RQIRRWWQWRR-NH2 | 1207982-28-2

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: RQIRRWWQWRR-NH2
• 英文别名: H-Arg-Gln-Ile-Arg-Arg-Trp-Trp-Gln-Trp-Arg-Arg-NH2；(2S)-N-[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-2-[[(2S)-2-amino-5-carbamimidamidopentanoyl]amino]pentanediamide
• CAS: 1207982-28-2
• 化学式: C₇₉H₁₂₀N₃₂O₁₃
• 分子量: 1726.03
• InChiKey: MGBLZQPJJSUMOE-HRQCMSGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  124
• 可旋转键数：
  60
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  803
• 氢给体数：
  32
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  BOC-L-异亮氨酸 、 Boc-L-谷氨酰胺 、 N-叔丁氧羰基-N'-甲苯磺酰基-L-精氨酸 、 N-叔丁氧羰基-L-色氨酸 在 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 3.5h， 生成 RQIRRWWQWRR-NH2
  参考文献：
  名称：

  New small-size peptides possessing antifungal activity

  摘要：

  The synthesis, in vitro evaluation, and conformational study of a new series of small-size peptides acting as antifungal agents are reported. In a first step of our study we performed a conformational analysis using Molecular Mechanics calculations. The electronic study was carried out using Molecular electrostatic potentials (MEPs) obtained from RHF/6-31G calculations. On the basis of the theoretical predictions three small-size peptides, RQWKKWWQWRR-NH2, RQIRRWWQWRR-NH2, and RQIRRWWQW-NH2 were synthesized and tested. These peptides displayed a significant antifungal activity against human pathogenic strains including Candida albicans and Cryptococcus neoformans. Our experimental and theoretical results allow the identification of a topographical template which can serve as a guide for the design of new compounds with antifungal properties for potential therapeutic applications against these pathogenic fungi. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.009

文献信息

• New small-size peptides possessing antifungal activity
  作者：Francisco M. Garibotto、Adriana D. Garro、Marcelo F. Masman、Ana M. Rodríguez、Paul G.M. Luiten、Marcela Raimondi、Susana A. Zacchino、Csaba Somlai、Botond Penke、Ricardo D. Enriz

  DOI：10.1016/j.bmc.2009.11.009

  日期：2010.1

  The synthesis, in vitro evaluation, and conformational study of a new series of small-size peptides acting as antifungal agents are reported. In a first step of our study we performed a conformational analysis using Molecular Mechanics calculations. The electronic study was carried out using Molecular electrostatic potentials (MEPs) obtained from RHF/6-31G calculations. On the basis of the theoretical predictions three small-size peptides, RQWKKWWQWRR-NH2, RQIRRWWQWRR-NH2, and RQIRRWWQW-NH2 were synthesized and tested. These peptides displayed a significant antifungal activity against human pathogenic strains including Candida albicans and Cryptococcus neoformans. Our experimental and theoretical results allow the identification of a topographical template which can serve as a guide for the design of new compounds with antifungal properties for potential therapeutic applications against these pathogenic fungi. (C) 2009 Elsevier Ltd. All rights reserved.