[(tert-butylthio)carbonyl]acetic acid magnesium salt | 110330-14-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(tert-butylthio)carbonyl]acetic acid magnesium salt
• CAS: 110330-14-8
• 化学式: 2C₇H₁₁O₃S*Mg
• 分子量: 374.762
• InChiKey: KWZZKPQWWHKLDY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.2
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  甲基丙二酸氢 、 [(tert-butylthio)carbonyl]acetic acid magnesium salt 在 N,N'-羰基二咪唑 作用下， 生成 methyl 5-tert-butylsulfanyl-3,5-dioxopentanoate
  参考文献：
  名称：

  Remote substituent effects in microbial reductions of 3-ketoglutarate and 3-ketoadipate esters

  摘要：

  DOI：

  10.1016/s0040-4039(01)91216-x

文献信息

• Is RK-682 a promiscuous enzyme inhibitor? Synthesis and in vitro evaluation of protein tyrosine phosphatase inhibition of racemic RK-682 and analogues
  作者：Vânia M.T. Carneiro、Daniela B.B. Trivella、Valéria Scorsato、Viviane L. Beraldo、Mariana P. Dias、Tiago J.P. Sobreira、Ricardo Aparicio、Ronaldo A. Pilli

  DOI：10.1016/j.ejmech.2015.04.036

  日期：2015.6

  compounds, including racemic analogues of 1, dihydropyranones and C-acylated Meldrum's acid derivatives, the later obtained in one synthetic step from commercially available starting material. We further characterized the behavior of some representative compounds in aqueous solution and evaluated their in vitro PTPase binding and inhibition. Our data reveal that rac-1 and some derivatives are able to form

  RK-682（1）是已知可选择性抑制蛋白质酪氨酸磷酸酶（PTPases）的天然产物，并在商业上用作体外测定中抑制磷酸酶的阳性对照。蛋白质磷酸酶与多种人类疾病有关，包括糖尿病，癌症和炎症，被认为是药物开发的重要靶标。在这里，我们报告外消旋RK-682（rac - 1）和一组重点化合物的合成，包括1，二氢吡喃酮和C的外消旋类似物-酰化的麦德鲁姆酸衍生物，后者在一个合成步骤中从可商购的起始原料中获得。我们进一步表征了某些代表性化合物在水溶液中的行为，并评估了它们在体外的PTPase结合和抑制作用。我们的数据表明，rac - 1和某些衍生物能够在溶液中形成大的聚集体，其中聚集能力取决于酰基侧链的大小。然而，化合物聚集本身不能促进PTPase抑制。我们的数据揭示了一个新的PTPase抑制剂家族（C酰化的Meldrum酸衍生物）以及rac - 1并且具有暴露的潜在带负电荷的亚结构的衍生物（例如1的te
• Asymmetric Synthesis of a 3-Acyltetronic Acid Derivative, RK-682, and Formation of Its Calcium Salt during Silica Gel Column Chromatography.
  作者：Mikiko SODEOKA、Ruriko SAMPE、Sachiko KOJIMA、Yoshiyasu BABA、Naoko MORISAKI、Yuichi HASHIMOTO

  DOI：10.1248/cpb.49.206

  日期：——

  RK-682 was reported to be a potent protein tyrosine phosphatase inhibitor. We found that (R)-3-hexadecanoyl-5-hydroxymethyltetronic acid (1) was easily converted to its calcium salt during column chromatography on Silica gel 60, and this calcium salt was identical to RK-682 originally isolated from a natural source. Here we report details of the asymmetric synthesis of (R)-1 and its conversion to the calcium salt. Fast atom bombardment mass spectrometric (FAB-MS) analysis of the free and calcium salt forms of RK-682 is also reported.

  据报道，RK-682 是一种有效的蛋白酪氨酸磷酸酶抑制剂。我们发现(R)-3-十六酰基-5-羟甲基特窗酸(1)在硅胶60柱层析过程中很容易转化为其钙盐，并且这种钙盐与最初从天然来源分离的RK-682相同。在这里，我们报告了 (R)-1 的不对称合成及其转化为钙盐的详细信息。还报道了 RK-682 游离形式和钙盐形式的快原子轰击质谱 (FAB-MS) 分析。
• A convergent synthetic strategy for the polyene macrolide pimaricin
  作者：Dee W. Brooks、James T. Palmer

  DOI：10.1016/s0040-4039(00)88094-6

  日期：1983.1

  The synthesis of two chiral fragments representing Cl-11 and C12-25 of the polyene macrolide pimaricin from dimethyl 3-hydroxyglutarate is described.

  描述了由3-羟基戊二酸二甲酯合成代表多烯大环内酯比马星霉素的Cl-11和C12-25的两个手性片段。
• Asymmetric synthesis of RK-682 and its analogs, and evaluation of their protein phosphatase inhibitory activities
  作者：Mikiko Sodeoka、Ruriko Sampe、Terumi Kagamizono、Hiroyuki Osada

  DOI：10.1016/s0040-4039(96)02029-1

  日期：1996.11

  We report an asymmetric synthesis of a potent tyrosine phosphatase inhibitor, RK-682 and its analogs. The absolute stereochemistry of RK-682 was determined to be (R). The inhibitory activities of RK-682 and its analogs, (R)-1a, (S)-1a, (R)-1b and (R)-1c toward various protein phosphatases (MIR, cdc25A, cdc25B, and PP1) are also reported. Copyright (C) 1996 Elsevier Science Ltd
• Total synthesis of debromoaplysiatoxin and aplysiatoxin
  作者：Pyeong Uk Park、Chris A. Broka、Bruce F. Johnson、Yoshito Kishi

  DOI：10.1021/ja00254a062

  日期：1987.9