H-Arg(Mts)-OH | 58810-06-3

• 分子结构分类: 有机化合物
• 英文名称: H-Arg(Mts)-OH
• 英文别名: N6-Mesitylen-2-sulfonyl-arginin；(2S)-2-amino-5-[[amino-[(2,4,6-trimethylphenyl)sulfonylamino]methylidene]amino]pentanoic acid
• CAS: 58810-06-3
• 化学式: C₁₅H₂₄N₄O₄S
• 分子量: 356.446
• InChiKey: JZLDAECPZATNDI-LBPRGKRZSA-N

物化性质

• 沸点：
  550.2±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  145.37
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  H-Arg(Mts)-OH 在 N-甲基吗啉 、 ethandithiol 、 三氟甲磺酸 、 茴香硫醚 、 thermolysin 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 7.0h， 生成 H-Phe-Met-Arg-Leu-NH2
  参考文献：
  名称：

  Thermolysin-catalyzed synthesis of peptide amides.

  摘要：

  研究了热溶解酶在各种氨基酸酰胺和受保护或未受保护的肽之间的酶促缩合作用。作为模型，制备了三种受保护的四肽酰胺：Boc-Trp-Met-Asp-X、Boc-Ser-Glu-Ala-X 和 Boc-Ser-Lys-Ala-X，以及两种未受保护的四肽酰胺：H-Trp-Met-Asp-X 和 H-Phe-Met-Arg-X、X=Phe-NH2、Leu-NH2、Phe-NHEt、Val-NH2、Ala-NH2、（对氟）Phe-NH2]，并考察了各种实验条件（pH 值、溶剂和时间）的影响。此外，在热溶解酶的帮助下，通过添加上述各种酰胺，将氧化胰岛素 B 链的 C 端拉长为酰胺。

  DOI：

  10.1248/cpb.36.4345
• 作为产物：
  描述：

  Z(OMe)-Arg(Mts)-OH 在 甲烷磺酸 、 间甲酚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以100%的产率得到H-Arg(Mts)-OH
  参考文献：
  名称：

  通过将间甲酚添加到稀释的甲磺酸中来加速Nα脱保护速率，并将其应用于人胰泌素抑制素29和magainin 1的基于Z（OMe）的固相合成中。

  摘要：

  在固相肽合成中，将间甲酚添加到二氯甲烷中的稀释甲磺酸（MSA）中可加快酸不稳定的α-氨基保护基对甲氧基苄氧基羰基（Z（OMe））的脱保护速度。此外，发现0.1 M MSA，20％间甲酚/ CH2Cl2是一种实用的Nα-脱保护试剂体系，因为Z（OMe）基团的脱保护在室温下30分钟内有选择地发生，而另一个保持完整侧链保护基，例如苄氧基羰基，苄基酯，Sp-甲氧基苄基和NG-均三甲苯基-2-磺酰基。该试剂体系应用于人胰泌素29和magainin 1的基于Z（OMe）的固相合成。

  DOI：

  10.1248/cpb.41.954
• 作为试剂：
  描述：

  Nomega-t-butoxycarbonyl-Nomega-mesitylenesulfonyl-L-arginine 、 盐酸1,4-二恶烷 、 氯化亚砜 、 甲醇 在 乙醚 、 H-Arg(Mts)-OH 、 Boc 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.17h， 生成 H-Arg(Mts)-OMe
  参考文献：
  名称：

  Polypeptide comprising repeated cell-adhesive core sequences

  摘要：

  一种多肽，包括由公式表示的细胞粘附蛋白的重复氨基酸序列：(Arg-Gly-Asp)n或(Tyr-Ile-Gly-Ser-Arg)n，其中n的范围为2至20；或其药物可接受的盐，该多肽作为抗癌转移剂具有价值。

  公开号：

  US05236903A1

文献信息

• Enkephalin analogs containing the dipeptide unit Tyr-Arg (kyotorphin).
  作者：MINORU KUBOTA、OSAMU NAGASE、HIRO AMANO、HIROSHI TAKAGI、HARUAKI YAJIMA

  DOI：10.1248/cpb.28.2580

  日期：——

  Eight Met- and Leu-enkephalin analogs substituted with L- or D-Arg at position 2 were synthesized using NG-mesitylene-2-sulfonylarginine. Among them, H-Tyr-D-Arg-Gly-Phe-Met-OH was found to possess an analgesic effect 2.4 times higher than that of morphine on a molar basis, when injected intracisternally. This compound was also found to produce analgesia when administered intravenously.

  合成了八个在第2位分别用L-或D-精氨酸取代的甲硫脑啡肽和亮脑啡肽类似物，所用原料为NG-间甲苯-2-磺酰精氨酸。在鞘内注射时，发现其中的H-Tyr-D-Arg-Gly-Phe-Met-OH具有比吗啡高2.4倍的镇痛作用（摩尔比）。该化合物经静脉给药时也能产生镇痛作用。
• Studies on peptides. XCV. Alternative synthesis of porcine vasoactive intestinal polypeptide (VIP).
  作者：MASAHARU TAKEYAMA、KANAME KOYAMA、KAZUTOMO INOUE、TAMOTSU KAWANO、ADACHI HIDEKI、TAKAYOSHI TOBE、HARUAKI YAJIMA

  DOI：10.1248/cpb.28.1873

  日期：——

  Two alternative deprotecting procedures were employed for the synthesis of porcine vasoactive intestinal polypeptide (VIP). Besides HF, TFA-thioanisole was found to cleave all the protecting groups employed, Z, Bzl and Mts, suppressing a newly found side reaction, i.e., acid-catalyzed succinimide formation from Asp residues with the free carboxyl group. A small amount of the N-terminal His residue linked to Ser-Asp was found to be released on standing at pH 6.

  猪血管活性肠肽(VIP)的合成采用了两种不同的脱保护程序。除了氢氟酸外，发现TFA-硫代茴香醚能裂解所用的所有保护基团，包括苄酯、甲砷酸和三甲基硅基，并抑制了一种新发现的副反应，即自由羧基的天冬氨酸残基在酸性催化下形成琥珀酰亚胺。在pH 6下静置时，与Ser-Asp相连的N端组氨酸残基有少量被释放。
• Studies on peptides. CL. Syntheses of (D-His2)-analogs of enkephalin and adrenorphin and several (D-Arg2)enkephalin analogs.
  作者：SUSUMU FUNAKOSHI、MINORU KUBOTA、NAOTO KOSUGA、JIAN-PING XU、HARUAKI YAJIMA、WEI LI、SHIGEKI TAMURA、SHUJI KANEKO、MASAMICHI SATOH、HIROSHI TAKAGI

  DOI：10.1248/cpb.35.2561

  日期：——

  [D-His2] Leu-enkephalin and [D-His2] adrenorphin were synthesized. In addition, eight [D-Arg2] enkephalin-related peptides were synthesized. Their inhibitory effects on electrically stimulated myenteric plexus-longitudinal muscle preparations of guinea-pig ileum were examined.

  合成了[D-His2] Leu-脑啡肽和[D-His2] 肾上腺啡肽。此外，还合成了八种[D-Arg2]脑啡肽相关肽。研究了这些肽对电刺激豚鼠回肠肠肌丛纵肌制备物的抑制作用。
• Studies on peptides. XCIV. Synthesis and activity of kyotorphin and its analogs.
  作者：HARUAKI YAJIMA、HIROSHI OGAWA、HIROSHI UEDA、HIROSHI TAKAGI

  DOI：10.1248/cpb.28.1935

  日期：——

  A dipeptide named kyotorphin, H-Tyr-Arg-OH, and its retro isomer were synthesized using NG-mesitylene-2-sulfonylarginine. Two corresponding stereoisomers containing D-Arg were also synthesized. Among these, H-Tyr-D-Arg-OH was found to possess an analgesic effect 6 times higher than that of the corresponding L-isomer.

  使用NG-均三甲苯-2-磺酰精氨酸合成了名为kyotorphin、H-Tyr-Arg-OH 的二肽及其逆向异构体。还合成了两种相应的含有D-Arg 的立体异构体。其中，H-Tyr-D-Arg-OH的镇痛效果比相应的L-异构体高6倍。
• Synthesis and evaluation of peptidomimetics that bind DNA
  作者：Jeffrey A Turk、David B Smithrud

  DOI：10.1016/s0968-0896(02)00646-6

  日期：2003.5

  A peptidomimetic template, consisting of a hydrophobic scaffold, a dansyl fluorophore, and an Arg-His recognition strand, was tested as a simple mimic of zinc finger 2 of the Zif268 protein. Association constants (K-A's) were on the order of 101 M-1 for complexes formed between the mimetic and duplexes d(CGGGAATTCCCG)(2) and d(AAAAAAAAATTTTTTTTT)(2), Modest selectivity was observed for the GC-rich DNA in a 0.5 M NaCl/buffer (0.1 M phosphate, pH 7.0) solution. Differences in KA's along with observed CD profiles suggest that the mimetic associated with the duplexes using different binding modes. The DNA duplexes had weaker interactions with the free Arg-His recognition strand, the dansyl functional group, and a scaffold that contained only glycines as the recognition strand. The scaffold most likely provides for greater van der Waal's interactions, a larger hydrophobic effect upon association, and reduces the freedom of motion of the side chains. This last effect was confirmed by molecular mechanics calculations and by the fact that the mimetic suffered a smaller loss of entropic energy upon association than the free recognition strand. These studies show that the synthetic scaffold is a promising platform in which peptides can be attached to increase their affinity and possibly selectivity for DNA targets. (C) 2003 Elsevier Science Ltd. All rights reserved.