2-[(2-甲基丙烷-2-基)氧基羰基氨基]-6-(苯基甲氧羰基氨基)己酸 (4-硝基苯基)酯 | 2389-46-0

• 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
• 中文名称: 2-[(2-甲基丙烷-2-基)氧基羰基氨基]-6-(苯基甲氧羰基氨基)己酸 (4-硝基苯基)酯
• 中文别名: 2-[(2-甲基丙烷-2-基)氧基羰基氨基]-6-(苯基甲氧羰基氨基)己酸(4-硝基苯基)酯；BOC-LYS(Z)-酮P
• 英文名称: N-α-tert-butyloxycarbonyl-N-ε-benzyloxycarbonyl-lysine p-nitrophenyl ester
• 英文别名: Boc-Lys(Z)-ONp；(4-nitrophenyl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoate
• CAS: 2389-46-0
• 化学式: C₂₅H₃₁N₃O₈
• 分子量: 501.536
• InChiKey: FZHFJIODNQYXRK-NRFANRHFSA-N

物化性质

• 熔点：
  89 °C(Solv: ethanol (64-17-5); water (7732-18-5)(1:1))
• 沸点：
  676.9±55.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-[(2-甲基丙烷-2-基)氧基羰基氨基]-6-(苯基甲氧羰基氨基)己酸 (4-硝基苯基)酯 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 23.5h， 生成 L-Lys-ε-(heptadecanoyl)-N1-spermine
  参考文献：
  名称：

  Lysine–spermine conjugates: hydrophobic polyamine amides as potent lipopolysaccharide sequestrants

  摘要：

  Lipopolysaccharides (LPS), otherwise termed `endotoxins' are outer-membrane constituents of Gram-negative bacteria. Lipopolysaccharides play a key role in the pathogenesis of `Septic Shock', a major cause of mortality in the critically ill patient. Therapeutic options aimed at limiting downstream systemic inflammatory processes by targeting lipopolysaccharide do not exist at the present time. We have defined the pharmacophore necessary for small molecules to specifically bind and neutralize LPS and, using animal models of sepsis, have shown that the sequestration of circulatory LPS by small molecules is a therapeutically viable strategy. In this paper, the interactions of a focused library of lysine-spermine conjugates with lipopolysaccharide (LPS) have been characterized. Lysine-spermine conjugates with the epsilon-amino terminus of the lysinyl moiety derivatized with long-chain aliphatic hydrophobic substituents in acyl or alkyl linkage bind and neutralize bacterial lipopolysaccharides, and may be of use in the prevention or treatment of endotoxic shock states. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.038
• 作为产物：
  描述：

  N6-Cbz-L-赖氨酸 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 生成 2-[(2-甲基丙烷-2-基)氧基羰基氨基]-6-(苯基甲氧羰基氨基)己酸 (4-硝基苯基)酯
  参考文献：
  名称：

  Orlowska, Alicja; Drabarek, Stefania, Polish Journal of Chemistry, 1980, vol. 54, # 10, p. 1893 - 1899

  摘要：

  DOI：

文献信息

• Amino acids and peptides. XXVIII. Synthesis of peptide fragments related to eglin c and studies on the relationship between their structure and effects on human leukocyte elastase, cathepsin G and .ALPHA.-chymotrypsin.
  作者：Satoshi TSUBOI、Kazunori NAKABAYASHI、Yoshikazu MATSUMOTO、Naoki TENO、Yuko TSUDA、Yoshio OKADA、Yoko NAGAMATSU、Junichiro YAMAMOTO

  DOI：10.1248/cpb.38.2369

  日期：——

  Various peptide fragments related to eglin c, which consists of 70 amino acid residues, were synthesized by a conventional solution method and their inhibitory effects on leukocyte elastase, cathepsin G and α-chymotrypsin were examined. Among them, H-Arg-Glu-Tyr-Phe-OMe (eglin c 22-25) and H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe (eglin c 41-49) inhibited cathepsin G and α-chymotrypsin but not leukocyte elastase, while H-Thr-Asn-Val-Val-OMe (eglin c 60-63) inhibited leukocyte elastase but not cathepsin G or α-chymotrypsin, although eglin c potently inhibited leukocyte elastase, cathepsin G and α-chymotrypsin. These results indicated that the interaction sites of eglin c with leukocyte elastase, cathepsin G and α-chymotrypsin might be different.

  采用常规的溶液法合成了与来自家蚕血淋巴的抗蛋白酶eglin c（由70个氨基酸残基构成）相关的各种肽片段，并检验了它们对白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶的抑制效应。其中，H-Arg-Glu-Tyr-Phe-OMe（eglin c 22-25）和H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe（eglin c 41-49）能抑制组织蛋白酶G和α-胰凝乳蛋白酶，但不能抑制白细胞弹性蛋白酶，而H-Thr-Asn-Val-Val-OMe（eglin c 60-63）能抑制白细胞弹性蛋白酶，但不能抑制组织蛋白酶G或α-胰凝乳蛋白酶，尽管eglin c对白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶都具有强抑制作用。这些结果提示，eglin c与白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶的相互作用部位可能各不相同。
• NEUROKININ α AND β, SYNTHESIS AND PHARMACOLOGICAL PROPERTIES
  作者：Eisuke Munekata、Masahiro Okada、Sadao Kimura、Yoshiki Sugita、Ichiro Kanazawa、Takayuki Matsudo、Masanori Otsuka

  DOI：10.1246/cl.1984.1013

  日期：1984.6.5

  Two novel neuropeptides, neurokinin α and β, isolated from porcine spinal cord were chemically synthesized by solution method. The amino acid sequences proposed were confirmed to be correct and pharmacological properties of neurokinin peptides were studied.

  通过溶液法化学合成从猪脊髓中分离出的两种新型神经肽，神经激肽α和β。所提出的氨基酸序列被证实是正确的，并研究了神经激肽肽的药理特性。
• Amino Acids and Peptides. XXXIV. Synthesis of Mouse Metallothionein I.(1). Synthesis of Dotriacontapeptide Corresponding to C-Terminal Sequence 30-61 (.ALPHA.-Fragment) of Mouse Metallothionein I and Related Peptides and Examination of Their Heavy Metal-Binding Properties.
  作者：Satoshi MATSUMOTO、Shigeru NAKAYAMA、Yasuhiro NISHIYAMA、Yoshio OKADA、Kyong-Son MIN、Satomi ONOSAKA、Keiichi TANAKA

  DOI：10.1248/cpb.40.2694

  日期：——

  The dotriacontapeptide corresponding to the C-terminal sequence of mouse metallothionein (MT) I and related peptides which contain Cys-X-Cys-Cys (X : amino acid residue except for Cys) sequence were synthesized by the conventional solution method employing the HF deprotection method and their heavy metals (Cd2+, Cu2+ and Cu+)-binding properties were examined.

  合成了对应于小鼠金属硫蛋白 (MT) I C末端序列的三十二肽及相关肽，这些肽包含Cys-X-Cys-Cys（X：除Cys外的氨基酸残基）序列，采用传统溶液法结合HF去保护法，并对它们与重金属（Cd2+、Cu2+和Cu+）的结合特性进行了研究。
• A Simple Synthesis of Imide-Dipeptides
  作者：Chuanlang Zhan、Jiannian Yao、Damei Ke、Xiao Li、Alexander Li

  DOI：10.1055/s-0029-1217167

  日期：——

  We report a simple approach to synthesize a new class of imide-dipeptides. This approach is mild, and the starting materials are the easily accessible amino acid derivatives. The imide-dipeptides were synthesized from the coupling of an amide and a 4-nitrophenyl activating ester of an amino acid. The acidic proton of the first amide was removed by 1 equivalent of n-butyl lithium to afford the corresponding amide anion which then reacted with the activating ester to give the desired imide derivatives.

  我们报告了一种合成新型亚胺二肽的简单方法。这种方法性质温和，起始原料是容易获得的氨基酸衍生物。亚胺二肽是由氨基酸的酰胺和 4-硝基苯基活化酯偶联合成的。第一个酰胺的酸性质子被 1 个等量的正丁基锂去除，得到相应的酰胺阴离子，然后与活化酯反应，得到所需的亚胺衍生物。
• Amino Acids and Peptides. XXXV. Synthesis of Mouse Metallothionein I.(2). Synthesis of a Nonacosapeptide Corresponding to N-Terminal Sequence 1-29(.BETA.-Fragment) of Mouse Metallothionein I and Related Petides and Examination of Their Heavy Metal-Binding Properties.
  作者：Satoshi MATSUMOTO、Yasuhiro NISHIYAMA、Yoshio OKADA、Kyong-Son MIN、Satomi ONOSAKA、Keiichi TANAKA

  DOI：10.1248/cpb.40.2701

  日期：——

  A nonacosapeptide corresponding to the N-terminal sequence 1-29 (beta-fragment) of mouse metallothionein I and related peptides were synthesized by the conventional solution method and their heavy metals (Cu2+, Cu+ and Cd2+)-binding properties were examined. The Cu(2+)- or Cu(+)-binding activities of various peptides were not greatly dependent on the peptide structure, so far as examined, as in the

  通过常规溶液法合成了与小鼠金属硫蛋白I的N端序列1-29（β片段）相对应的非糖肽和相关肽，并研究了它们与重金属（Cu2 +，Cu +和Cd2 +）的结合特性。到目前为止，与N. crassa MT和A. bisporus MT的情况一样，各种肽的Cu（2 +）-或Cu（+）结合活性并不很大地依赖于肽结构。相反，这些肽的Cd（2+）结合活性是相当结构依赖性的。