N-(苄氧羰基)-L-丙氨酸对硝基苯酯 | 1168-87-2

• 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: N-(苄氧羰基)-L-丙氨酸对硝基苯酯
• 英文名称: Z-Ala-ONp
• 英文别名: benzyloxycarbonylalanine p-nitrophenyl ester；Cbz-Ala-ONp；(4-nitrophenyl) (2S)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 1168-87-2
• 化学式: C₁₇H₁₆N₂O₆
• mdl: MFCD00038118
• 分子量: 344.324
• InChiKey: SXWWICLSRXPNNW-LBPRGKRZSA-N

物化性质

• 熔点：
  78-79℃
• 沸点：
  542.7±45.0 °C(Predicted)
• 密度：
  1.315

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.176
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(苄氧羰基)-L-丙氨酸对硝基苯酯 在 γ-环糊精 作用下， 以 乙腈 为溶剂， 生成 苄氧羰基-L-丙氨酸
  参考文献：
  名称：

  具有明显立体选择性的环糊精介导的氨基酸酯的脱酰作用。

  摘要：

  关于由α-，β-和γ-环糊精（CyDs）介导的ZD（L）-氨基酸酯（N-（苄氧基羰基）-D（L）-氨基酸对硝基苯酯）的水解（脱酰）作用，观察到Ala底物与γ-CyD脱酰基的对映选择性非常高（L / D = 9.0）。基于Michaelis-Menten原理的动力学结果表明，对映选择性应主要源自γ-CyD-底物（1：1）复合物形成后底物的脱酰基过程。还介绍了对包合物的计算机建模（分子力学）研究。

  DOI：

  10.1248/cpb.50.1283
• 作为产物：
  描述：

  对硝基苯酚 在 喹啉 作用下， 生成 N-(苄氧羰基)-L-丙氨酸对硝基苯酯
  参考文献：
  名称：

  N-保护的氨基酸的活化酯的合成

  摘要：

  描述了一种用于合成N-保护的氨基酸的活化酯的简化方法。合成通过碳酸叔丁酯或碳酸苄酯的各种活性酯的氨解进行，并且在该过程中置换的离去基团通过将二环己基碳二亚胺添加到反应混合物中而重新结合，从而得到所需化合物。

  DOI：

  10.1039/j39670000689

文献信息

• Synthesis and structure of prolinal-containing peptides, and their use as specific inhibitors of prolyl endopeptidases.
  作者：MAKOTO NISHIKATA、HIDEYOSHI YOKOSAWA、SHIN-ICHI ISHII

  DOI：10.1248/cpb.34.2931

  日期：——

  Peptide aldehydes are potent inhibitors of serine and cysteine proteases. In the present work, N-benzyloxycarbonyl (Z) dipeptides containing prolinal at the carboxyl terminus were syntheized as inhibitors of prolyl endopeptidases. Since no aldehyde proton was detected by proton nuclear magnetic resonance (1H-NMR) spectrometry, a cyclic structure was proposed for these peptides. Compounds with a Z-L-X-L-prolinal structure were strong inhibitors of prolyl endopeptidases from the ascidian, Halocynthia roretzi, and Flavobacterium meningosepticum. The potency was in the order of Z-L-Val-L-prolinal≃Z-L-Ile-L-prolinal>Z-L-Phe-L-prolinal>Z-L-Ala-L-prolinal with IC50 values of 10-8-10-6 M order for both enzymes. Conversion of the aldehyde into an alcohol or an acid moiety resulted in a considerable decrease in the inhibitory activity. The diastereomers of Z-L-Phe-L-prolinal were much less inhibitory. This result is not compatible with the reported stereospecifity of the Flavobacterium enzyme for its substrated [T. Yoshimoto, R. Walter and D. Tsuru, J. Biol. Chem., 255, 4786 (1980)]. This implies that the open species binds preferentially to the enzyme active site.

  肽醛是丝氨酸和半胱氨酸蛋白酶的强效抑制剂。在本研究工作中，合成了含羧基末端脯氨醛的N-苄氧羰基（Z）二肽，作为脯氨酰内肽酶的抑制剂。由于通过质子核磁共振（1H-NMR）光谱法未检测到醛质子，因此为这些肽提出了一个环状结构。具有Z-L-X-L-脯氨醛结构的化合物是海鞘Halocynthia roretzi和黄杆菌Flavobacterium meningosepticum的脯氨酰内肽酶的强效抑制剂。其效力顺序为Z-L-Val-L-脯氨醛≈Z-L-Ile-L-脯氨醛>Z-L-Phe-L-脯氨醛>Z-L-Ala-L-脯氨醛，IC50值为10-8-10-6 M，对两种酶均有效。将醛转化为醇或酸部分会导致抑制活性显著降低。Z-L-Phe-L-脯氨醛的差向异构体抑制作用较弱。这一结果与黄杆菌酶对其底物的报道立体特异性不一致。这表明开放型物种优先结合到酶活性位点。
• Peptide Synthesis in Aqueous Solution. I. Application of<i>p</i>-Dialkylsulfoniophenols as a Water-Soluble Coupling Reagent
  作者：Katsushige Kouge、Tatsuya Koizumi、Hideo Okai、Tetsuo Kato

  DOI：10.1246/bcsj.60.2409

  日期：1987.7

  found to be an excellent coupling reagent having a water-soluble property and a high reactivity; it worked as satisfactory as usual active esters in regard to the reactivity, product purity, and racemization. The marked advantage of the HODMSP·MeSO4− active ester method was the fact that bifunctional residues such as Arg, Lys, Cys, and Tyr could be selectively acylated when the pH of the reaction mixture

  发现(对羟基苯基)二甲基锍甲基硫酸盐(HODMSP·MeSO4-)是一种优良的偶联剂，具有水溶性和高反应性；在反应性、产品纯度和外消旋化方面，它与通常的活性酯一样令人满意。HODMSP·MeSO4-活性酯法的显着优势在于，当反应混合物的pH值得到控制时，双功能残基如Arg、Lys、Cys和Tyr可以被选择性地酰化。通过这种新的活性酯方法合成了软体动物神经肽 FMRFamide（Phe-Met-Arg-Phe-NH2），以评估该方法在涉及肽合成的进一步应用中的应用。
• PEPTIDES WITH CYTOPROTECTIVE ACTIVITY
  申请人：Zamerton Holdings Limited

  公开号：EP2963052A2

  公开（公告）日：2016-01-06

  This invention is related to medicine and concerns peptides with cytoprotective activity selected from a group that includes Ac-Asp-Glu-OH, H-Asp-Glu-OCH3, H-Asp-Glu-NH - CH2-CH3, H-Val-Asp-Glu-OH, H-Leu-Asp- Glu-OH and H-Ala-Asp-Glu-Arg-OH, Ala-Asp-Glu, Lys-Asp-Glu and Asp-Glu-Gly, with the peptides remaining chemically stable in storage. Also proposed is a pharmaceutical composition containing effective quantities of peptides selected from a group that includes Ac-Asp-Glu-OH, H-Asp-Glu-OCH3, H-Asp-Glu-NH - CH2-CH3, H-Val-Asp-Glu-OH, H-Leu-Asp- Glu-OH and H-Ala-Asp-Glu-Arg-OH, Ala-Asp-Glu, Lys-Asp-Glu or Asp-Glu-Gly. The pronounced cytoprotective effect makes it possible to use the pharmaceutical composition in the food, cosmetological and pharmaceutical industries.

  这项发明涉及医学，涉及具有细胞保护活性的肽，所选肽包括Ac-Asp-Glu-OH、H-Asp-Glu-O 、H-Asp-Glu-NH-CH2-CH3、H-Val-Asp-Glu-OH、H-Leu-Asp-Glu-OH和H-Ala-Asp-Glu-Arg-OH、Ala-Asp-Glu、Lys-Asp-Glu和Asp-Glu-Gly，这些肽在储存中保持化学稳定。还提出了一种含有所选肽的药物组合物，该组合物包括Ac-Asp-Glu-OH、H-Asp-Glu-O 、H-Asp-Glu-NH- - 、H-Val-Asp-Glu-OH、H-Leu-Asp-Glu-OH和H-Ala-Asp-Glu-Arg-OH、Ala-Asp-Glu、Lys-Asp-Glu或Asp-Glu-Gly。显著的细胞保护作用使得可以将该药物组合物用于食品、化妆品和制药行业。
• Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of β-Keto Thioethers
  作者：Rafael M. P. Dias、Antonio C. B. Burtoloso

  DOI：10.1021/acs.orglett.6b01470

  日期：2016.6.17

  Insertion of sulfoxonium ylides into the S–H bond of aryl thiols without the need for a catalyst is demonstrated, furnishing β-keto thioethers in excellent yield in most cases. The method overcomes traditional syntheses that employ metal catalysts in combination with diazo compounds or toxic and hard-prepared haloketones. The experimental setup consists of mixing the reagents in acetonitrile at room

  已证明不需要催化剂就可以将亚砜基烷基化物插入芳基硫醇的S–H键中，在大多数情况下，都能以优异的产率提供β-酮硫醚。该方法克服了传统的合成方法，该方法采用金属催化剂与重氮化合物或有毒和难制备的卤代酮结合使用。实验设置包括在室温下将试剂在乙腈中混合。附加的实验以及动力学同位素效应研究为该反应的机理提供了一些见识。
• Polypeptides. Part II. A “hydrazino-peptide” analogue of norophthalmic acid amide
  作者：P. H. Bentley、J. S. Morley

  DOI：10.1039/j39660000060

  日期：——

  The synthesis is described of an analogue (II) of norophthalmic acid amide (I), wherein the amide bond connecting the alanyl and glycyl residues is replaced by a hydrazide bond.

  描述了邻邻苯二甲酸酰胺（I）的类似物（II）的合成，其中连接丙氨酰基和甘氨酰基残基的酰胺键被酰肼键代替。