(3aS,4R,5S,6S,7R,7aR)-2,5,6,7-四羟基-2-氧代六氢-1,3,2-苯并二氧磷杂戊环-4-基 2-氨基-2-脱氧-alpha-D-吡喃葡萄糖苷 | 140391-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3aS,4R,5S,6S,7R,7aR)-2,5,6,7-四羟基-2-氧代六氢-1,3,2-苯并二氧磷杂戊环-4-基 2-氨基-2-脱氧-alpha-D-吡喃葡萄糖苷
• 中文别名: (3aS,4R,5S,6S,7R,7aR)-2,5,6,7-四羟基-2-氧代六氢-1,3,2-苯并二氧磷杂戊环-4-基2-氨基-2-脱氧-alpha-D-吡喃葡萄糖苷
• 英文名称: 6-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1,2-(Cyclic)phosphate
• 英文别名: (3aS,4R,5S,6S,7R,7aR)-4-[(2-azaniumyl-2-deoxy-alpha-D-glucopyranosyl)oxy]-5,6,7-trihydroxyhexahydro-1,3,2-benzodioxaphosphol-2-olate 2-oxide；[(2R,3R,4R,5S,6R)-2-[[(3aS,4R,5S,6S,7R,7aR)-5,6,7-trihydroxy-2-oxido-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]dioxaphosphol-4-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]azanium
• CAS: 140391-24-8
• 化学式: C₁₂H₂₂NO₁₂P
• 分子量: 403.28
• InChiKey: ZULNQPCZALKHMF-LBZOJLJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  222
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 为溶剂， 以20%的产率得到(3aS,4R,5S,6S,7R,7aR)-2,5,6,7-四羟基-2-氧代六氢-1,3,2-苯并二氧磷杂戊环-4-基 2-氨基-2-脱氧-alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  1D-4-O-和1D-6-O-（2-氨基-2-脱氧-α-D-吡喃葡萄糖基）-肌醇1-磷酸酯和1D-6的合成和可能的胰岛素样活性研究-O-（2-氨基-2-脱氧-α-D-吡喃葡萄糖基）-肌醇1，2-（环状磷酸酯）。

  摘要：

  从先前合成的中间体开始，报道了糖基-肌醇1-磷酸酯1和2以及糖基-肌醇1，2-（环状磷酸酯）3的合成。发现化合物3对雏鸡胚胎的早期发育的内耳显示出增殖作用。

  DOI：

  10.1016/0008-6215(94)00178-2

文献信息

• Synthesis of inositol phosphoglycans containing thiol-terminated spacers for efficient coupling to maleimide functionalized solid phases or proteins
  作者：Jan Lindberg、Peter Strålfors、Peter Konradsson

  DOI：10.1016/s0040-4020(02)00359-9

  日期：2002.5

  The synthesis of inositol phosphoglycans (IPGs), analogous to second messengers of insulin, to provide a small targeted library of compounds is described. These derivatives contain the glucosamine(α1–6)myo-inositol 1,2-cyclic phosphate motif. A thiol-terminated spacer was introduced, for their immobilization, by a radical elongation of an allyl ether with benzyl mercaptane.

  描述了类似于胰岛素的第二信使的肌醇磷酸聚糖（IPG）的合成，以提供小的目标化合物库。这些衍生物含有葡糖胺（α1-6）肌醇肌醇-1,2-环磷酸基序。通过烯丙基醚与苄基硫醇的自由基伸长，引入了巯基封端的间隔基，以使其固定。
• Glycosyl Inositol Derivatives Related to Inositolphosphoglycan Mediators: Synthesis, Structure, and Biological Activity
  作者：Hansjörg Dietrich、Juan Felix Espinosa、José Luis Chiara、Jesús Jimenez-Barbero、Yolanda Leon、Isabel Varela-Nieto、José-Maria Mato、Felix H. Cano、Concepción Foces-Foces、Manuel Martín-Lomas

  DOI：10.1002/(sici)1521-3765(19990104)5:1<320::aid-chem320>3.0.co;2-k

  日期：1999.1.4
• Synthesis and characterization of an insulin-mimetic disaccharide
  作者：Robert Plourde、Marc D'Alarcao、Alan R. Saltiel

  DOI：10.1021/jo00035a015

  日期：1992.4

  A glucosaminyl-inositol-1,2-cyclic phosphate, 1, has been synthesized and evaluated for selected insulin-mimetic properties. The compound was designed to resemble structurally the recently reported inositol glycans which are believed to be insulin second messengers. The synthesis utilized a Koenigs-Knorr glycosylation of optically pure 1-camphanyl-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol with 2-azido-3,4,6-tri-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide followed by phosphitylation by the phosphoramidite method, oxidation, and carbodiimide cyclization. Compound 1 was found to stimulate lipogenesis in rat adipocytes in a dose-dependent manner in the micromolar range up to a level 30-40% of that maximally induced by insulin.
• Tetramerization of Glycosylphosphatidylinositol-specific Phospholipase C from Trypanosoma brucei
  作者：Dora Abena Armah、Kojo Mensa-Wilmot

  DOI：10.1074/jbc.m001798200

  日期：2000.6

  Glycosylphosphatidylinositol-specific phospholipase C (GPI-PLC) is an integral membrane protein in the protozoan parasite Trypanosoma brucei, Enzyme activity appears to be suppressed in T, brucei, although the polypeptide is readily detectable. The basis for the apparent quiescence of GPI-PLC is not known. Protein oligomerization was investigated as a possible mechanism for post-translational regulation of GPI-PLC activity, An equilibrium between monomers, dimers, and tetramers of purified GPI-PLC was detected by molecular sieving and shown to be perturbed with specific detergents. Homotetramers dominated in Nonidet P-40, and dimers and monomers of GPI-PLC were the major species in 3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate. The detergents were exploited as tools to study the effect of oligomerization on enzyme activity. Tetrameric GPI-PLC was 3.6-20-fold more active than the monomeric enzyme. Tetramer existence was confirmed by chemical cross-linking. In vivo cross-linking revealed the oligomeric state of GPI-PLC during latency and after enzyme activation. During quiescence, monomers were the predominant species in T, brucei, Assembly of tetrameric GPI-PLC occurred when parasites were subjected to conditions known to activate the enzyme. In Leishmania where heterologous expression of GPI-PLC causes a GPI deficiency, the enzyme existed as a tetramer, Hence, oligomerization of GPI-PLC is associated with high enzyme activity both in vivo and in vitro.
• Hereld D.; Krakow J.L.; Bangs J.D., J Biol Chem, 1986, 0021-9258, 13813-9
  作者：Hereld D.、Krakow J.L.、Bangs J.D.、Hart G.W.、Englund P.T.

  DOI：——

  日期：——