N,N'-dimethyl L-cystine | 14000-26-1

• 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
• 英文名称: N,N'-dimethyl L-cystine
• 英文别名: N,N'-Dimethyl-L-cystin；(2R)-3-[[(2R)-2-carboxy-2-(methylamino)ethyl]disulfanyl]-2-(methylamino)propanoic acid
• CAS: 14000-26-1
• 化学式: C₈H₁₆N₂O₄S₂
• 分子量: 268.358
• InChiKey: MDYMLKDYGJSKKU-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 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：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-dimethyl L-cystine 在 盐酸 、 溴 作用下， 生成 N-Methyl-L-cysteinsaeure
  参考文献：
  名称：

  放线菌的代谢产物。第十五次沟通。棘皮霉素的组成†

  摘要：

  对于先前的2）3）分离的抗生素棘球霉素，根据已知的和新的分析数据以及降解结果，得出了新的化学式C 50 H 60 O 12 N 12 S 2。该式对应于不寻常的结构XIII，即具有由二噻吩环桥接的26个环成员的环八肽-二内酯。

  DOI：

  10.1002/hlca.19590420127
• 作为产物：
  描述：

  N-甲基-L-半胱氨酸 在 ferrous(II) sulfate heptahydrate 作用下， 以 水 为溶剂， 反应 24.0h， 生成 N,N'-dimethyl L-cystine
  参考文献：
  名称：

  棘霉素的全合成及其类似物。

  摘要：

  棘霉素的第一个全合成（1）是通过Pummerer重排和同时环化以及肽链的双向延伸以构建C 2对称的双环八环十八肽桥联的硫缩醛部分的后期构建而完成的带有硫键。该策略可以适用于多种棘霉素的类似物。

  DOI：

  10.1021/acs.orglett.0c01268

文献信息

• Cystine Diamide Analogs for the Prevention of Cystine Stone Formation in Cystinuria
  申请人：Rutgers, The State University of New Jersey

  公开号：US20140187546A1

  公开（公告）日：2014-07-03

  Cystine analogs that improve the solubility of L-cystine in urine for treatment of cystinuria and which have the structure: and pharmaceutically acceptable salts, solvates and prodrugs thereof, wherein each R and R′ pair are independently selected from (i) or (ii); (i) R and R′ are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alcohol, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic, and substituted or unsubstituted heteroaryl, or (ii) R and R′ together form a substituted or unsubstituted heterocyclic ring structure, or a substituted or unsubstituted heteroaryl ring structure; X is hydrogen, or an alkyl; and Y is O or S.

  改善L-半胱氨酸在尿液中的溶解度以治疗囊胱氨酸尿症的半胱氨酸类似物，其结构为：以及其药用可接受的盐、溶剂化合物和前药，其中每个R和R′对均独立地从(i)或(ii)中选择；(i) R和R′均独立地从氢、取代或未取代的烷基、取代或未取代的烯基、取代或未取代的醇、取代或未取代的芳基、取代或未取代的环烷基、取代或未取代的杂环基和取代或未取代的杂芳基中选择，或(ii) R和R′共同形成取代或未取代的杂环戒结构或取代或未取代的杂芳环结构；X为氢或烷基；Y为O或S。
• Design, synthesis, and evaluation of l-cystine diamides as l-cystine crystallization inhibitors for cystinuria
  作者：Yanhui Yang、Haifa Albanyan、Sumi Lee、Herve Aloysius、Jian-Jie Liang、Vladyslav Kholodovych、Amrik Sahota、Longqin Hu

  DOI：10.1016/j.bmcl.2018.03.024

  日期：2018.5

  inhibitory activity of l-cystine crystallization. Computational modeling indicates that Nα-methylation leads to significant decrease in binding of the l-cystine diamides to l-cystine crystal surface. Among the l-cystine diamides 2a–i, l-cystine bismorpholide (CDMOR, LH707, 2g) and l-cystine bis(N′-methylpiperazide) (CDNMP, LH708, 2h) are the most potent inhibitors of l-cystine crystallization.

  为了克服的化学和代谢稳定性的问题升-cystine二甲酯（CDME）和升-cystine甲酯（CME），一系列的升带或不带二酰胺-cystine Ñ α -methylation被设计，合成并评价了它们的l-胱氨酸结晶的抑制活性。升-Cystine二酰胺2A -我不Ñ α -methylation被发现是有效的抑制剂升-cystine结晶而Ñ α的-methylation升-cystine二酰胺导致衍生物3b的-我没有1-胱氨酸结晶的任何抑制活性。计算建模表明Ñ α -methylation导致显著降低在结合升-cystine二酰胺向升-cystine晶体表面。间的升-cystine二酰胺2A -我，升-cystine bismorpholide（CDMOR，LH707，2克）和升-cystine双（N' -methylpiperazide）（CDNMP，LH708，2H）是最有效的抑制剂升-cystine结晶。
• Cystine diamide analogs for the prevention of cystine stone formation in cystinuria
  申请人：Rutgers, The State University of New Jersey

  公开号：US09428453B2

  公开（公告）日：2016-08-30

  Cystine analogs that improve the solubility of L-cystine in urine for treatment of cystinuria and which have the structure: and pharmaceutically acceptable salts, solvates and prodrugs thereof, wherein each R and R′ pair are independently selected from (i) or (ii); (i) R and R′ are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alcohol, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic, and substituted or unsubstituted heteroaryl, or (ii) R and R′ together form a substituted or unsubstituted heterocyclic ring structure, or a substituted or unsubstituted heteroaryl ring structure; X is hydrogen, or an alkyl; and Y is O or S.

  改善L-半胱氨酸在尿液中的溶解度以治疗囊性尿路结石的半胱氨酸类似物，其结构如下所示：其药学上可接受的盐，溶剂化合物和前药，其中每个R和R'对都是独立地从（i）或（ii）中选择的；（i）R和R'独立地选择自氢，取代或未取代的烷基，取代或未取代的烯基，取代或未取代的醇基，取代或未取代的芳基，取代或未取代的环烷基，取代或未取代的杂环基，和取代或未取代的杂环芳基；或（ii）R和R'一起形成一个取代或未取代的杂环环结构，或一个取代或未取代的杂环芳基环结构；X是氢或烷基；Y是O或S。
• Disulfide stereochemistry. Conformations and chiroptical properties of L-cystine derivatives
  作者：Jeremiah P. Casey、R. Bruce Martin

  DOI：10.1021/ja00772a036

  日期：1972.8
• Anatomy of a Gel. Amino Acid Derivatives That Rigidify Water at Submillimolar Concentrations
  作者：Fredric M. Menger、Kevin L. Caran

  DOI：10.1021/ja0016811

  日期：2000.11.1

  On the basis of suggestive X-ray data, 14 aroyl L-cystine derivatives were designed, synthesized, and examined for their ability to gelate water. Several members of this amino acid family are remarkably effective aqueous gelators (the best being one that can rigidify aqueous solutions at 0.25 mM, ca. 0.01%, in less than 30 s!). A few of the analogues separate from water as crystals, indicating a close relationship between gelation and crystallization. All effective gelators self-assemble into fibrous structures that entrain the solvent in the capillary spaces among them. Hydrogen-bonding sites on the compounds that might stabilize the fibers were identified from specific substitutions that replace a hydrogen donor with a methyl group, enhance the hydrogen-accepting ability of a carbonyl oxygen, or promote the hydrogen-donating, ability of an amide proton. The structural variations were characterized via minimal gelation concentrations and times, X-ray crystallography, light and electron microscopy, rheology, and calorimetry. The multiple techniques, applied to the diverse compounds, allowed an extensive search into the basis of gelation. It was learned, for example, that the compound with the lowest minimum gelator concentration and time also has one of the weakest gels (i.e., it has a low elastic modulus). This is attributed to kinetic effects that perturb the length of the fibers. It was also argued that pi/pi stacking, the carboxyl carbonyl (but not the carboxyl proton), and solubility factors all contribute to the stability of a fiber. Polymorphism also plays a role. Rheological studies at different temperatures show that certain gels are stable to a 1-Hz, 3-Pa oscillating shear stress at temperatures as high as 90 degreesC. Other gels have a "catastrophic" break at lower temperatures. Calorimetric data indicate a smooth transition from gel to sol as the temperature is increased. These and other issues are discussed in this "anatomy" of a gel.