N-<<(2,2,2-trichloroethyl)oxy>carbonyl>-L-cysteine tert-butyl ester | 98303-79-8

• 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-<<(2,2,2-trichloroethyl)oxy>carbonyl>-L-cysteine tert-butyl ester
• 英文别名: (R)-tert-butyl 3-mercapto-2-(((2,2,2-trichloroethoxy)carbonyl)amino)propanoate；N-2,2,2-Trichloroethoxycarbonylcysteine tert-butyl ester；Troc-Cys-OBu^t；Troc-cysteine t-butyl ester；tert-butyl (2R)-3-sulfanyl-2-(2,2,2-trichloroethoxycarbonylamino)propanoate
• CAS: 98303-79-8
• 化学式: C₁₀H₁₆Cl₃NO₄S
• 分子量: 352.666
• InChiKey: YJUQALNBTIPRQU-LURJTMIESA-N

物化性质

• 沸点：
  415.0±45.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-<<(2,2,2-trichloroethyl)oxy>carbonyl>-L-cysteine tert-butyl ester 在 氰基磷酸二乙酯 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2R)-3-(3-docosoxypropylsulfanyl)-2-(2,2,2-trichloroethoxycarbonylamino)propanoyl]amino]-3-[(2-methylpropan-2-yl)oxy]propanoyl]amino]-3-[(2-methylpropan-2-yl)oxy]propanoyl]amino]-4-oxobutanoate
  参考文献：
  名称：

  Structure-activity relationship of lipopeptide from outer membrane of Escherichia coli and synthesis of highly immunopotenting lipopeptide derivatives with an achiral lipo-part.

  摘要：

  为了突出脂肽衍生物的结构-活性关系，新近合成了具有非手性脂部分的生物活性高的脂肽衍生物。

  DOI：

  10.1248/cpb.41.627
• 作为产物：
  描述：

  N,N'-bis<<(2,2,2-trichloroethyl)oxy>carbonyl>-L-cystine di-tert-butyl ester 在 1,4-dithio-erythritol 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成 N-<<(2,2,2-trichloroethyl)oxy>carbonyl>-L-cysteine tert-butyl ester
  参考文献：
  名称：

  从大肠杆菌的外膜合成旋光性脂肽类似物。

  摘要：

  光学活性脂肽衍生物的合成已经通过使用手性甘油衍生物来完成。具有（R）-甘油部分的脂肽衍生物显示出比具有（S）-构型的脂肽衍生物更高的促有丝分裂活性。N-2,2,2-三氯乙氧基羰基脂肽衍生物增加了有丝分裂活性。

  DOI：

  10.1248/cpb.39.2590

文献信息

• Synthesis of biologically active pentapeptide analogs of the N-terminal part of lipoprotein from the outer membrane of Escherichia coli.
  作者：Muneaki KURIMURA、Masumi TAKEMOTO、Kazuo ACHIWA

  DOI：10.1248/cpb.38.1110

  日期：——

  Newly synthesized lipopentapeptide derivatives with (R___-)-glycerol moieties showed higher mitogenic activities than those with the (S___-)-configuration.

  新合成的具有(R＿＿-)-甘油分子的脂五肽衍生物比具有(S＿＿-)-构型的脂五肽衍生物具有更高的有丝分裂活性。
• Synthesis of the ABH rings of ecteinascidin 597 using a connective Pummerer-type cyclisation
  作者：Laura H. S. Smith、Trung Thanh Nguyen、Helen F. Sneddon、David J. Procter

  DOI：10.1039/c1cc13992d

  日期：——

  A connective Pummerer-type cyclisation involving a cysteine derivative and an N-benzyl glyoxamide 3 has been applied in an asymmetric synthesis of the protected ABH rings 2 of the antitumour and antimicrobial natural product ecteinascidin 597.

  涉及半胱氨酸衍生物和N-苄基乙二酰胺3的连接性Pummerer型环化已用于抗肿瘤和抗菌天然产物ecteinascidin 597的受保护ABH环2的不对称合成中。
• Conversion of thiosulfinate derivatives of cystine to unsymmetrical cystines and lanthionines by reaction with tris(dialkylamino)phosphines
  作者：Richard K. Olsen、Ganesh D. Kini、William J. Hennen

  DOI：10.1021/jo00222a026

  日期：1985.11
• Synthesis of new P3CS derivatives and their mitogenic activity on in vitro mice splenocytes
  作者：Maria Pappalardo、Ennio Bousquet、Agata Annino、Gabriella Lombardo、Renato Bernardini、Giuseppe Ronsisvalle

  DOI：10.1016/s0014-827x(02)00012-5

  日期：2003.4

  Vaccination against tumors represents a relevant issue in current human cancer therapy. The N-terminal part of the lipoprotein from the outer membrane of Escherichia coli, tripalmitoyl-S-glyceryl-Cys-Ser (P(3)CS) and analogs with longer aminoacidic sequence are polyclonal activators for B-lymphocytes. Previous study reported that their N-2,2,2-trichloroethoxycarbonyl (Troc) derivatives increase immunocyte mitogenic activity. Therefore, in order to obtain compounds of greater activity and to investigate relationships between molecular structure of S-glyceryl skeleton and biological activity, we synthesized new Troc derivatives of P(3)CS. The mitogenicity of compounds was determined in vitro, by measuring in vitro [3H]-thymidine incorporation into splenocytes from Balb/c mice. Concentrations of compounds ranged from 0 to 64 micro g/ml. In particular, S-[2,3-bis(trichloroethoxycarbonyloxy)]-N-trichloroethoxycarbonyl dipeptide derivative exhibited significant mitogenic activity endowed with high pharmacological potency. These new series of compounds could be used as potent immunoadjuvants for the development of novel synthetic vaccines for tumor immunotherapy.
• KURIMURA, MUNEAKI;TAKEMOTO, MASUMI;ACHIWA, KAZUO, CHEM. PHARM. BULL., 38,(1990) N, C. 1110-1112
  作者：KURIMURA, MUNEAKI、TAKEMOTO, MASUMI、ACHIWA, KAZUO

  DOI：——

  日期：——