(2R,1'R)-2-amino-3-<(1,2-dicarboxyethyl)sulfanyl>propanoic 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: (2R,1'R)-2-amino-3-<(1,2-dicarboxyethyl)sulfanyl>propanoic acid
• 英文别名: (2R),(1'R)-2-amino-3-(1,2-dicarboxyethylthio)propanoic acid；succinic acid-cysteine；(2R)-2-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanedioic acid
• 化学式: C₇H₁₁NO₆S
• 分子量: 237.233
• InChiKey: XPKKFTKCRVIDAG-IUYQGCFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  L-半胱氨酸 、 (S)-(-)-溴丁二酸 在 sodium hydroxide 作用下， 反应 48.0h， 以60.8%的产率得到(2R,1'R)-2-amino-3-<(1,2-dicarboxyethyl)sulfanyl>propanoic acid
  参考文献：
  名称：

  Optical Resolution of (RS)-Mercaptosuccinic Acid and Syntheses of Four Stereoisomers of 2-Amino-3-1(1,2-dicarboxyethyl)sulfanyl)propanoic Acid.

  摘要：

  为了合成 2-氨基-3-[(1, 2-二羧乙基)硫]丙酸（ADC）的四种立体异构体，以 (1S, 2S)-2- 氨基-1-苯基-1, 3-丙二醇和 (R)- 和 (S)-1- 苯乙胺为分辨剂，对 (RS)-巯基丁二酸[(RS)-MSA]进行了光学分辨，得到了光学纯度为 100%的 (R)- 和 (S)-MSA 。此外，根据熔点、溶解度、红外光谱以及二元和三元相图，研究了(RS)-MSA 的 1-丙基铵盐和 1-丁基铵盐的外消旋结构，目的是通过(RS)-MSA 的优先结晶实现光学分辨。结果表明，(RS)-MSA 的 1-丁基铵盐[(RS)-BA 盐]以团聚体形式存在，而 1-丙基铵盐则形成外消旋化合物。通过对(RS)-BA 盐的优先结晶进行光学解析，得到了光学纯度超过 90% 的(R)-和(S)-BA 盐。通过光学解析得到的(R)-和(S)-MSA 与(R)-和(S)-2-氨基-3-氯丙酸盐酸盐缩合，得到(2R, 1'R)-、(2S, 1'S)-、(2R, 1'S)-和(2S, 1'R)-ADC。此外，这些立体异构体也是由 D-和 L-半胱氨酸以及光学活性溴代丁二酸合成的。

  DOI：

  10.1248/cpb.46.1364

文献信息

• COMPOUND AND PHARMACEUTICAL COMPOSITION FOR TARGETED DRUG DELIVERY
  申请人：SeeCure Taiwan Co., Ltd.

  公开号：US20180326101A1

  公开（公告）日：2018-11-15

  A compound represented by formula (I) is provided, wherein in formula (I), R 1 and R 2 each independently represents hydrogen, O—R 3 or S—R 4 , at least one of R 1 and R 2 is O—R 3 or S—R 4 , and R 3 and R 4 are independently a C 1 to C 10 alkyl group, such that the C 1 to C 10 alkyl group is non-substituted or substituted with at least one selected from the group consisting of —OH, —NH 2 , halogen, ester, ether, and carboxylic acid, and M being a metal or a metal-containing compound. The compound represented by formula (I) is shown to have higher specificity to tumor cells, and is therefore suitable for carrying anti-cancer drugs and/or nuclear imaging agents.

  提供一种由公式（I）表示的化合物，其中在公式（I）中，R1和R2分别表示氢，O—R3或S—R4，R1和R2中至少有一个是O—R3或S—R4，而R3和R4分别是C1到C10的烷基基团，使得C1到C10的烷基基团是非取代的或被至少一种选自—OH，—NH2，卤素，酯，醚和羧酸的基团取代的，M表示金属或含金属化合物。据显示，由公式（I）表示的化合物对肿瘤细胞具有更高的特异性，因此适用于携带抗癌药物和/或核成像剂。
• Compound and pharmaceutical composition for tumor imaging and tumor therapy
  申请人：SeeCure Taiwan Co., Ltd.

  公开号：US10016520B1

  公开（公告）日：2018-07-10

  A compound represented by formula (I) is provided, wherein in formula (I), R1 and R2 each independently represents hydrogen, O—R3 or S—R4, at least one of R1 and R2 is O—R3 or S—R4, and R3 and R4 are independently a C1 to C10 alkyl group, such that the C1 to C10 alkyl group is non-substituted or substituted with at least one selected from the group consisting of —OH, —NH2, halogen, ester, ether, and carboxylic acid, and M being a metal or a metal-containing compound. The compound represented by formula (I) is shown to have higher specificity to tumor cells, and is therefore suitable for carrying anti-cancer drugs and/or nuclear imaging agents.

  提供了一种由式(I)表示的化合物，其中在式(I)中，R1和R2各自独立地表示氢、O—R3或S—R4，R1和R2中至少有一个是O—R3或S—R4，而R3和R4独立地表示C1到C10烷基，使得C1到C10烷基是非取代的或取代的，所取代的基团来自于-OH、-NH2、卤素、酯、醚和羧酸中的至少一种。M是金属或含金属化合物。该式(I)表示的化合物具有更高的肿瘤细胞特异性，因此适合携带抗癌药物和/或核成像剂。
• (2R), (1'R) and (2R), (1'S)-2-Amino-3-(1,2-dicarboxyethylthio)propanoic Acids from Amanita pantherina. Antagonists of N-Methyl-D-aspartic Acid (NMDA) Receptors.
  作者：Shinji FUSHIYA、Qian-Qun GU、Keiko ISHIKAWA、Shinji FUNAYAMA、Shigeo NOZOE

  DOI：10.1248/cpb.41.484

  日期：——

  An antagonist of NMDA-sensitive glutamate receptors in rat brain membrane and rat spinal motoneurones was isolated from Amanita pantherina and ideneified as a diastereoisomeric mixture of 2-amino-3-(1, 2-dicarboxyethylthi)propanoic acids. The mixture was separated and the absolute configurations of the components were determined as (2R), (1'R) and (2R), (1'S), by analysis of the properties.

  从 Amanita pantherina 中分离出一种大鼠脑膜和大鼠脊髓运动神经元中 NMDA 敏感谷氨酸受体的拮抗剂，并鉴定为 2-氨基-3-(1, 2-二羧乙基硫)丙酸的非对映异构体混合物。对混合物进行分离，并通过性质分析确定各组分的绝对构型为 (2R)、(1'R) 和 (2R)、(1'S)。
• COMPOUND AND PHARMACEUTICAL COMPOSITION FOR TUMOR IMAGING AND TUMOR THERAPY
  申请人：SeeCure Taiwan Co., Ltd.

  公开号：US20180193494A1

  公开（公告）日：2018-07-12

  A compound represented by formula (I) is provided, wherein in formula (I), R 1 and R 2 each independently represents hydrogen, O—R 3 or S—R 4 , at least one of R 1 and R 2 is O—R 3 or S—R 4 , and R 3 and R 4 are independently a C 1 to C 10 alkyl group, such that the C 1 to C 10 alkyl group is non-substituted or substituted with at least one selected from the group consisting of —OH, —NH 2 , halogen, ester, ether, and carboxylic acid, and M being a metal or a metal-containing compound. The compound represented by formula (I) is shown to have higher specificity to tumor cells, and is therefore suitable for carrying anti-cancer drugs and/or nuclear imaging agents.
• Optical Resolution of (RS)-Mercaptosuccinic Acid and Syntheses of Four Stereoisomers of 2-Amino-3-1(1,2-dicarboxyethyl)sulfanyl)propanoic Acid.
  作者：Tadashi SHIRAIWA、Masanori OHKUBO、Motoki KUBO、Hideya MIYAZAKI、Masaki TAKEHATA、Hisashi IZAWA、Kazuo NAKAGAWA、Hidemoto KUROKAWA

  DOI：10.1248/cpb.46.1364

  日期：——

  To synthesize four stereoisomers of 2-amino-3-[(1, 2-dicarboxyethyl)sulfanyl]propanoic acid (ADC), (RS)-mercaptosuccinic acid [(RS)-MSA] was optically resolved using (1S, 2S)-2-amino-1-phenyl-1, 3-propanediol and (R)- and (S)-1-phenylethylamine as resolving agents to yield (R)- and (S)-MSA with optical purities of 100%. In addition, the racemic structures of 1-propylammonium and 1-butylammonium salts of (RS)-MSA were examined based on melting point, solubility, infrared spectra, and binary and ternary phase diagrams, with the aim of optical resolution by preferential crystallization of (RS)-MSA. Results indicated that the 1-butylammonium salt of (RS)-MSA [(RS)-BA salt] exists as a conglomerate and that the 1-propylammonium salt forms a racemic compound. Optical resolution by preferential crystallization of (RS)-BA salt yielded (R)- and (S)-BA salts with optical purities of over 90%. The (R)- and (S)-MSA obtained by optical resolution were condensed with (R)- and (S)- 2-amino-3-chloropropanoic acid hydrochlorides to give (2R, 1'R)-, (2S, 1'S)-, (2R, 1'S)-, and (2S, 1'R)-ADC. In addition, these stereoisomers were also synthesized from D- and L-cysteine and optically active bromosuccinic acid.

  为了合成 2-氨基-3-[(1, 2-二羧乙基)硫]丙酸（ADC）的四种立体异构体，以 (1S, 2S)-2- 氨基-1-苯基-1, 3-丙二醇和 (R)- 和 (S)-1- 苯乙胺为分辨剂，对 (RS)-巯基丁二酸[(RS)-MSA]进行了光学分辨，得到了光学纯度为 100%的 (R)- 和 (S)-MSA 。此外，根据熔点、溶解度、红外光谱以及二元和三元相图，研究了(RS)-MSA 的 1-丙基铵盐和 1-丁基铵盐的外消旋结构，目的是通过(RS)-MSA 的优先结晶实现光学分辨。结果表明，(RS)-MSA 的 1-丁基铵盐[(RS)-BA 盐]以团聚体形式存在，而 1-丙基铵盐则形成外消旋化合物。通过对(RS)-BA 盐的优先结晶进行光学解析，得到了光学纯度超过 90% 的(R)-和(S)-BA 盐。通过光学解析得到的(R)-和(S)-MSA 与(R)-和(S)-2-氨基-3-氯丙酸盐酸盐缩合，得到(2R, 1'R)-、(2S, 1'S)-、(2R, 1'S)-和(2S, 1'R)-ADC。此外，这些立体异构体也是由 D-和 L-半胱氨酸以及光学活性溴代丁二酸合成的。