RKWRRKWKK-NH2 | 1117993-72-2

• 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: RKWRRKWKK-NH2
• 英文别名: H-Arg-Lys-Trp-Arg-Arg-Lys-Trp-Lys-Lys-NH2；(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]hexanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]hexanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]hexanoyl]amino]hexanamide
• CAS: 1117993-72-2
• 化学式: C₆₄H₁₀₇N₂₅O₉
• 分子量: 1370.72
• InChiKey: KYONAEMIEKIKTP-ZUIOIVFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  98
• 可旋转键数：
  49
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  631
• 氢给体数：
  22
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  Boc-Agr(Tos)-OH 、 N-叔丁氧羰基-N'-(2-氯苄氧羰基)-L-赖氨酸 、 N-叔丁氧羰基-L-色氨酸 在 p-methylbenzhydrylamine resin 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 RKWRRKWKK-NH2
  参考文献：
  名称：

  Penetratin and derivatives acting as antifungal agents

  摘要：

  The synthesis, in vitro evaluation, and conformational study of RQIKTWFQNRRMKWKK-NH2 (penetratin) and related derivatives acting as antifungal agents are reported. Penetratin and some of its derivatives displayed antifungal activity against the human opportunistic pathogenic standardized ATCC strains Candida albicans and Cryptococcus neoformans as well as clinical isolates of C. neoformans. Among the compounds tested, penetratin along with the nonapeptide RKWRRKWKK-NH2 and the tetrapeptide RQKK-NE2 exhibited significant antifungal activities against the Cryptococcus species. A comprehensive conformational analysis on the peptides reported here using three different approaches, molecular mechanics, simulated annealing and molecular dynamics simulations, was carried out. The experimental and theoretical results allow us to identify a topographical template which may provide a guide for the design of new compounds with antifungal characteristics against C. neoformans. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.019

文献信息

• Penetratin and derivatives acting as antifungal agents
  作者：Marcelo F. Masman、Ana M. Rodríguez、Marcela Raimondi、Susana A. Zacchino、Paul G.M. Luiten、Csaba Somlai、Tamas Kortvelyesi、Botond Penke、Ricardo D. Enriz

  DOI：10.1016/j.ejmech.2008.02.019

  日期：2009.1

  The synthesis, in vitro evaluation, and conformational study of RQIKTWFQNRRMKWKK-NH2 (penetratin) and related derivatives acting as antifungal agents are reported. Penetratin and some of its derivatives displayed antifungal activity against the human opportunistic pathogenic standardized ATCC strains Candida albicans and Cryptococcus neoformans as well as clinical isolates of C. neoformans. Among the compounds tested, penetratin along with the nonapeptide RKWRRKWKK-NH2 and the tetrapeptide RQKK-NE2 exhibited significant antifungal activities against the Cryptococcus species. A comprehensive conformational analysis on the peptides reported here using three different approaches, molecular mechanics, simulated annealing and molecular dynamics simulations, was carried out. The experimental and theoretical results allow us to identify a topographical template which may provide a guide for the design of new compounds with antifungal characteristics against C. neoformans. (C) 2008 Elsevier Masson SAS. All rights reserved.