N-palmitoyl-(L)-cysteine | 67603-49-0

• 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-palmitoyl-(L)-cysteine
• 英文别名: L-Cysteine, N-(1-oxohexadecyl)-；(2R)-2-(hexadecanoylamino)-3-sulfanylpropanoic acid
• CAS: 67603-49-0
• 化学式: C₁₉H₃₇NO₃S
• 分子量: 359.574
• InChiKey: YYHOQQKJSHXDEN-KRWDZBQOSA-N

物化性质

• 熔点：
  70.0-72.0 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  527.9±45.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-palmitoyl-(L)-cysteine 生成 硬脂基溴
  参考文献：
  名称：

  Peptide derivatives

  摘要：

  本发明涉及新的脂肽类化合物，特别是公式（1）或（2）中的化合物：其中，R1和R2分别表示具有11-21个碳原子的饱和或不饱和脂肪族或混合脂环族烃基，也可以通过氧功能团被取代；R3表示氢或基团R1-CO-O-CH2-，其中R1具有相同的含义；R1'是至少有9个碳原子的饱和或不饱和脂肪族烃基，可以在不与硫原子相邻的C原子上取代一个自由羟基或羟基酯化的一元羧酸，也可以在C原子链中通过一个或多个氧原子中断，该碳氢化合物可以被最多2个具有5-8个环C原子的脂环族烃基取代；或者R1'是基团-CO-R1"，其中R1"表示具有11-21个C原子的饱和或不饱和脂肪族或混合脂环族烃基，也可以在C原子链中通过氧原子中断；X表示具有自由酯化或酰胺化羧基的氨基酸，或者是由2-10个脂肪族氨基酸组成的氨基酸序列，其末端羧基以自由形式或酯或酰胺形式存在，对于公式（1）的化合物，这些氨基酸是天然的。

  公开号：

  US04439425A1
• 作为产物：
  描述：

  棕榈酸 N-羟基琥珀酰亚胺酯 、 L-半胱氨酸盐酸盐无水物 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以73%的产率得到N-palmitoyl-(L)-cysteine
  参考文献：
  名称：

  Usanova; Sebyakin, Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 5, p. 288 - 291

  摘要：

  DOI：

文献信息

• [EN] IMMUNOSTIMULATING AGENT<br/>[FR] AGENT IMMUNOSTIMULANT
  申请人：AJINOMOTO KK

  公开号：WO2017073797A1

  公开（公告）日：2017-05-04

  The present invention aims to provide an immunostimulating agent superior in an immunostimulatory effect, particularly a compound useful as a vaccine adjuvant, a pharmaceutical composition containing the compound, a vaccine containing the compound and an antigen. The present invention relates to an immunostimulating agent containing at least one kind of a compound represented by the formula (I) : wherein each symbol is as defined in the DESCRIPTION, or a salt thereof, or at least one kind of a compound represented by the formula (II) : wherein each symbol is as defined in the DESCRIPTION, or a salt thereof.

  本发明旨在提供一种免疫刺激剂，其在免疫刺激效果方面优越，特别是作为疫苗佐剂有用的化合物，含有该化合物的药物组合物，含有该化合物和抗原的疫苗。本发明涉及一种免疫刺激剂，其至少包含下式(I)所表示的一种化合物：其中每个符号如描述中所定义，或其盐，或至少包含下式(II)所表示的一种化合物：其中每个符号如描述中所定义，或其盐。
• Peptide Tyrosinase Activators
  申请人：Escape Therapeutics, Inc.

  公开号：US20150152139A1

  公开（公告）日：2015-06-04

  Peptides that increase melanin synthesis are provided. These peptides include pentapeptides YSSWY, YRSRK, and their variants. The peptides may activate the enzymatic activity of tyrosinase to increase melanin synthesis. The pharmaceutical, cosmetic, and other compositions including the peptides are also provided. The methods of increasing melanin production in epidermis of a subject are provided where the methods include administering compositions comprising an amount of one or more peptides effective to increase the melanin production. The methods also include treating vitiligo or other hypopigmentation disorders with compositions including one or more peptides.

  提供了增加黑色素合成的肽类。这些肽包括五肽YSSWY、YRSRK及其变体。这些肽可能激活酪氨酸酶的酶活性，以增加黑色素的合成。还提供了包括这些肽的制药、化妆品和其他组合物。提供了一种增加受试者表皮黑色素产生的方法，其中方法包括给予含有一种或多种肽的组合物的有效量以增加黑色素的产生。这些方法还包括使用包括一种或多种肽的组合物治疗白癜风或其他低色素症。
• Catalytic Efficiency of Synthetic Micellar Catalysts Bearing a Mercapto Group as the Reaction Center
  作者：Yukito Murakami、Akio Nakano、Kiyoshi Matsumoto

  DOI：10.1246/bcsj.52.2996

  日期：1979.10

  In order to obtain a clue to understanding the micro-environmental effect on the reactivity of a mercapto group placed in a reaction center of enzymes, micellar surfactants bearing a mercapto group were synthesized and their catalytic activity in the degradation of p-nitrophenyl carboxylates was studied. N-Hexadecyl-Nα-glutaryl-l-cysteinamide (AM·Cys-1) has an ability to form anionic micelles in aqueous media. The catalytic activity of AM·-Cys-1 was compared with that of another synthetic surfactant, N-hexadecanoyl-l-cysteine (AM·Cys-2). These surfactants below their critical micelle concentrations markedly accelerated the degradation of several p-nitrophenyl carboxylates. On the contrary, the concentration - rate profiles for the degradation of p-nitrophenyl dodecanoate (PNPL) as catalyzed by the surfactants indicate that the reactivity of the mercapto group is reduced upon formation of the anionic micelles. The large rate retardation is primarily due to the decrease in concentration of the active thiolate anion. This was supported by the fact that the pKa values for mercapto groups of the anionic micelles, for which the carboxyl group acts as an anionic head, were increased by 0.8–1.6 pKa unit over those of the corresponding monomeric surfactants in the bulk phase. These surfactants showed profound reactivity even in a neutral pH region when mixed with cationic CTAB micelle. The electrostatic field effect provided by the cationic head of CTAB micelle seems to enhance the nucleophilicity of the mercapto group in the mixed micelles.

  为了获得线索以理解微环境对放置在酶反应中心的巯基反应性的影响，合成了带有巯基的胶束表面活性剂，并研究了它们在降解对硝基苯基羧酸酯中的催化活性。N-十六烷基-Nα-谷酰基-L-半胱氨酸酰胺（AM·Cys-1）具有在水相介质中形成阴离子胶束的能力。将AM·Cys-1的催化活性与另一种合成表面活性剂N-十六酰基-L-半胱氨酸（AM·Cys-2）进行了比较。这些表面活性剂在其临界胶束浓度以下显著加速了几种对硝基苯基羧酸酯的降解。相反，由表面活性剂催化的对硝基苯基十二酸酯（PNPL）降解的浓度-速率关系显示，巯基反应性在形成阴离子胶束后减弱。速率显著减缓主要是由于活性硫酰阴离子浓度的降低。这一点得到了支持，因阴离子胶束的巯基的pKa值（羧基作为阴离子头）比相应的单体表面活性剂在体相中的pKa值增加了0.8-1.6个pKa单位。这些表面活性剂在与阳离子CTAB胶束混合时，即使在中性pH区间也表现出了显著的反应性。CTAB胶束的阳离子头所提供的静电场效应似乎增强了混合胶束中巯基的亲核性。
• Imaging of protease activity in live cells using activity based probes
  申请人：Bogyo S. Matthew

  公开号：US20070036725A1

  公开（公告）日：2007-02-15

  Methods and materials for the imaging of cells containing active proteases such as cathepsin are disclosed. The present materials include activity based probes that bind to an enzyme and are subsequently cleaved. Cleavage results in a fluorescent signal due to removal of a quenching group which, when present on the probe causes altered or no fluorescence. The probes employ an acyloxymethyl ketone reactive group, one or more amino acids for determining specificity, a fluorophore and a quencher. The probes are cell permeable and may use, for example, a QSY7 (diarylyrhodamine) quencher and a BODIPY (bora-diaza-indecene) dye.

  揭示了用于成像含有活性蛋白酶（如半胱氨酸蛋白酶）的细胞的方法和材料。目前的材料包括结合到酶并随后被切割的活性基团探针。切割导致荧光信号的产生，因为去除了一个熄灭基团，当存在于探针上时，会导致改变或无荧光。这些探针使用酰氧甲基酮反应基团，一个或多个氨基酸用于确定特异性，一个荧光团和一个熄灭剂。这些探针具有细胞穿透性，例如，可以使用QSY7（二芳基罗丹明）熄灭剂和BODIPY（硼二氮杂环庚烯）染料。
• Selective Synthesis and Structural Elucidation of <i>S</i>-Acyl- and <i>N</i>-Acylcysteines
  作者：Alan R. Katritzky、Srinivasa R. Tala、Nader E. Abo-Dya、Kapil Gyanda、Bahaa El-Dien M. El-Gendy、Zakaria K. Abdel-Samii、Peter J. Steel

  DOI：10.1021/jo900853s

  日期：2009.9.18

  N-(Acyl)-1H-benzotriazoles 6a−f react with l-cysteine 5 at 20 °C to give exclusively (i) N-acyl-l-cysteines 8a−e in the presence of triethylamine in CH3CN−H2O (3:1), but (ii) S-acyl-l-cysteines 7a−e in CH3CN−H2O (5:1) in the absence of base. Structures 7b, 7d and 8b, 8d are supported by 2D NMR spectroscopic methods including gDQCOSY, gHMQC, gHMBC, and 1H−15N CIGAR-gHMBC experiments. The structure of

  N-（酰基）-1 H-苯并三唑6a - f在20°C下与1-半胱氨酸5反应，仅在CH 3 CN-H中存在三乙胺的情况下仅生成（i）N-酰基-1-半胱氨酸8a - e 2 O（3：1），但（ii）CH 3 CN-H 2 O（5：1）中在不存在碱的情况下的S-酰基-1-半胱氨酸7a - e。结构7b，7d和8b，8d支持2D NMR光谱方法，包括gDQCOSY，gHMQC，gHMBC和1 H - 15 N CIGAR-gHMBC实验。化合物8d的结构也通过单晶X射线衍射来支撑。