(2S,4R)-thiazolidine-2,4-dicarboxylic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4R)-thiazolidine-2,4-dicarboxylic acid
• 英文别名: (2S,4R)-2,4-thiazolidinedicarboxylic acid；(2S,4R)-1,3-thiazolidine-2,4-dicarboxylic acid
• 化学式: C₅H₇NO₄S
• 分子量: 177.181
• InChiKey: DAXBISKSIDBYEU-HRFVKAFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二氯乙酸 、 L-半胱氨酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.5h， 以12.6%的产率得到(2S,4R)-thiazolidine-2,4-dicarboxylic acid
  参考文献：
  名称：

  2,4-噻唑烷二甲酸四种立体异构体的简便制备

  摘要：

  (2R,4R)-2,4-噻唑烷二甲酸 [(2R,4R)-TDA] 通过 L-半胱氨酸 (L-Cys) 与等摩尔量的乙醛酸一水合物 (GLA· H2O) 在醋酸中回流。使用略微过量的 GLA·H2O 的反应在 80 °C 下得到 (2S,4R)-TDA，作为单一的非对映异构体。(2S,4R)-TDA 也是通过 L-Cys 与二氯乙酸在碱性条件下反应合成的。这些以 D-Cys 开始的反应产生 (2S,4S)- 和 (2R,4S)-TDA。

  DOI：

  10.1246/bcsj.71.1911

文献信息

• New Dipeptides Containing Thiazolidine-4-carboxylic Acid Derivatives: Synthesis and Characterization Using NMR Techniques and X-Ray Data.
  作者：Nadia PELLEGRINI、Bernard REFOUVELET、Gregorio CRINI、Olivier BLACQUE、Marek M. KUBICKI、Jean-Francois ROBERT

  DOI：10.1248/cpb.47.950

  日期：——

  New dipeptides, structural analogues of known immunomodulating agents, were prepared by stereospecific condensation between 2-substituted thiazolidine-4-carboxylate esters with N-substituted L-proline or L-thiaproline. The structure of these compounds has been elucidated by combination of NMR methods and X-ray analysis. In addition, NMR measurements on dipeptides indicated the presence of S-cis and S-trans conformers around the amide bonds.

  新二肽是已知免疫调节剂的结构类似物，通过立体特异性缩合2-取代的噻唑烷-4-羧酸酯与N-取代的L-脯氨酸或L-硫代脯氨酸制备。这些化合物的结构已通过NMR方法和X射线分析相结合得以阐明。此外，对二肽的NMR测量表明了在酰胺键周围存在S-顺式和S-反式构象体。
• Thiazolidine-2,4-dicarboxylic acid and its esters: Synthesis, in solution behaviour and regioselective cyclocondensation
  作者：Bernard Refouvelet、Jean-FranÇOis Robert、Jacques Couquelet、Pierre Tronche

  DOI：10.1002/jhet.5570310114

  日期：1994.1

  Thiazolidine-2,4-dicarboxylic acid 2 was obtained as a diastereoisomeric mixture from the condensation of glyoxylic acid with L(-)R-cysteine 1. In solution behaviour studies suggested that the reaction proceeded through an acid catalyzed epimerization mechanism. The methyl esterification of 2 was stereoselective, which can be explained by an interconversion of 2a via a ring seco intermediate. Condensation

  由乙醛酸与L（-）R-半胱氨酸1的缩合得到作为非对映异构体混合物的噻唑烷-2,4-二羧酸2。在溶液中的行为研究表明该反应通过酸催化的差向异构机理进行。的甲基酯化2是立体选择性，其可通过的互变来解释图2a通过一个环开环中间体。二甲基酯3或不对称二酯4与异氰酸苯酯的缩合产生相同的乙内酰脲5。二酯3或4的N-酰化 随后与苄胺的反应是区域选择性的，导致双环衍生物8-10。
• Synthesis, characterization and CO2 uptake of a chiral Co(ii) metal–organic framework containing a thiazolidine-based spacer
  作者：Andrea Rossin、Barbara Di Credico、Giuliano Giambastiani、Maurizio Peruzzini、Gennaro Pescitelli、Gianna Reginato、Elisa Borfecchia、Diego Gianolio、Carlo Lamberti、Silvia Bordiga

  DOI：10.1039/c2jm16236a

  日期：——

  The polytopic ligand thiazolidine-2,4-dicarboxylic acid (H2L) has been synthesised on a large scale starting from the naturally occurring amino acid L-cysteine. The (R,R)/(S,R)diastereomeric mixture has been separated into its constituents through selective precipitation of the pure (R,R) isomer from concentrated H2O/MeOH solutions. The enantiomerically pure ligand (H2L-RR) has been reacted with CoCl2·6H2O under hydrothermal conditions, with the final product being [Co(L-RR)(H2O)·H2O]∞ (1). The obtained coordination polymer is optically pure, and it maintains the chiral information that is present in its building block. Two different kinds of channels are present in the 3D structure of 1: one hydrophobic (with the sulfur atoms of the thiazolidine rings exposed) and the other hydrophilic [with the aquo ligand on Co(II) exposed, and hosting the crystallization water solvent]. 1 has been characterized through a combination of X-ray diffraction (single-crystal and powder) and spectroscopic (CD, IR, UV-Vis, XANES, EXAFS) techniques. Finally, CO2 adsorption tests conducted at 273 K and (pCO2)max = 920 torr have shown a good carbon dioxide uptake, equal to 4.7 wt%.

  以天然存在的氨基酸L-半胱氨酸为起始原料，已大规模合成了多环配体噻唑烷-2,4-二羧酸（H2L）。通过从浓缩的H2O/MeOH溶液中选择性沉淀纯的（R,R）异构体，将（R,R）/（S,R）立体异构体混合物分离为其组分。在高温高压条件下，将光学纯的配体（H2L-RR）与CoCl2·6H2O反应，最终产物为[Co(L-RR)(H2O)·H2O]¨（1）。所获得的配合物聚合物具有光学纯度，并且保留了其构建单元中的手性信息。在1的三维结构中存在两种不同类型的通道：一种疏水性通道（暴露了噻唑烷环的硫原子）和另一种亲水性通道[暴露了Co(II)上的水配体，并容纳了结晶水溶剂]。通过X射线衍射（单晶和粉末）和光谱（CD、IR、UV-Vis、XANES、EXAFS）技术的组合对1进行了表征。最后，在273 K和（pCO2）max = 920 torr条件下进行的CO2吸附测试显示出良好的二氧化碳吸附量，达到4.7 wt%。
• Facile Preparation of Four Stereoisomers of 2,4-Thiazolidinedicarboxylic Acid
  作者：Tadashi Shiraiwa、Takashi Katayama、Takehiro Kaito、Hisashi Tanigawa、Hidemoto Kurokawa

  DOI：10.1246/bcsj.71.1911

  日期：1998.8

  (2R,4R)-2,4-Thiazolidinedicarboxylic acid [(2R,4R)-TDA] was diastereoselectively synthesized in 100% de by condensation of L-cysteine (L-Cys) with an equimolar amount of glyoxylic acid monohydrate (GLA·H2O) in acetic acid under reflux. The reaction employing a slight excess of GLA·H2O afforded (2S,4R)-TDA, as a single diastereomer, at 80 °C. (2S,4R)-TDA was also synthesized by reaction of L-Cys with

  (2R,4R)-2,4-噻唑烷二甲酸 [(2R,4R)-TDA] 通过 L-半胱氨酸 (L-Cys) 与等摩尔量的乙醛酸一水合物 (GLA· H2O) 在醋酸中回流。使用略微过量的 GLA·H2O 的反应在 80 °C 下得到 (2S,4R)-TDA，作为单一的非对映异构体。(2S,4R)-TDA 也是通过 L-Cys 与二氯乙酸在碱性条件下反应合成的。这些以 D-Cys 开始的反应产生 (2S,4S)- 和 (2R,4S)-TDA。