Nα-Boc-Nτ-Ts-histidine | 95730-55-5

• 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: Nα-Boc-Nτ-Ts-histidine
• 英文别名: Boc-His(Tos)；Boc-His(Tos)-OH；(2S)-3-[3-(4-methylphenyl)sulfonylimidazol-4-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 95730-55-5
• 化学式: C₁₈H₂₃N₃O₆S
• 分子量: 409.463
• InChiKey: MTZSTFRHYLPNIF-HNNXBMFYSA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  127.59
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Nα-Boc-Nτ-Ts-histidine 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-{1-propenylcarbamoyl-2-[3-(toluene-4-sulfonyl)-3H-imidazol-4-yl]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Self-Selection in Olefin Cross-Metathesis:  The Effect of Remote Functionality

  摘要：

  [GRAPHICS]Olefin cross-metathesis (CM) is potentially an attractive method for generating dynamic combinatorial libraries (DCLs). In order for the CM reaction to be useful for DCL production, the course of the reaction and product distribution must be relatively insensitive to functionality remote from the reacting centers. We report on the CM of a series of allyl- and homoallylamides that are strongly dependent on remote functionality. This includes an unusual example of a cis-selective CM.

  DOI：

  10.1021/ol047361u
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三甲基氢氧化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 9.0h， 以93%的产率得到Nα-Boc-Nτ-Ts-histidine
  参考文献：
  名称：

  氢氧化三甲基锡选择性地分离Merrifield，PAM和Wang树脂中Boc保护的氨基酸和肽

  摘要：

  我们描述了一种新的非酸解性和非亲核性方法的发展，该方法用于通过三甲基锡氢氧化物选择性地切割氨基酸和二肽在与酯合成中常用的树脂连接的苄基酯键处进行选择性切割。

  DOI：

  10.1016/s0040-4020(98)00805-9

文献信息

• Synthesis of the Five Peptide Derivatives Needed to Build the Sequence Corresponding to 1–30 of Human Epidermal Growth Factor (h-EGF)
  作者：Song Yuh Shin、Yukihiko Kaburaki、Masanori Watanabe、Eisuke Munekata

  DOI：10.1271/bbb.56.399

  日期：1992.1

  For the classical solution synthesis of human epidermal growth factor (h-EGF), five protected peptide derivatives, Boc-Leu-Asp(OcHex)-Lys(Cl-Z)-Tyr(Br-Z)-Ala-OH (5), Boc-Val-Cys(MeBzl)-Met-Tyr(Br-Z)-Ile-Glu(OcHex)-Ala-OH (12), Boc-Tyr(Br-Z)-Cys(MeBzl)-Leu-His-Asp(OcHex)-Gly-OH (18), Boc-Cys(MeBzl)-Pro-Leu-Ser(Bzl)-His-Asp(OcHex)-Gly-O H (23) and Boc-Asn-Ser(Bzl)-Asp(OcHex)-Ser(Bzl)-Glu(OcHex)-OH (28) were synthesized to build up the sequence corresponding to 1–30.

  对于人表皮生长因子（h-EGF）的经典合成解决方案，合成了五种保护性肽衍生物，即Boc-Leu-Asp(OcHex)-Lys(Cl-Z)-Tyr(Br-Z)-Ala-OH（5），Boc-Val-Cys(MeBzl)-Met-Tyr(Br-Z)-Ile-Glu(OcHex)-Ala-OH（12），Boc-Tyr(Br-Z)-Cys(MeBzl)-Leu-His-Asp(OcHex)-Gly-OH（18），Boc-Cys(MeBzl)-Pro-Leu-Ser(Bzl)-His-Asp(OcHex)-Gly-O H（23）和Boc-Asn-Ser(Bzl)-Asp(OcHex)-Ser(Bzl)-Glu(OcHex)-OH（28），以构建对应于1-30的序列。
• The Influence of Protecting Groups on the<i>β</i>-Sheet-Structure Stability of Protected Peptides
  作者：Sho-kichi Oh-uchi、Jin-Shik Lee、Mitsuaki Narita

  DOI：10.1246/bcsj.69.1303

  日期：1996.5

  The influence of protecting groups on the β-sheet-structure stability of protected peptides was studied in organic solvents. α-Amino groups, carboxyl groups, and side-chain functional groups of model peptides were protected by availably used protecting groups. The difference between the solubilities of model peptides was investigated by the solvent-titration method using infrared (IR) absorption spectra

  在有机溶剂中研究了保护基团对受保护肽的 β-折叠结构稳定性的影响。模型肽的α-氨基、羧基和侧链官能团被可用的保护基团保护。通过使用红外 (IR) 吸收光谱的溶剂滴定法研究模型肽的溶解度之间的差异。除了 Npys、Mts 和 Z2 之外，每个保护基团的 β-折叠结构稳定电位 (SPβ) 表现出相似的行为。结果表明，被保护肽的值几乎与其保护基的种类无关。
• 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。
• Renin inhibitors. Design of angiotensinogen transition-state analogs containing novel (2R,3R,4R,5S)-5-amino-3,4-dihydroxy-2-isopropyl-7-methyloctanoic acid
  作者：Suvit Thaisrivongs、Donald T. Pals、Lisa T. Kroll、Steve R. Turner、Fu Son Han

  DOI：10.1021/jm00389a004

  日期：1987.6

  5S)-5-amino-3,4-dihydroxy-2-isopropyl-7-methyloctanoic acid residue at the scissile site are shown to be potent inhibitors of human plasma renin. The glycol moiety in this novel acid, dihydroxyethylene isostere, is suggested to act as a transition-state analogue and mimics the tetrahedral intermediate formed during the enzyme-catalyzed hydrolysis of the peptidic bond.

  2（R）-[5（R）-[1（S）-[（叔丁氧羰基氨基）氨基] -3-甲基丁基] -2,2-二甲基-4（R-二氧戊环）-的高立体选择性合成描述了3-甲基丁酸。这是一种适当保护的羧酸，可用作制备肾素抑制肽的中间体。血管紧张素原类似物如肽IX和X在易裂位点含有二肽等排物（2R，3R，4R，5S）-5-氨基-3,4-二羟基-2-异丙基-7-甲基辛酸残基人血浆肾素的有效抑制剂。该新型酸二羟基乙烯等排物中的二醇部分被建议充当过渡态类似物，并模仿在酶催化的肽键水解过程中形成的四面体中间体。
• Semisynthesis and biological activity of aminoacyl triesters of squamocin, an annonaceous acetogenin
  作者：Romain A. Duval、Philippe Duret、Guy Lewin、Eva Peris、Reynald Hocquemiller

  DOI：10.1016/j.bmc.2005.03.029

  日期：2005.6

  A number of aminoacyl triesters of squamocin 1, a cytotoxic acetogenin isolated from the seeds of Annona reticulata, have been synthesized in two to three steps from protected (L)-aminoacids and squamocin 1 using standard coupling/deprotection procedures. These semisynthetic analogs were tested on submitochondrial particles (SMP) for their complex I inhibitory activities, and against KB 3-1 cells in vitro. All triesters derivatives exhibited a complete extinction of activity at the enzymatic level, correlated to a reduced though modulated cytotoxicity in comparison with squamocin 1. This activity can apparently be considered as a function of the amphipathy of the analogs, the more amphiphilic ones being the more cytotoxic. (c) 2005 Elsevier Ltd. All rights reserved.