Tos-Phe-Arg-OH | 112835-65-1

• 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: Tos-Phe-Arg-OH
• 英文别名: [N-(toluene-4-sulfonyl)-L-phenylalanyl=>L-arginine；N-[N-(Toluol-4-sulfonyl)-L-phenylalanyl]-L-arginin；[N-(Toluol-4-sulfonyl)-L-phenylalanyl=>L-arginin；(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2-[(4-methylphenyl)sulfonylamino]-3-phenylpropanoyl]amino]pentanoic acid
• CAS: 112835-65-1
• 化学式: C₂₂H₂₉N₅O₅S
• 分子量: 475.569
• InChiKey: GTDYZKRTCCRNKB-OALUTQOASA-N

物化性质

• 熔点：
  256 °C
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  185
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Tos-Phe-Arg-OH 在 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 Tos-Phe-Arg-Ala-OH hydrochloride
  参考文献：
  名称：

  摘要：

  Boc/Tos-L-Phe-L-Arg-Xaa tripeptides (where Xaa = L-Ala-OBut, L-Ala, or DL-Ala(P)(OC2H5)(2)) were synthesized by conventional methods of peptide synthesis in solution. Special features of their interaction with thrombin and trypsin were studied. Unlike trypsin, thrombin did not catalyze the hydrolysis of the L-Arg-L-Ala(P)(OC2H5)(2) bond. The Tos-L-Phe-L-Arg-DL-Ala(P)(OC2H5)(2) peptide was the most active inhibitor of thrombin among all the compounds studied. The relationship between the structure and inhibitory action of the synthesized peptides is discussed(2).

  DOI：

  10.1023/a:1023976230702
• 作为产物：
  描述：

  N-(对甲苯磺酰)-L-苯丙氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 四氢呋喃 、 三正丁胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 Tos-Phe-Arg-OH
  参考文献：
  名称：

  Synth�se de laL-histidyl-L-ph�nylalanyl-L-arginyl-L-tryptophanyl-glycyl-?-CBO-L-lysyl-L-prolyl-L-valylamide

  摘要：

  AbstractTrityl‐glycyl‐ϵ‐CBO‐L‐lysine is condensed with L‐prolyl‐L‐valine methyl ester and, after amidification and splitting of the trityl group, glycyl‐ϵ‐CBO‐L‐lysyl‐L‐prolyl‐L‐valylamide is obtained. This is condensed with ditrityl‐L‐histidyl‐L‐phenylalanyl‐L‐arginyl‐L‐tryptophane prepared by condensation of ditrityl‐L‐histidyl‐L‐phenylalanine with L‐arginyl‐L‐tryptophane methyl ester and saponification. Dicyclohexyl‐carbodiimide is used as a condensing agent. After splitting off the trityl groups, the final octapeptide, L‐histidyl‐L‐phenylalanyl‐L‐arginyl‐L‐tryptophanyl‐glycyl‐ϵ‐CBO‐L‐lysyl‐L‐prolyl‐L‐valylamide is shown to be optically pure by leucine‐aminopeptidase digestion.

  DOI：

  10.1002/hlca.19580410641

文献信息

• Synth�se de laL-histidyl-L-ph�nylalanyl-L-arginyl-L-tryptophanyl-glycyl-?-CBO-L-lysyl-L-prolyl-L-valylamide
  作者：R. A. Boissonnas、St. Guttmann、R. L. Huguenin、P.-A. Jaquenoud、Ed. Sandrin

  DOI：10.1002/hlca.19580410641

  日期：——

  AbstractTrityl‐glycyl‐ϵ‐CBO‐L‐lysine is condensed with L‐prolyl‐L‐valine methyl ester and, after amidification and splitting of the trityl group, glycyl‐ϵ‐CBO‐L‐lysyl‐L‐prolyl‐L‐valylamide is obtained. This is condensed with ditrityl‐L‐histidyl‐L‐phenylalanyl‐L‐arginyl‐L‐tryptophane prepared by condensation of ditrityl‐L‐histidyl‐L‐phenylalanine with L‐arginyl‐L‐tryptophane methyl ester and saponification. Dicyclohexyl‐carbodiimide is used as a condensing agent. After splitting off the trityl groups, the final octapeptide, L‐histidyl‐L‐phenylalanyl‐L‐arginyl‐L‐tryptophanyl‐glycyl‐ϵ‐CBO‐L‐lysyl‐L‐prolyl‐L‐valylamide is shown to be optically pure by leucine‐aminopeptidase digestion.
• ——
  作者：S. A. Poyarkova

  DOI：10.1023/a:1023976230702

  日期：——

  Boc/Tos-L-Phe-L-Arg-Xaa tripeptides (where Xaa = L-Ala-OBut, L-Ala, or DL-Ala(P)(OC2H5)(2)) were synthesized by conventional methods of peptide synthesis in solution. Special features of their interaction with thrombin and trypsin were studied. Unlike trypsin, thrombin did not catalyze the hydrolysis of the L-Arg-L-Ala(P)(OC2H5)(2) bond. The Tos-L-Phe-L-Arg-DL-Ala(P)(OC2H5)(2) peptide was the most active inhibitor of thrombin among all the compounds studied. The relationship between the structure and inhibitory action of the synthesized peptides is discussed(2).