stylissamide G | 1572176-33-0

• 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: stylissamide G
• 英文别名: styllisamide G；cyclo[Ile-Pro-Phe-Pro-Phe-Pro-Leu]；(3S,6S,12S,15S,21S,24S,27S)-3,12-dibenzyl-21-[(2S)-butan-2-yl]-24-(2-methylpropyl)-1,4,10,13,19,22,25-heptazatetracyclo[25.3.0.06,10.015,19]triacontane-2,5,11,14,20,23,26-heptone
• CAS: 1572176-33-0
• 化学式: C₄₅H₆₁N₇O₇
• 分子量: 812.022
• InChiKey: CNDYTKIEBKODPQ-YBHWYGJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  59
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  stylissamide G 在 盐酸 作用下， 以 水 为溶剂， 反应 15.0h， 生成 L-亮氨酸 、 L-异亮氨酸 、 L-苯丙氨酸 、 L-脯氨酸
  参考文献：
  名称：

  Structures and Solution Conformational Dynamics of Stylissamides G and H from the Bahamian Sponge Stylissa caribica

  摘要：

  Two new peptides, stylissamides G and H, were isolated from extracts of a sample of Stylissa caribica collected in deep waters of the Caribbean Sea. A single sample of S. caribica among a collection of 10 samples that were examined by LC-MS appeared to be a different chemotype from the others in that it lacked the familiar pyrrole-2-aminoimidazole alkaloids, stevensine and oroidin, and contained peptides of the stylissamide class. The structures of the title compounds were solved by integrated analysis of the MS and NMR spectra and chemical degradation. The solution conformation of stylissamide G was briefly examined by electronic circular dichroism and temperature-dependent (1)H NMR chemical shifts of amide NH signals, which supported a conformationally rigid macrocycle.

  DOI：

  10.1021/np400891s
• 作为产物：
  描述：

  在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 stylissamide G
  参考文献：
  名称：

  渗透的非经典尺寸依赖性为药物分子的被动吸附定义边界。

  摘要：

  大环肽被认为足够大以抑制“非药物”靶标，但由于分子大小对被动膜通透性的作用尚不为人所知，因此在该空间中被动渗透细胞的设计仍然是一个挑战。使用拆分池组合合成，我们构建了一个环状的，每N个甲基化的肽库，该库涵盖了广泛的计算脂蛋白性（0 < A log P<8）和分子量（〜800 Da

  DOI：

  10.1021/acs.jmedchem.6b01483

文献信息

• Structures and Solution Conformational Dynamics of Stylissamides G and H from the Bahamian Sponge <i>Stylissa caribica</i>
  作者：Xiao Wang、Brandon I. Morinaka、Tadeusz F. Molinski

  DOI：10.1021/np400891s

  日期：2014.3.28

  Two new peptides, stylissamides G and H, were isolated from extracts of a sample of Stylissa caribica collected in deep waters of the Caribbean Sea. A single sample of S. caribica among a collection of 10 samples that were examined by LC-MS appeared to be a different chemotype from the others in that it lacked the familiar pyrrole-2-aminoimidazole alkaloids, stevensine and oroidin, and contained peptides of the stylissamide class. The structures of the title compounds were solved by integrated analysis of the MS and NMR spectra and chemical degradation. The solution conformation of stylissamide G was briefly examined by electronic circular dichroism and temperature-dependent (1)H NMR chemical shifts of amide NH signals, which supported a conformationally rigid macrocycle.
• Nonclassical Size Dependence of Permeation Defines Bounds for Passive Adsorption of Large Drug Molecules
  作者：Cameron R. Pye、William M. Hewitt、Joshua Schwochert、Terra D. Haddad、Chad E. Townsend、Lyns Etienne、Yongtong Lao、Chris Limberakis、Akihiro Furukawa、Alan M. Mathiowetz、David A. Price、Spiros Liras、R. Scott Lokey

  DOI：10.1021/acs.jmedchem.6b01483

  日期：2017.3.9

  Macrocyclic peptides are considered large enough to inhibit “undruggable” targets, but the design of passively cell-permeable molecules in this space remains a challenge due to the poorly understood role of molecular size on passive membrane permeability. Using split-pool combinatorial synthesis, we constructed a library of cyclic, per-N-methlyated peptides spanning a wide range of calculated lipohilicities

  大环肽被认为足够大以抑制“非药物”靶标，但由于分子大小对被动膜通透性的作用尚不为人所知，因此在该空间中被动渗透细胞的设计仍然是一个挑战。使用拆分池组合合成，我们构建了一个环状的，每N个甲基化的肽库，该库涵盖了广泛的计算脂蛋白性（0 < A log P<8）和分子量（〜800 Da