meso-2,4-dimercaptoglutaric acid | 31413-38-4

• 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: meso-2,4-dimercaptoglutaric acid
• 英文别名: meso-2,4-Dimercapto-glutarsaeure；(2R,4S)-2,4-bis(sulfanyl)pentanedioic acid
• CAS: 31413-38-4
• 化学式: C₅H₈O₄S₂
• 分子量: 196.248
• InChiKey: DFOTUIOEKZIQQZ-WSOKHJQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.6
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2-dithiolane-3,5-dicarboxylic acid 在 碳酸氢钠 、 锌 、 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以28%的产率得到meso-2,4-dimercaptoglutaric acid
  参考文献：
  名称：

  Structural characterization of 1,3-propanedithiols that feature carboxylic acids: Homologues of mercury chelating agents

  摘要：

  The molecular structures of a series of 1,3-propanedithiols that contain carboxylic acid groups, namely rac- and meso-2,4-dimercaptoglutaric acid (H(4)DMGA) and 2-carboxy-1,3-propanedithiol (H3DMCP), have been determined by X-ray diffraction. Each compound exhibits two centrosymmetric intermolecular hydrogen bonding interactions between pairs of carboxylic acid groups, which result in a dimeric structure for H3DMCP and a polymeric tape-like structure for rac- and meso-H(4)DMGA. Significantly, the hydrogen bonding motifs observed for rac- and meso-H(4)DMGA are very different to those observed for the 1,2-dithiol, rac-2,3-dimercaptosuccinic acid (rac-H(4)DMSA), in which the two oxygen atoms of each carboxylic acid group hydrogen bond to two different carboxylic acid groups, thereby resulting in a hydrogen bonded sheet-like structure rather than a tape. Density functional theory calculations indicate that 1,3-dithiolate coordination to mercury results in larger S-Hg-S bond angles than does 1,2-dithiolate coordination, but these angles are far from linear. As such, kappa(2)-S-2 coordination of these dithiolate ligands is expected to be associated with mercury coordination numbers of greater than two. In vivo studies demonstrate that both rac-H(4)DMGA and H3DMCP reduce the renal burden of mercury in rats, although the compounds are not as effective as either 2,3-dimercaptopropane-1-sulfonic acid (H3DMPS) or meso-H(4)DMSA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.05.012

文献信息

• Schotte, Arkiv foer Kemi, 1956, vol. 9, p. 441,458
  作者：Schotte

  DOI：——

  日期：——
• The 2,4-dimercaptoglutaric acids and corresponding dithiolanes and dithianes
  作者：Mats-Olov Hedblom

  DOI：10.1016/s0040-4039(00)96965-x

  日期：1970.1
• Hedblom, Swedish Journal of Agricultural Research, 1971, vol. 1, p. 43,47
  作者：Hedblom

  DOI：——

  日期：——
• Structural characterization of 1,3-propanedithiols that feature carboxylic acids: Homologues of mercury chelating agents
  作者：Wesley Sattler、Joshua H. Palmer、Christy C. Bridges、Lucy Joshee、Rudolfs K. Zalups、Gerard Parkin

  DOI：10.1016/j.poly.2013.05.012

  日期：2013.11

  The molecular structures of a series of 1,3-propanedithiols that contain carboxylic acid groups, namely rac- and meso-2,4-dimercaptoglutaric acid (H(4)DMGA) and 2-carboxy-1,3-propanedithiol (H3DMCP), have been determined by X-ray diffraction. Each compound exhibits two centrosymmetric intermolecular hydrogen bonding interactions between pairs of carboxylic acid groups, which result in a dimeric structure for H3DMCP and a polymeric tape-like structure for rac- and meso-H(4)DMGA. Significantly, the hydrogen bonding motifs observed for rac- and meso-H(4)DMGA are very different to those observed for the 1,2-dithiol, rac-2,3-dimercaptosuccinic acid (rac-H(4)DMSA), in which the two oxygen atoms of each carboxylic acid group hydrogen bond to two different carboxylic acid groups, thereby resulting in a hydrogen bonded sheet-like structure rather than a tape. Density functional theory calculations indicate that 1,3-dithiolate coordination to mercury results in larger S-Hg-S bond angles than does 1,2-dithiolate coordination, but these angles are far from linear. As such, kappa(2)-S-2 coordination of these dithiolate ligands is expected to be associated with mercury coordination numbers of greater than two. In vivo studies demonstrate that both rac-H(4)DMGA and H3DMCP reduce the renal burden of mercury in rats, although the compounds are not as effective as either 2,3-dimercaptopropane-1-sulfonic acid (H3DMPS) or meso-H(4)DMSA. (C) 2013 Elsevier Ltd. All rights reserved.