L-半胱氨酸乙酯 | 3411-58-3

• 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: L-半胱氨酸乙酯
• 英文名称: L-cystein ethyl ester
• 英文别名: l-cysteine ethyl ester；cysteine ethyl ester；ethyl L-cysteinate；L-cysteine ethyl ester hydrochloride；L-Cys-OEt；ethyl (2R)-2-amino-3-sulfanylpropanoate
• CAS: 3411-58-3
• 化学式: C₅H₁₁NO₂S
• mdl: MFCD00137424
• 分子量: 149.214
• InChiKey: YVKSGVDJQXLXDV-BYPYZUCNSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  205.9±30.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  53.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  (S)-亚硝基-L-半胱氨酸乙酯	(S)-nitroso-L-cysteine ethyl ester	166667-89-6	C5H10N2O3S	178.212
  L-半胱氨酸	L-Cysteine	52-90-4	C3H7NO2S	121.16

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  (S)-亚硝基-L-半胱氨酸乙酯	(S)-nitroso-L-cysteine ethyl ester	166667-89-6	C5H10N2O3S	178.212
  L-胱氨酸二乙酯二盐酸盐	L-cystine diethyl ester	583-89-1	C10H20N2O4S2	296.412

反应信息

• 作为反应物：
  描述：

  L-半胱氨酸乙酯 在 硫化氢 、 mercury(II) diacetate 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 4.08h， 生成 (2S)-2-氨基-5-[[(2R)-1-乙氧基-1-氧代-3-巯基丙-2-基]氨基]-5-氧代戊酸
  参考文献：
  名称：

  Augmentation of Human and Rat Lenticular Glutathione in Vitro by Prodrugs of γ-l-Glutamyl-l-cysteine

  摘要：

  A marked age-related decrease in glutathione (GSH) levels as well as depression of gamma-glutamylcysteine synthetase activity are factors that are believed to render the aged lens more susceptible to oxidative stress and, therefore, to cataractogenesis. Providing gamma-L-glutamyl-L-cysteine, the dipeptide precursor of GSH, would effectively bypass the compromised first step in its biosynthesis and should protect the lens from GSH depletion. Accordingly, some bioreversible sulfhydryl-, amino-, and C-terminal carboxyl-protected prodrug forms of this dipeptide were prepared. Sulfhydryl protection was in the form of an acetyl thioester, while the carboxyl group was protected as the ethyl ester. These prodrugs were evaluated for their GSH-enhancing activity in cultured human and rat lenses in vitro using an assay that measured the incorporation of [C-14]glycine into lens GSH. Ethyl S-acetyl-gamma-L-glutamyl-L-cysteinate (2) raised GSH levels in human lenses by 25% and in rat lenses by >150%. These data suggest that 2 may have potential as an anticataract agent since ethyl gamma-L-glutamyl-L-cysteinate (1a), the des-S-acetyl analog of 2, had been shown (by others) to protect against experimental rodent cataracts. GSH augmentation by 1a was 2% in human lenses and 25% in rat lenses, considerably less than that shown by 2.

  DOI：

  10.1021/jm950674y
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 锌 作用下， 生成 L-半胱氨酸乙酯
  参考文献：
  名称：

  半胱氨酸

  摘要：

  Durch Reduktion vonS-Äthylcystein-Äthylester-hydrochloredmit Natrium und Phenol和vonL-Cystein-Äthylestermit Lithiumaluminiumhydrium wurden die entsprechenden Aminoalkohole erhalten。左旋半胱氨酸盐酸盐中的Es wurde O，N，S-三乙酰基-半胱氨酸异氰酸酯和durch Verseifung。

  DOI：

  10.1002/hlca.19610440314

文献信息

• A Concise Synthesis of the HCV Protease Inhibitor BILN 2061 and Its P3 Modified Analogs
  作者：Dejun Liu、Jingchao Dong、Yunxing Yin、Rujian Ma、Yifeng Shi、Hao Wu、Shuhui Chen、Ge Li

  DOI：10.1002/cjoc.201180270

  日期：2011.7

  A concise synthesis of BILN 2061 was achieved through more efficient installation of P2 4‐quinoline moiety via SN2 displacement of the β‐OBs group located on the 4‐hydroxyl proline intermediate, which was prepared from 4‐α‐hydroxyl proline analog via Mitsunobu reaction with inversion of stereochemistry. In addition, a short and practical synthesis for P3 unit is also described herein. Final assembly

  BILN 2061的简明合成是通过更高效地安装P2 4-喹啉部分的方法，该方法是通过用4- α-羟基脯氨酸类似物通过以下方法制备的位于4-羟基脯氨酸中间体上的β- OBs基团的S N 2置换来实现的Mitsunobu反应与立体化学倒置。另外，本文还描述了P3单元的简短而实用的合成。从P1到15a的4步最终完成了BILN 2061的四个片段的最终组装，总产率为58％。的几个另外的类似物BILN 2061（WX-1 -使用对母体抑制剂BILN 2061所述的相同合成路线，成功合成了对P3单元进行了修饰的WX - 5）。
• [EN] METHOD FOR LABELING OF SENSITIVE AND THERMOSENSITIVE TARGETING BIOMOLECULES WITH TECHNETIUM BASED COMPOUNDS<br/>[FR] PROCÉDÉ DE MARQUAGE DE BIOMOLÉCULES DE CIBLAGE SENSIBLES ET THERMOSENSIBLES À L'AIDE DE COMPOSÉS À BASE DE TECHNÉTIUM
  申请人：BRACCO IMAGING SPA

  公开号：WO2018109164A1

  公开（公告）日：2018-06-21

  The present invention relates to a labeling procedure for the incorporation, in mild reaction conditions, of sensitive and thermosensitive targeting molecules into a [99m Tc(N)(PNP)]-based compound suitable for a kit formulation.

  本发明涉及一种标签程序，用于在温和的反应条件下，将敏感和热敏感的靶向分子引入适用于试剂盒配方的基于[99mTc(N)(PNP)]的化合物中。
• Reaction of Thiols with N-Bonded Sulfenamide Complexes of Cobalt(III):  Steric Effect and Reaction Pathway
  作者：Margaret J. Sisley、Michael J. Ferguson、Robert B. Jordan

  DOI：10.1021/ic048926l

  日期：2005.1.1

  The products and kinetics of the reaction of several thiols (RSH = 2-aminoethanethiol, cysteine, penicillamine, cysteine ethyl ester) with N-bonded sulfenamide complexes ([Co(en)(2)(NH(2)S(CH(2))(2)NH(2)](3+) (IA), [Co(en)(2)(NH(2)SCH(2)CH(CO(2)H)NH(2)](3+) (IC), [Co(en)(2)(NH(2)SC(CH(3))(2)CH(CO(2)H)NH(2)](3+) (IP)) have been studied. The reaction proceeds by nucleophilic attack at sulfur with cleavage

  根据这些以及其他文献的观察，由于反应的区域特异性，RC（CH（3））（2）-SXR'单元中的二配位硫在亲核进攻时将有明显的空间阻滞作用。还报道了IP的酸解离常数及其溴化物盐的X射线结构。
• Electrophilic Vinylation of Thiols under Mild and Transition Metal‐Free Conditions
  作者：Laura Castoldi、Ester Maria Di Tommaso、Marcus Reitti、Barbara Gräfen、Berit Olofsson

  DOI：10.1002/anie.202002936

  日期：2020.9

  methodology displays high functional group tolerance and proceeds under mild and transition metal‐free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved

  碘（III）试剂乙烯基苯并恶恶唑酮（VBX）用于乙烯基化一系列脂肪族和芳香族硫醇，从而使E-烯基硫化物具有完全的化学和区域选择性以及出色的立体选择性。该方法具有很高的官能团耐受性，可在温和和无过渡金属的条件下进行，而无需过量的底物或试剂。巯基噻唑可以在改性条件下被乙烯基化，与以前与乙烯基碘鎓盐的反应相比，导致相反的立体选择性。制备了具有取代的苯并恶唑酮核心的新型VBX试剂，发现与二甲基取代的核心相比，反应性得到了改善。
• Nitrosation by alkyl nitrites. Part 6. Thiolate nitrosation
  作者：Hanif M. S. Patel、D. Lyn H. Williams

  DOI：10.1039/p29900000037

  日期：——

  differs significantly from the literature value. With simple alkyl nitrites (ethyl, isopentyl, isopropyl and t-butyl) steric effects appear to be the major influences in reactivity, whereas electron-withdrawing substituents in the 2-position greatly increase the rate constants. The reactions of 2,2,2-trichloroethyl nitrite were too fast to measure at all pH values, whereas the reaction of 2,2-dichloroethyl

  以下每种硫醇在25°C的水中在6-13的pH范围内与一定范围内的亚硝酸烷基酯反应，在溶液中生成相应的亚硝酸盐：L-半胱氨酸，N-乙酰基-L-半胱氨酸，L-半胱氨酸甲酯，L-半胱氨酸乙酯，谷胱甘肽和巯基乙酸。速率常数的pH依赖性清楚地表明，反应仅通过硫醇根阴离子RS –发生。对于Ñ乙酰基大号-半胱氨酸和巯基乙酸只有一个RS -物种是可能的和定量动力学分析产率p ķ一个RSH电离的值与文献值非常吻合。对于每种剩余的硫醇，可能有两个硫醇根离子（NH 2 RS –和NH 3 RS –），所有亚硝酸烷基酯的测得的速率常数通常跟随从公开的显微图中获得的总硫醇根离子浓度（作为pH的函数）。 p K a值。通过计算机将动力学结果拟合到浓度曲线的另一种方法是产生通常与文献值相吻合的微观p K a值。L-半胱氨酸是一个例外，其中测得的（p K a）D值（对于NH 2 -RSH→NH 2 RS –）与文献值明显