(+/-)-myo-inositol 1,2,3,6-tetrakisphosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-myo-inositol 1,2,3,6-tetrakisphosphate
• 英文别名: [(1R,2S,3S,4R,5S,6R)-2,3-dihydroxy-4,5,6-triphosphonooxycyclohexyl] dihydrogen phosphate
• 化学式: C₆H₁₆O₁₈P₄
• 分子量: 500.077
• InChiKey: MRVYFOANPDTYBY-FTYOSCRSSA-N

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

反应信息

• 作为反应物：
  描述：

  (+/-)-myo-inositol 1,2,3,6-tetrakisphosphate 在 Dictyostelium phytase 作用下， 以 水 为溶剂， 以100%的产率得到D-myo-inositol 2,3,6-trisphosphate
  参考文献：
  名称：

  De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4—regiospecificity of their enzymatic dephosphorylation

  摘要：

  (T)he first total synthesis of Ins(1,2,3,4)P-4 and Ins(1,2,3,6)P-4 is presented. Starting from p-benzoquinone, we took advantage of the C-2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP(3) isomers, were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P-3, Ins(2,3,6)P-3 and Ins(1,2,4)P-3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00063-x
• 作为产物：
  描述：

  (+)-(1R,2S,3S,4R)-2,3-dibromocyclohex-5-ene-1,4-diol 在 palladium on activated charcoal 吡啶 、 四氮唑 、 ruthenium trichloride 、 氢氧化钾 、 sodium hydroxide 、 sodium periodate 、 氢气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 生成 (+/-)-myo-inositol 1,2,3,6-tetrakisphosphate
  参考文献：
  名称：

  De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4—regiospecificity of their enzymatic dephosphorylation

  摘要：

  (T)he first total synthesis of Ins(1,2,3,4)P-4 and Ins(1,2,3,6)P-4 is presented. Starting from p-benzoquinone, we took advantage of the C-2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP(3) isomers, were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P-3, Ins(2,3,6)P-3 and Ins(1,2,4)P-3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00063-x

文献信息

• Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates(Part 1): Via Symmetrical Conduritol B Derivatives
  作者：Michael A. L. Podeschwa、Oliver Plettenburg、Hans-Josef Altenbach

  DOI：10.1002/ejoc.200400911

  日期：2005.7

  myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivatives can be obtained by breaking the C2 symmetry of conduritol B derivatives. A wide variety of myo-inositol phosphates can be synthesized by combining the previously reported symmetrical approach with

  描述了用于制备肌醇磷酸酯的实用路线。通过酶促拆分二乙酰氧基硬糖醇关键中间体，可以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以通过破坏 conduritol B 衍生物的 C2 对称性来获得。通过将先前报道的对称方法与这种新的非对称方法相结合，可以合成多种肌醇磷酸酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• [EN] SYNTHESIS OF CYCLOHEXANE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS<br/>[FR] SYNTHÈSE DE DÉRIVÉS DE CYCLOHEXANE UTILES COMME AGENTS SENSORIELS DANS DES PRODUITS DE CONSOMMATION
  申请人：PROCTER & GAMBLE

  公开号：WO2010019730A1

  公开（公告）日：2010-02-18

  The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

  本发明提供了合成路径，用于制备基于环己烷的各种异构体冷却剂，例如薄荷酯和薄荷烷甲酰衍生物，特别是那些在酰胺氮上取代的，例如带有芳香环或芳基的。这些结构具有高冷却效能和持久的感官效果，使它们在各种消费品中有用。一种合成路径涉及使用铜催化剂将一种初级薄荷烷甲酰胺与芳香卤代烃偶联，这种反应在存在磷酸钾和水的情况下效果最佳。利用这种合成路径，可以制备特定的异构体，包括具有与l-薄荷醇相同构型的薄荷烷甲酰胺异构体以及具有在羧酰胺（C-1）位置上相反立体化学的新异构体，该新异构体意外地具有强效和持久的冷却效果。还提供了其他薄荷衍生物的新异构体的制备方案，这些衍生物包括酯类、醚类、羧酯类和其他N-取代羧酰胺，它们也可用作冷却剂。
• Quantitative Analysis of Phytate Globoids Isolated from Wheat Bran and Characterization of Their Sequential Dephosphorylation by Wheat Phytase
  作者：Lisbeth Bohn、Lone Josefsen、Anne S. Meyer、Søren K. Rasmussen

  DOI：10.1021/jf071191t

  日期：2007.9.1

  when pure phytic acid was replaced with phytate globoids as substrate. Time course degradation of phytic acid or phytate globoids using purified wheat phytase was followed by HPIC identification of inositol phosphates appearing and disappearing as products. In both cases, enzymatic degradation initiated at both the 3- and 6-positions of phytic acid and end products were inositol and phosphate.

  纯化了小麦植酸酶，以研究该酶对其纯底物（植酸-肌醇六磷酸）和其天然底物（植酸球状）的作用。从麦麸中纯化植酸球蛋白至均质，并通过ICP-MS定量其营养相关参数。球形物质的主要成分是植酸（40％w / w），蛋白质（46％w / w）和几种矿物质，特别是K> Mg> Ca> Fe（按浓度顺序）。酶动力学研究表明，当纯植酸被植酸球体替代时，K（m）和V（max）分别降低29％和37％。使用纯化的小麦肌醇六磷酸酶随时间推移降解肌醇六磷酸或肌醇六磷酸球，然后通过HPIC鉴定肌醇磷酸酯作为产物的出现和消失。在这两种情况下，在植酸的3位和6位上开始的酶促降解以及最终产物是肌醇和磷酸盐。
• Regulation of ins(3456)p4 signalling by a reversible kinase phosphatase and methods and compositions related thereto
  申请人：Shears B Stephen

  公开号：US20060035810A1

  公开（公告）日：2006-02-16

  Provided is a method of increasing 3,4,5,6-tetrakisphosphate by increasing the activity of inositol 1,3,4,5,6 pentakisphosphate 1-phosphatase, and a method of decreasing 3,4,5,6-tetrakisphosphate by decreasing the activity of inositol 1,3,4,5,6 pentakisphosphate 1-phosphatase. A method of reducing salt, fluid or mucous secretion in a subject, comprising increasing the activity of inositol 1,3,4,5,6 pentakisphosphate 1-phosphatase in the subject is provided. A method of treating a disease that is exacerbated by salt, fluid or mucous secretion is also provided, comprising increasing the activity of inositol 1,3,4,5,6 pentakisphosphate phosphatase in a subject having a disease that is exacerbated by mucous, whereby mucous secretion is reduced and the disease is treated. Also provided is method of increasing salt and fluid secretion in a subject, comprising decreasing the activity of inositol 1,3,4,5,6 pentakisphosphate 1-phosphatase in the subject. A method of treating a disease that is treated by increased salt and fluid secretion is provided, comprising decreasing the activity of inositol 1,3,4,5,6 pentakisphosphate 1-phosphatase in a subject having a disease that is treated by increased salt and fluid secretion, whereby salt and fluid secretion is increased and the disease is treated.

  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3,4,5,6四磷酸盐的方法，以及通过降低肌醇1,3,4,5,6五磷酸1-磷酸酶的活性来减少3,4,5,6四磷酸盐的方法。提供了一种在受试对象中减少盐、液体或黏液分泌的方法，包括增加受试对象中肌醇1,3,4,5,6五磷酸1-磷酸酶的活性。还提供了一种治疗因盐、液体或黏液分泌加重的疾病的方法，包括增加患有因黏液分泌加重的疾病的受试对象中肌醇1,3,4,5,6五磷酸磷酸酶的活性，从而减少黏液分泌并治疗疾病。还提供了一种在受试对象中增加盐和液体分泌的方法，包括降低受试对象中肌醇1,3,4,5,6五磷酸1-磷酸酶的活性。提供了一种治疗因增加盐和液体分泌而治疗的疾病的方法，包括降低因增加盐和液体分泌而治疗的疾病的受试对象中肌醇1,3,4,5,6五磷酸1-磷酸酶的活性，从而增加盐和液体分泌并治疗疾病。
• Synthesis of Cyclohexane Derivatives Useful as Sensates in Consumer Products
  申请人：Yelm Kenneth Edward

  公开号：US20100076080A1

  公开（公告）日：2010-03-25

  The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

  本发明提供了合成环己基冷却剂的各种异构体的合成路线，例如酯类薄荷醇和酰胺衍生物，特别是那些在酰胺氮上被取代的，例如芳香环或芳基基团。这样的结构具有高冷却效能和持久的感官效应，使它们在各种消费品中有用。一种合成路线涉及一种铜催化的一次性薄荷醇酰胺与芳基卤化物的偶联反应，这种反应在存在磷酸钾和水的情况下效果最好。使用这种合成路线，可以制备特定的异构体，包括具有与l-薄荷醇相同构型的薄荷醇酰胺异构体和新的异构体，例如在羧酰胺（C-1）位置具有相反立体化学的新异构体。这种新异构体出人意料地具有强大而持久的冷却效果。还提供了其他薄荷醇衍生物的新异构体的制备方案，这些衍生物包括酯类、醚类、羧酸酯类和其他N-取代酰胺。