021/jo0257694

  日期：2002.8.1

  Since the discovery Of D-myo-inositol 1,4,5-trisphosphate, which plays a pivotal role as a second messenger in transmembrane signaling, the scope of the phosphoinositide-based signaling processes has been continually expanding. However, the clear understanding of the molecular signal transduction mechanisms including the functions of newly found IPn is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myoinositol phosphates (IPn; n = 1-6), we synthesized all possible optically active regioisomers of myo-IP3 and myo-IP4 using chiral IBz(3)s and IBz(2)s, respectively. A series of procedures involving CRL-catalyzed enzymatic resolution of racemic 1,2:5,6-di-O-isopropylidene-myo-inositoI and base-catalyzed benzoyl migration in tri- and dibenzoyl-isopropylidene-myo-inositol afforded eight enantiomeric pairs of IBz(3) and six enantiomeric pairs of IBz(2), respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.
• METHODS OF USING CYCLIC POLYANIONIC POLYOL DERIVATIVES FOR REGULATING SKIN WRINKLES
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0748210A1

  公开（公告）日：1996-12-18
• [EN] METHODS OF USING CYCLIC POLYANIONIC POLYOL DERIVATIVES FOR REGULATING SKIN WRINKLES<br/>[FR] PROCEDES FAISANT APPEL A DES DERIVES POLYANIONIQUES DE POLYOLS CYCLIQUES, POUR TRAITER LES RIDES DE LA PEAU
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：WO1995023588A1

  公开（公告）日：1995-09-08

  (EN) The subject invention relates to methods of regulating skin wrinkles and/or atrophy in mammalian skin comprising topically applying to the skin of a mammal in need of treatment a composition comprising a safe and effective amount of a cyclic polyanionic polyol derivative having structure (I) wherein n is an integer from 1 to 3; and each X is, independently, selected from the group consisting of OSO3-, OPO3=, SO3-, PO3=, CO2-, and OH; with at least 3 X's being other than OH.(FR) La présente invention concerne des procédés pour traiter les rides de la peau ou l'atrophie de la peau chez des mammifères, consistant à appliquer localement sur la peau d'un mammifère à traiter une composition contenant une quantité efficace mais sans danger d'un dérivé polyanionique d'un polyol cyclique ayant la structure (I). Dans cette structure, n est un nombre entier compris entre 1 et 3. Chaque X est choisi d'une manière indépendante, dans le groupe constitué par OSO3-, OPO3=, SO3-, PO3=, CO2- et OH. Au moins 3 X ne sont pas des OH.