Fmoc-Trp(Boc)-F | 494864-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Trp(Boc)-F
• CAS: 494864-28-7
• 化学式: C₃₁H₂₉FN₂O₅
• 分子量: 528.58
• InChiKey: NQUQOBNCIJBULN-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  86.63
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Trp(Boc)-F 、 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Rapid, Continuous Solution-Phase Peptide Synthesis:  Application to Peptides of Pharmaceutical Interest

  摘要：

  The Fmoc/TAEA and Bsmoc/TAEA methods for the rapid, continuous solution synthesis of peptide segments are shown to be applicable to the gram-scale synthesis of short peptides as well as, for the first time, to the synthesis of a relatively long (22-mer) segment, (hPTH 13-34). In the latter case the crude product was of significantly greater purity than a sample obtained via a solid-phase protocol. The Bsmoc methodology was optimized by a new technique involving filtration of the growing partially deprotected peptide at each coupling-deprotection cycle through a short column of silica gel.

  DOI：

  10.1021/op0202179
• 作为产物：
  描述：

  Fmoc-L-色氨酸(Boc)-OH 在 吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 Fmoc-Trp(Boc)-F
  参考文献：
  名称：

  A multivalent HIV-1 fusion inhibitor based on small helical foldamers

  摘要：

  The peptide sequence AcNH-TEG-Glu-Aib-Trp-AibAib-Trp-AibAib-Ile-Asp OH (1), designed to display the WWI epitope found near the C-terminus of gp41, an envelope glycoprotein decorating the surface of the HIV-1 virus, has been synthesized and proved to have a relevant content of helical conformation because of the presence of five alpha-aminoisobutyric acid (Aib) units. Three copies of it have been connected to a tripodal platform based on 2,4,6-triethylbenzene-1,3,5-trimethylamine. The tripodal template 2 is even more structured than 1 thus suggesting a significant interaction between the three sequences connected to the platform. Preliminary inhibition assays of HIV-mediated cell fusion indicated that while the single peptide 1 is inactive within the concentration range of our assay, when it is conjugated to the tripodal platform, it is moderately active. These promising results suggest that our approach constitute a valid alternative to those reported so far. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.078

文献信息

• A comparison of pseudoproline substitution effects on cyclisation yield in the total syntheses of segetalins B and G
  作者：Michelle S. Y. Wong、Katrina A. Jolliffe

  DOI：10.1002/pep2.24042

  日期：2018.5

  pentapeptides, segetalins B and G, using a traceless pseudoproline‐mediated cyclization reaction is reported. The incorporation of a cysteine‐derived gem‐dimethyl pseudoproline [Cys(ΨMe,MePro)] residue in the linear precursors to induce a cisoid amide bond prior to the head‐to‐tail cyclization resulted in improved cyclization yields in both cases. Cysteine‐derived pseudoproline residues lacking the gem‐dimethyl

  的天然存在的环五肽的全合成，segetalins B和G，使用无痕假脯氨酸-介导的环化反应的报道。在头到尾环化之前，将半胱氨酸衍生的gem-二甲基假脯氨酸[Cys（ΨMe ，Me Pro）]残基掺入以诱导顺式酰胺键，在两种情况下均提高了环化产率。半胱氨酸-缺乏衍生假脯氨酸残基宝石-二甲基取代环[Cys（Ψ H，HPro）]不能有效地诱导酰胺键的顺式构象，并导致环化产率降低，同时环二聚体的形成也随之增加。对含有Cys（ΨMe ，Me Pro）的环肽进行脱保护和脱硫反应，从而以高总收率得到含丙氨酸的天然产物。相反，含有半胱氨酸（Ψ环肽脱保护H，H脯氨酸）残基时，用三氟乙酸处理来除去其它侧链-保护基团，但留下的Cys（Ψ H，H脯氨酸）残基保持不变。