2-氨基-3-[2-(2-氨基-2-羧基-乙基)硫基乙基硫基]丙酸 | 14344-49-1

• 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
• 中文名称: 2-氨基-3-[2-(2-氨基-2-羧基-乙基)硫基乙基硫基]丙酸
• 英文名称: S,S'-ethanediyl-bis-L-cysteine
• 英文别名: S,S'-ethylenebis(L-cysteine)；S,S'-ethanediyl-di-L-cysteine；S,S'-Aethandiyl-di-L-cystein；1,2-Bis-((R)-2-Amino-2-carboxy-aethylmercapto)-aethan；(2R)-2-azaniumyl-3-[2-[(2R)-2-azaniumyl-2-carboxylatoethyl]sulfanylethylsulfanyl]propanoate
• CAS: 14344-49-1
• 化学式: C₈H₁₆N₂O₄S₂
• 分子量: 268.358
• InChiKey: MJARHCRAWLXDKO-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2-氨基-3-[2-(2-氨基-2-羧基-乙基)硫基乙基硫基]丙酸 在 盐酸 、 sodium hydroxide 、 potassium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 162.0h， 生成
  参考文献：
  名称：

  Rational Approaches to the Design of Cationic Gemini Surfactants for Gene Delivery

  摘要：

  We report a new class of amphiphilic gemini surfactants as vehicles for gene delivery into cells, and the beginnings of a systematic structure-activity study. Preliminary results suggest that combining gemini surfactants with dioleoylphosphatidylethanolamine (DOPE) should allow the preparation of liposomes of various sizes and lipid compositions. Control of such colloidal changes could be as significant as the changes in the molecular composition of the gemini surfactants in delivering optimum gene expression in animal models.

  DOI：

  10.1021/ja005681c
• 作为产物：
  描述：

  L-半胱氨酸盐酸盐无水物 、 1,2-二溴乙烷 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-氨基-3-[2-(2-氨基-2-羧基-乙基)硫基乙基硫基]丙酸
  参考文献：
  名称：

  Daebritz,E.; Virtanen,A.I., Chemische Berichte, 1965, vol. 98, p. 781 - 788

  摘要：

  DOI：

文献信息

• CONJUGATES DERIVED FROM NON-STEROIDAL ANTI-INFLAMMATORY DRUGS AND METHODS OF USE THEREOF IN IMAGING
  申请人：Reiley Pharmaceuticals, Inc.

  公开号：US20150374858A1

  公开（公告）日：2015-12-31

  Conjugates derived from non-steroidal anti-inflammatory drugs (NSAIDs) and methods of use thereof are disclosed, useful for, inter alia, identifying and localizing the site of pathology and/or inflammation responsible for the sensation of pain in a patient; for identifying the sites of primary, secondary, benign, or malignant tumors; and for diagnosing infection or confirming or ruling out suspected infection. The NSAID-based conjugates contain an imaging moiety. The conjugates concentrate at sites of increased cyclooxygenase expression, thus revealing the sites of increased prostaglandin production, which is correlated with pain and inflammation, and correlated with tumor presence and/or location. Identifying areas of increased COX expressing can also aid in screening for infections.

  披露了来自非甾体抗炎药（NSAIDs）的衍生物及其使用方法，这对于识别和定位患者疼痛感觉的病理和/或炎症部位；识别原发、继发、良性或恶性肿瘤的部位；以及诊断感染或确认或排除疑似感染非常有用。基于NSAID的偶联物含有成像基团。这些偶联物在环氧化酶表达增加的部位富集，从而揭示了前列腺素产生增加的部位，这与疼痛和炎症有关，并与肿瘤存在和/或位置有关。识别COX表达增加的区域也有助于筛查感染。
• Macrocycles with sulfide and amine binding sites as chiral ligands for nickel catalyzed cross coupling of a grignard reagent with vinyl bromide
  作者：Marc Lemaire、Bindert K. Vriesema、Richard M. Kellogg

  DOI：10.1016/s0040-4039(00)98674-x

  日期：1985.1

  Synthetic routes to macrocycles derived from (S)-phenyl alanine and (S)-cysteine have been developed. The catalyzed coupling of the Grignard reagent of 1-chloro-1-phenylethane and vinyl bromide in the presence of these ligands proceeds usually in good yields and in enantiomeric excesses (e.e.) of up to 46%.

  已经开发了从（S）-苯基丙氨酸和（S）-半胱氨酸衍生到大环的合成途径。在这些配体的存在下，1-氯-1-苯基乙烷的格氏试剂和溴化​​乙烯的催化偶联通常以良好的收率和高达46％的对映体过量（ee）进行。
• Dimerization of an intermediate during the sodium in liquid ammonia reduction of <scp>l</scp>-thiazolidine-4-carboxylic acid
  作者：P. Blondeau、C. Berse、D. Gravel

  DOI：10.1139/v67-009

  日期：1967.1.1

  Reduction with sodium in liquid ammonia of l-thiazolidine-4-carboxylic acid (II) leads, depending on the reaction procedure followed, to N-methyl-l-cysteine (I) or a mixture of N-methyl-l-cysteine (I) (30%) and a dimer (50%), the structure of which is shown to be VI. Contrary to what has been expressed in the literature, the reaction of 1,2-dichloroethane with cysteine (III) at a pH of 8–10 does not

  在液氨中用钠将 l-噻唑烷-4-羧酸 (II) 还原，取决于随后的反应程序，生成 N-甲基-l-半胱氨酸 (I) 或 N-甲基-l-半胱氨酸的混合物 ( I) (30%) 和二聚体 (50%)，其结构显示为 VI。与文献中所表达的相反，1,2-二氯乙烷与半胱氨酸 (III) 在 8-10 的 pH 值下反应不会生成化合物 VI，而是生成化合物 VIII。
• Preparation and Stereochemistry of Cobalt(III) Complexes with<i>S</i>-Alkyl-L-cysteinate,<i>N</i>,<i>N</i>′-Trimethylenebis(<i>S</i>-methyl-L-cysteinate), and<i>S</i>,<i>S</i>′-Ethylene(or -Trimethylene)bis(L-cysteinate)
  作者：Takumi Konno、Ken-ichi Okamoto、Jinsai Hidaka

  DOI：10.1246/bcsj.56.2631

  日期：1983.9

  steinate) (L,L-tbc). Three isomers, trans(S), trans(N), and trans(O), were chromatographically isolated for each of the bis L-sec and L-sbc complexes, while only the trans(O) isomer was isolated for each of the L,L-tbsmc, L,L-ebc, and L,L-tbc complexes. These isomers were characterized from their absorption, CD, and 1H and 13C NMR spectra. The trans(O) isomers of the bis type and L,L-tbsmc complexes

  制备了五种[Co(terdentate-N,S,O)2]和[Co(sexidentate-N2,S2,O2)]型钴(III)配合物；此处三齿-N,S,O 表示 S-乙基-L-半胱氨酸 (L-sec) 和 S-苄基-L-半胱氨酸 (L-sbc)，而六齿-N2,S2,O2 表示 N,N'-三亚甲基双(S-甲基-L-半胱氨酸) (L,L-tbsmc)、S,S'-亚乙基双(L-半胱氨酸) (L,L-ebc) 和 S,S'-三亚甲基双(L-半胱氨酸) (L ,L-tbc)。两种双 L-sec 和 L-sbc 复合物的三种异构体，反式 (S)、反式 (N) 和反式 (O) 被色谱分离，而每个复合物仅分离反式 (O) 异构体L,L-tbsmc、L,L-ebc 和 L,L-tbc 复合物。这些异构体的特征在于它们的吸收、CD 以及 1H 和 13C NMR 光谱。bis 型的反式 (O) 异构体和 L,L-tbsmc
• Nachtomi,E. et al., Israel Journal of Chemistry, 1966, vol. 4, p. 239 - 246
  作者：Nachtomi,E. et al.

  DOI：——

  日期：——