Boc-Cys(MBzl)-ONp | 53843-86-0

• 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: Boc-Cys(MBzl)-ONp
• 英文别名: N-(t-butoxycarbonyl)-S-p-methoxybenzyl-l-cysteine p-nitrophenyl ester；(4-nitrophenyl) (2R)-3-[(4-methoxyphenyl)methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 53843-86-0
• 化学式: C₂₂H₂₆N₂O₇S
• 分子量: 462.524
• InChiKey: CDUOSRYRVBJSIG-IBGZPJMESA-N

物化性质

• 沸点：
  636.1±55.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Boc-Cys(MBzl)-ONp 在 一水合肼 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 Boc-Cys(MBzl)-Val-Thr-N3
  参考文献：
  名称：

  合成一个37个残基的肽酰胺，该肽酰胺对应于大鼠降钙素基因相关肽（α-rCGRP）的α-形式的整个氨基酸序列。

  摘要：

  采用传统的溶液法合成了与大鼠降钙素基因相关肽（α-rCGRP）的整个氨基酸序列相对应的七胜肽酰胺。用 1 M 三氟甲磺酸-硫代苯甲醚-三氟乙酸去除所有保护基团，然后对去保护基团的肽进行氧化反应以形成分子内二硫键。经 Sephadex G-50 凝胶过滤纯化后，再经反相高效液相色谱纯化，就得到了高度纯化的合成 α-rCGRP 样品。在抑制合成人甲状旁腺激素（1-34）刺激的骨 45Ca 释放方面，合成 α-rCGRP 与合成人 CGRP 具有同样的活性。

  DOI：

  10.1248/cpb.35.60

文献信息

• Synthesis of the heptadecapeptide corresponding to the entire amino acid sequence of salmon melanin-concentrating hormone (MCH).
  作者：KENJI OKAMOTO、KOICHI YASUMURA、KAZUYOSHI FUJITANI、YOSHIAKI KISO、HIROSHI KAWAUCHI、ICHIRO KAWAZOE、HARUAKI YAJIMA

  DOI：10.1248/cpb.32.2963

  日期：——

  The heptadecapeptide corresponding to the entire amino acid sequence of melaninconcentrating hormone (MCH), isolated from chum salmon pituitaries, was synthesized by successive condensation of four peptide fragments and the N-terminal amino acid, i. e., Boc-(14-17)-OBzl, Boc-(9-13)-OH, Boc-(5-8)-NHNH2, Boc-(2-4)-NHNH2 and Boc-Asp (OBzl)-OH, followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid (TFA) and disulfide formation through the S-sulfonate. When melanin-concentrating activity was measured on a tilapia scale, the minimum effective concentration of the synthetic peptide was equivalent to that of natural salmon MCH (1nM).

  从大麻哈鱼脑下垂体中分离出的、与促黑激素（MCH）整个氨基酸序列相对应的十七肽，是通过四个肽片段和N-端氨基酸，即Boc-(14-17)-OBzl、Boc-(9-13)-OH、Boc-(5-8)-NHNH2、Boc-(2-4)-NHNH2 和Boc-Asp(OBzl)-OH，依次缩合合成，随后用三氟乙酸（TFA）中的1M三氟甲磺酸-硫茴处理，通过S-磺酸酯形成二硫键并去保护。当在罗非鱼身上测量促黑活性时，合成肽的最小有效浓度与天然大麻哈鱼MCH的浓度（1nM）相当。
• Amino acids and peptides. XXVII. Synthesis of phytochelatin-related peptides and examination of their heavy metal-binding properties.
  作者：Yoshikazu MATSUMOTO、Yoshio OKADA、Kyong-Son MIN、Satomi ONOSAKA、Keiichi Tanaka

  DOI：10.1248/cpb.38.2364

  日期：——

  Phytochelatin (PC)-related peptides were prepared by a conventional solution method and their heavy metal-binding properties were examined. Different from the Cu2+ and Cu+ -binding properties of metallothionein (MT)-related peptides, the Cu2+ and Cu+ -binding properties of PC-related peptides were fairly dependent on structure. It is of interest that gamma-Glu-Cys-Gly (glutathione) exhibited quite

  通过常规溶液法制备植物螯合素（PC）相关肽，并检查其重金属结合特性。与金属硫蛋白（MT）相关肽的Cu2 +和Cu +结合特性不同，PC相关肽的Cu2 +和Cu +结合特性完全取决于结构。有趣的是，γ-Glu-Cys-Gly（谷胱甘肽）表现出与其他PC相关肽完全不同的Cu2 +和Cu +结合特性，其结合能力与MT相关肽相当。谷胱甘肽的Cd2 +结合特性与Cys相似，PC相关肽的Cd2 +结合能力与γ-Glu-Cys肽单元的增加成比例地增加。
• Amino acids and peptides. IX. Synthesis of cysteine-containing peptide fragments related to human hepatic metallothionein II (hMT II) and determination of their heavy metal-binding properties.
  作者：NORIYA OHTA、YOSHIO OKADA、KEIICHI TANAKA

  DOI：10.1248/cpb.31.3094

  日期：——

  Eight kinds of cysteine-containing peptides related to human hepatic metallothionein were synthesized by conventional methods. The metal-binding properties of these peptides with Zn2+ and Cd2+ were indicated by an increase of ultraviolet absorbance resulting from mercaptide formation. The Cd-binding activities of various peptides obtained here were assessed by measuring the increase in absorbance of mercaptide at 250 nm as a function of the concentration of Cd. The binding abilities of the peptides with Cd differed substancially.

  采用传统方法合成了八种与人类肝脏金属硫蛋白相关的含半胱氨酸肽。这些肽与 Zn2+ 和 Cd2+ 的金属结合特性是通过巯基的形成导致紫外吸光度的增加来显示的。通过测量 250 纳米波长处硫醇吸光度的增加与镉浓度的函数关系，评估了在此获得的各种多肽的镉结合活性。肽与镉的结合能力有很大差异。
• Amino acids and peptides. VIII. Synthesis of a hexacosapeptide corresponding to the C-terminal sequence 36-61 of human metallothionein II (hMT II) and determination of its heavy metal binding activity.
  作者：NORIYA OHTA、YOSHIO OKADA、KEIICHI TANAKA

  DOI：10.1248/cpb.31.1885

  日期：——

  A C-terminal hexacosapeptide corresponding to residues 36-61 of human liver metallothionein (hMT II) was synthesized by the fragment condensation method using the azide procedure. Protecting groups were removed by the methanesulfonic acid (MSA) method or hydrogen fluoride (HF) method to give the desired peptide. The binding ability of this peptide with Cd and Zn was examined by measuring the absorbance in the ultraviolet region (200-260 nm) as a function of heavy metal concentration and by the gel-filtration method. The heavy metal-binding behavior of this peptide is quite similar to that of thionein.

  使用叠氮化物程序通过片段缩合法合成了对应于人肝金属硫蛋白(hMT II)的残基36-61的C端六肽。通过甲磺酸（MSA）法或氟化氢（HF）法去除保护基，得到所需的肽。通过测量紫外区（200-260 nm）的吸光度作为重金属浓度的函数并通过凝胶过滤方法检查该肽与 Cd 和 Zn 的结合能力。该肽的重金属结合行为与硫因非常相似。
• Amino acids and peptides. XXVI. Synthesis of Agaricus bisporus metallothionein and related peptides and examination of their heavy metal-binding properties.
  作者：Yasuhiro NISHIYAMA、Sigeru NAKAYAMA、Yoshio OKADA、Kyong-Son MIN、Satomi ONOSAKA、Keiichi TANAKA

  DOI：10.1248/cpb.38.2112

  日期：——

  pentacosapeptide corresponding to the entire amino acid sequence of Agaricus bisporus metallothionein (MT) and related cysteine-containing peptides were prepared by the conventional solution method and their heavy metal-binding properties were examined. The Cu2(+)- or Cu(+)-binding activities of various peptides were not greatly dependent on the peptide structure, so far as examined, although the pentacosapeptide

  通过常规溶液法制备了与双孢蘑菇金属硫蛋白（MT）的整个氨基酸序列相对应的五肽和相关的含半胱氨酸的肽，并检查了它们的重金属结合特性。到目前为止，各种肽的Cu2 +或Cu（+）结合活性并不很大地依赖于肽的结构，尽管五糖肽A. bisporus MT的结合活性比其他肽稍高。相反，这些肽的Cd2（+）结合活性是相当结构依赖性的。