Boc-Trp(Mts)-OH | 92916-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Boc-Trp(Mts)-OH
• 英文别名: (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[1-(2,4,6-trimethylphenyl)sulfonylindol-3-yl]propanoic acid
• CAS: 92916-47-7
• 化学式: C₂₅H₃₀N₂O₆S
• 分子量: 486.589
• InChiKey: FKFFMEHZWLQPKM-FQEVSTJZSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Trp(Mts)-OH 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100%的产率得到L-色氨酸
  参考文献：
  名称：

  肽的研究。CLII。用于肽合成的硬酸脱保护程序。

  摘要：

  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。

  DOI：

  10.1248/cpb.35.3447
• 作为产物：
  描述：

  2,4,6-三甲基苯磺酰氯 、 N-叔丁氧羰基-L-色氨酸苄酯 在 sodium hydroxide 、 十六烷基三甲基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以74%的产率得到Boc-Trp(Mts)-OH
  参考文献：
  名称：

  肽的研究。CXXI。Nin-间苯二甲磺酰基色氨酸，一种肽合成的新衍生物。

  摘要：

  Mts（美克苯磺酰）基团通过Illi的方法引入到色氨酸的N位置。该基团在实际肽合成所需的各种条件下都具有稳定性，例如与稀碱、肼水合物、TFA，甚至4 N HCl-二氧六环或25% HBr-乙酸的处理。HF无法去除该保护基团，但可以通过1 M 三氟甲烷磺酸/TFA或甲烷磺酸顺利断裂。新型色氨酸衍生物Trp（Mts）在实际肽合成中的实用性通过以合成胆囊收缩素七肽为例得到了证明。

  DOI：

  10.1248/cpb.32.2660

文献信息

• Amino Acids and Peptides. LIV. Application of 2-Adamantyl Derivatives as Protecting Groups to the Synthesis of Peptide Fragments Related to Sulfolobus solifataricus Ribnuclease. I.
  作者：Yoshio OKADA、Shima JOSHI、Noriyuki SHINTOMI、Yukihiro KONDO、Yuko TSUDA、Kazuko OHGI、Masachika IRIE

  DOI：10.1248/cpb.47.1089

  日期：——

  The 2-adamantyloxycarbonyl group was employed for the protection of the epsilon-amino group of Lys and the hydroxyl group of Tyr, and the 2-adamantyl ester was employed for the protection of the beta-carboxyl group of Asp in order to construct eight peptide segments as building blocks for the preparation of peptide fragments related to the sequence of Sulfolobus solifataricus Ribonuclease. The usefulness

  2-金刚烷基氧羰基用于保护Lys的ε-氨基和Tyr的羟基，2-金刚烷基酯用于保护Asp的β-羧基，以构建八个肽片段作为构建块，用于制备与Sulfolobus solifataricus核糖核酸酶序列有关的肽片段。证实了在我们实验室开发的上述保护基的有用性。
• Studies on peptides. CXXXIII. Synthesis and biological activity of galanin, a novel porcine intestinal polypeptide.
  作者：HARUAKI YAJIMA、SHIROH FUTAKI、NOBUTAKA FUJII、KENICHI AKAJI、SUSUMU FUNAKOSHI、MITSUYA SAKURAI、SHINICHI KATAKURA、KAZUTOMO INOUE、RYO HOSOTANI、TAKAYOSHI TOBE、TOMIO SEGAWA、ATSUKO INOUE、KAZUHIKO TAKEMOTO、VIKTOR MUTT

  DOI：10.1248/cpb.34.528

  日期：——

  A new porcine gastrointestinal 29-residue peptide, galanin, was synthesized in a satisfactory yield by assembling seven peptide fragments followed by deprotection with 1 M trifluoromethane-sulfonic acid-thioanisole in trifluoroacetic acid. Nin-Mesitylenesulfonyltryptophan was employed to suppress indole alkylation during Na-deprotection. β-Cycloheptylaspartate was employed to suppress base-catalyzed succinimide formation. The synthetic peptide exhibited a powerful contractile activity on rat ileum, but not on guinea pig ileum and caused sustained hyperglycemia in dogs.

  一种新的猪胃肠道29残基肽——加拉宁，通过组合七个肽片段合成，并在三氟醋酸中使用1 M三氟甲烷磺酸-硫代苯醚进行去保护，获得了令人满意的产率。在钠去保护过程中，采用了九甲苯磺酰色氨酸以抑制吲哚烷基化。使用β-环庚基天冬氨酸来抑制碱催化的琥珀酰亚胺形成。合成的肽在大鼠回肠上表现出强有力的收缩活性，但在豚鼠回肠上没有影响，并且在狗身上引起持续性高血糖。
• Studies on peptides. CXXIX. Application of Nin-mesitylenesulfonyltryptophan for the syntheses of neuromedin B and neuromedin C.
  作者：NOBUTAKA FUJII、SHIROH FUTAKI、KENICHI AKAJI、HARUAKI YAJIMA、ATSUKO INOUE、TOMIO SEGAWA

  DOI：10.1248/cpb.33.3731

  日期：——

  Two Trp containing peptides, neuromedins B and C, were synthesized using a new Trp derivative, Nin-mesitylenesulfonyltryptophan, [Trp (Mts)]. The thioanisole-mediated deprotection with trifluoromethanesulfonic acid in trifluoroacetic acid was employed at the final steps of these syntheses to remove the Mts group together with the Nα-protecting group. In this deprotecting step, the use of an additional scavenger, ethanedithiol, was recommended to suppress possible indole modification. When smooth-muscle contractile activity in guinea pig ileum was examined, the relative potencies of neuromedins B and C with respect to synthetic substance P (taken as 1) were 0.46 and 0.37, respectively.

  我们使用一种新的 Trp 衍生物--Nin-甲磺酰色氨酸[Trp (Mts)]合成了两种含 Trp 的肽--神经美多肽 B 和 C。在这些合成的最后步骤中，采用了在三氟乙酸中用三氟甲磺酸进行硫代苯甲醚介导的脱保护作用，以除去 Mts 基团和 Nα 保护基团。在这一脱保护步骤中，建议使用一种额外的清除剂乙二硫醇来抑制可能的吲哚修饰。在检测豚鼠回肠平滑肌的收缩活性时，与合成物质 P（取 1）相比，神经生长因子 B 和 C 的相对效力分别为 0.46 和 0.37。
• β-Methylation of the Phe⁷ and Trp⁹ Melanotropin Side Chain Pharmacophores Affects Ligand−Receptor Interactions and Prolonged Biological Activity
  作者：Carrie Haskell-Luevano、Kate Toth、Lakmal Boteju、Constatin Job、Ana Maria de L. Castrucci、Mac E. Hadley、Victor J. Hruby

  DOI：10.1021/jm970018t

  日期：1997.8.1

  Topographically modified melanotropin side chain pharmacophore residues Phe(7) and Trp(9) in a cyclic peptide template (Ac-Nle(4)-c[Asp-His-Xaa(7)-Arg-Yaa(9)-Lys]-NH2) and Phe(7) in a linear peptide template (Ac-Ser-Tyr-Ser-Nle(4)-Glu-His-Xaa(7)-Arg-Trp-Gly-Lys-Pro-Val-NH2) result in differences in potency and prolonged biological activity in the frog and lizard skin bioassays. These topographic modifications included the four isomers of beta-methylphenylalanine (beta-MePhe)(7) and beta-methyltryptophan (beta-MeTrp)(9) and the two isomers of 1,2,3,4-tetrahydro-beta-carboline (Tea)(9) Modifications in the cyclic template resulted in up to a 1000-fold difference in potency for the beta-MePhe(7) stereoisomeric peptides; up to a 476-fold difference in potency resulted for the beta-MeTrp(9) peptides, and about a 50-fold difference between the Tca(9)-containing peptides. Up to a 40-fold difference in potency resulted for the beta-MePhe(7)? stereoisomeric peptides using the linear template in these assays. The relative potency racing for modifications in the cyclic template of beta-MePhe(7) were 2R,3S > 2S,3S = 2S,3R 2 > 2R,3R in the frog assay and 2S,3R > 2R,3S > 2S,3S > 2R,3R in the lizard assay. The relative potencies for modifications in the cyclic template of beta-MeTrp(9) were 2R,3S > 2R,3R > 2S,3R > 2S,3R in the frog assay and 2S,3S = 2R,3R > 2R,3S > 2S,3R in the lizard assay. The relative potencies for modifications in the cyclic template of Tca(9) were DTca > LTca in both assays, Significant differences in prolonged (residual) activities were also observed for these modified peptides and were dependent upon stereochemistry of the beta-methyl amino acid, peptide template, and bioassay system. Furthermore, comparisons of beta-MeTrp(9) stereoisomeric peptides on the frog, lizard, and human MC1 receptors suggest that structure-activity relationships on both the classical frog and lizard skin bioassays do not necessarily predict corresponding SAR profiles for the human melanocortin receptors, indicating a remarkable species specificity of the MC1 receptor requirements.
• Yajima, Haruaki; Futaki, Shiroh; Otaka, Akira, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 10, p. 4356 - 4361
  作者：Yajima, Haruaki、Futaki, Shiroh、Otaka, Akira、Yamashita, Takeyoshi、Funakoshi, Susumu、et. al.

  DOI：——

  日期：——