N-Alpha-Z-N-ω-tosyl-L-精氨酸环己胺盐 | 13650-38-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-Alpha-Z-N-ω-tosyl-L-精氨酸环己胺盐
• 中文别名: NALPHA-苄氧羰基-NOMEGA-对甲苯磺酰基-L-精氨酸
• 英文名称: Z-Arg(Tos)-OH
• 英文别名: (2S)-5-[amino-[(4-methylphenyl)sulfonylamino]methylidene]azaniumyl-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 13650-38-9
• 化学式: C₂₁H₂₆N₄O₆S
• mdl: MFCD00077010
• 分子量: 462.527
• InChiKey: BHQRCFPZYISVMF-SFHVURJKSA-N

物化性质

• 熔点：
  86-88℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-Alpha-Z-N-ω-tosyl-L-精氨酸环己胺盐 在 三氟甲磺酸三甲基硅酯 、 茴香硫醚 作用下， 以 三氟乙酸 为溶剂， 反应 0.5h， 以62.1%的产率得到L-精氨酸
  参考文献：
  名称：

  蛋白质化学合成的新策略

  摘要：

  对于蛋白质的化学合成，描述了通过组合硬酸，三甲基甲硅烷基三氟甲磺酸盐和软亲核试剂例如硫代苯甲醚进行的有效脱保护程序。对于二硫键的形成，提出了两种新的方法。一种通过三氟乙酸al（III）氧化而另一种通过酸催化反应进行，涉及S取代的半胱氨酸亚砜。

  DOI：

  10.1016/s0040-4020(01)86118-4
• 作为产物：
  描述：

  L-精氨酸 生成 N-Alpha-Z-N-ω-tosyl-L-精氨酸环己胺盐
  参考文献：
  名称：

  13C-NMR-Studien von gesch�tzten Aminos�uren

  摘要：

  DOI：

  10.1007/bf00910279

文献信息

• Synthesis and SAR Study of Novel Peptide Aldehydes as Inhibitors of 20S Proteasome
  作者：Yuheng Ma、Bo Xu、Yuan Fang、Zhenjun Yang、Jingrong Cui、Liangren Zhang、Lihe Zhang

  DOI：10.3390/molecules16097551

  日期：——

  (1) and 20S proteasomes, a new series of peptide aldehyde derivatives were designed and synthesized. Their ability to inhibit 20S proteasome was assayed. Among them, Cbz-Glu(OtBu)-Phe-Leucinal (3c), Cbz-Glu(OtBu)-Leu-Leucinal (3d), and Boc-Ser(OBzl)-Leu-Leucinal (3o) exhibited the most activity, which represented an order of magnitude enhancement compared with MG132 (2). The covalent docking protocol

  在分析MG101(1)和20S蛋白酶体晶体结构的基础上，设计合成了一系列新的肽醛衍生物。测定了它们抑制 20S 蛋白酶体的能力。其中，Cbz-Glu(OtBu)-Phe-Leucinal (3c)、Cbz-Glu(OtBu)-Leu-Leucinal (3d) 和 Boc-Ser(OBzl)-Leu-Leucinal (3o) 的活性最强，与 MG132 (2) 相比，这代表了一个数量级的增强。共价对接协议用于探索结合模式。讨论了肽醛抑制剂的构效关系。
• Studies on peptides. CLII. Hard acid deprotecting procedure for peptide synthesis.
  作者：NOBUTAKA FUJII、AKIRA OTAKA、OSAMU IKEMURA、MIKA HATANO、AKIRA OKAMACHI、SUSUMU FUNAKOSHI、MITSUYA SAKURAI、TAKAYUKI SHIOIRI、HARUAKI YAJIMA

  DOI：10.1248/cpb.35.3447

  日期：——

  The use of trimethylsilyl trifluoromethanesulfonate as a peptide deprotecting reagent was examined, together with the role of soft bases employed. A new deprotecting procedure based on the hard acid principle is presented.

  考察了使用三甲基硅烷三氟甲磺酸酯作为肽脱保护试剂的效果，并探讨了软碱的作用。基于硬酸原理，提出了一种新的脱保护程序。
• Amino Acids and Peptides. XXV. Preparation of Fibronectin-Related Peptide Poly(ethylene glycol) Hybrids and Their Inhibitory Effect on Experimental Metastasis.
  作者：Koichi KAWASAKI、Machiko NAMIKAWA、Yuko YAMASHIRO、Yuji IWAI、Takao HAMA、Yasuo TSUTSUMI、Susumu YAMAMOTO、Shinsaku NAKAGAWA、Tadanori MAYUMI

  DOI：10.1248/cpb.43.2133

  日期：——

  Hybrids of fibronectin-related peptides [Arg-Gly-Asp (RGD), Arg-Gly-Asp-Ser (RGDS)] and poly(ethylene glycol) (PEG) were prepared and their inhibitory effects on experimental metastasis in mice were examined. The inhibitory effect of RGD was markedly potentiated by hybrid formation with poly(ethylene glycol) #6000. As to inhibitory effect, RGD was more potent than RGDS and RGD PEG hybrids were superior to RGDS PEG hybrids. Hybrid formation with PEG #6000 was more effective than that with PEG #4000.

  将整合素连接肽[精-甘-天冬 (RGD)，精-甘-天冬-丝 (RGDS)] 与聚乙二醇 (PEG) 的缀合物制备出来，并研究了它们对小鼠实验性转移的抑制作用。与聚乙二醇 #6000 形成的缀合物显著增强了 RGD 的抑制效果。在抑制作用方面，RGD 比 RGDS 更强，而 RGD PEG 缀合物优于 RGDS PEG 缀合物。与 PEG #4000 相比，与 PEG #6000 形成的缀合物效果更佳。
• Studies on secretin. I. Synthesis of completely protected secretin.
  作者：MIKIO UCHIYAMA、TAKASHI SATO、HIROSHI YOSHINO、YUTAKA TSUCHIYA、TOSHIRO TSUDA、MASAYUKI KONISHI、MASAHIKO TSUJII、YOSHIHIKO HISATAKE、ATSUSHI KOIWA

  DOI：10.1248/cpb.33.1990

  日期：——

  In order to establish a new process for large-scale production of highly purified secretin, a synthesis based on a new strategy was investigated. A maximal protection method applying the HF deprotecting procedure in the final stage was employed. Six small protected fragments (2-6, 7-10, 11-13, 14-17, 18-22, 23-27) were each prepared by stepwise chain elongation. Thereafter, three protected fragments (1-10, 11-17, 18-27) were synthesized from them, and assembled to prepare the protected secretin. The optical purity of the product after each fragment condensation was checked by high performance liquid chromatography. Completely protected secretin having a high degree of chemical and optical homogeneity was obtained.

  为了建立大规模生产高纯度胰泌素的新工艺，研究人员研究了一种基于新策略的合成方法。在最后阶段采用了高频脱保护程序的最大保护方法。通过分步链延长法分别制备了六个小的受保护片段（2-6、7-10、11-13、14-17、18-22、23-27）。然后，由它们合成三个受保护的片段（1-10、11-17、18-27），并组装成受保护的泌乳素。高效液相色谱法检测了每个片段缩合后产物的光学纯度。得到的完全保护泌乳素具有高度的化学和光学均一性。
• Synthesis of a Partial Sequence of Proinsulin Using the A-Chain of Natural Insulin. IV. Synthesis of a Peptide Corresponding to Positions 31–81 of Bovine Proinsulin
  作者：Hiroko Aiba、Yasutsugu Shimonishi

  DOI：10.1246/bcsj.53.201

  日期：1980.1

  For the synthesis of bovine proinsulin, the S-sulfonate of the Ala–Leu–Glu–Leu–Ala–Gly–Gly–Pro–Gly–Ala–Gly–Gly–Leu–Glu–Gly–Pro–Pro–Gln–Lys[Z(2-Cl)]–Arg–A-chain, which corresponds to positions 41–81 of bovine proinsulin, was coupled with Boc–Arg(Tos)–Arg(Tos)–Glu(OBut)–Val–Glu(OBut)–Gly–Pro–Gln–Val–Gly–N3. The S-sulfonate of the Arg(Tos)–Arg(Tos)–Glu–Val–Glu–Gly–Pro–Gln–Val–Gly–Ala–Leu–Glu–Leu–Ala–Gly–Gly–Pro–Gly–Ala–Gly–Gly–Leu–Glu–Gly–Pro–Pro–Gln–Lys[Z(2-Cl)]–Arg–A-chain, correspoding to positions 31–81 of bovine proinsulin, was obtained in a pure form by removal of the protecting groups from the coupled product and chromatography on QAE-Sephadex A-25.

  Boc-Arg(Tos)-Arg(Tos)-Glu(OBut)-Val-Glu(OBut)-Gly-Pro-Gln-Val-Gly-N3 与牛脯胰岛素的 41-81 位相对应。通过去除偶联产物中的保护基团并在 QAE-Sephadex A-25 上进行色谱分析，得到了 Arg（Tos）-Arg（Tos）-Glu-Val-Glu-Gly-Pro-Gln-Val-Gly-Ala-Leu-Glu-Leu-Ala-Gly-Gly-Pro-Gla-Gly-Leu-Glu-Gly-Pro-Gln-Lys[Z(2-Cl)]-Arg-A 链的 S-磺酸盐纯品，它对应于牛脯脯氨酸的 31-81 位。