theonellapeptolide Id | 105091-14-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: theonellapeptolide Id
• 英文别名: Theonellamine B；(2R)-2-[[(2S)-2-[(2-methoxyacetyl)amino]-3-methylbutanoyl]-methylamino]-4-methyl-N-[(3R,6R,13S,16S,19R,26S,29R,36S,37R)-3,19,26-tris[(2S)-butan-2-yl]-4,13,14,17,27,37-hexamethyl-6,29-bis(2-methylpropyl)-2,5,8,12,15,18,21,25,28,31,35-undecaoxo-16-propan-2-yl-1-oxa-4,7,11,14,17,20,24,27,30,34-decazacycloheptatriacont-36-yl]pentanamide
• CAS: 105091-14-3
• 化学式: C₇₀H₁₂₅N₁₃O₁₆
• 分子量: 1404.84
• InChiKey: VQXFIQOSHUFNMV-GLVGHDDMSA-N

物化性质

• 沸点：
  1475.2±65.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  99
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  370
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  theonellapeptolide Id 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  New Cyclic Peptides from the Indonesian Sponge Theonella swinhoei

  摘要：

  Three new cyclic peptides, barangamides B, C, and D and a new depsipeptide, theonellapeptolide IIe as well as known theonellapeptolides Ia, Id, Ie, IId have been isolated from the sponge Theonella swinhoei collected in Baranglompo Island, Indonesia. The structures of barangamides were elucidated by interpretation of NMR data and application of Marfey's method. The structure of theonellapeptolide IIe, a mixture of several conformers showing complex NMR spectra, was determined by MS analysis of a ring-opened product and by chemical reaction. Some of the theonellapeptolides showed mild immunosuppressive activity, while barangamide A was inactive. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00762-6
• 作为产物：
  描述：

  MeOAc-Val-D-N(Me)Leu-Thr(1)-bAla-D-Leu-N(Me)Ile-bAla-D-aIle-N(Me)Val-N(Me)Ala-bAla-D-Leu-OH.Me-D-aIle-(1) 在 2,4,6-三甲基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以11.8 mg的产率得到theonellapeptolide Id
  参考文献：
  名称：

  Theonellapeptolide id的全合成

  摘要：

  Theonellapeptolide Id是一种三十七肽，含有37个成员的内酯，最初是从海洋海绵Theonella swinhoei中分离出来的。除了中度的细胞毒性外，还报道了这种天然环二肽的免疫抑制活性。但是，迄今尚无用于证明其独特生物活性的合成材料。在这项研究中，通过固相肽合成法完成了对茶黄素内酯Id的首次全合成，并且与环孢菌素A相比，已经证实了其生物学活性。

  DOI：

  10.1021/acs.orglett.7b00249

文献信息

• Ionophoretic activities of oligopeptide lactones and resin-glycosides in human erythrocytes.
  作者：Isao KITAGAWA、Kazuyoshi OHASHI、Hiroyuki KAWANISHI、Hirotaka SHIBUYA、Kiyoko SHINKAI、Hitoshi AKEDO

  DOI：10.1248/cpb.37.1679

  日期：——

  Oligopeptide lactones (theonellapeptolides) isolated from the Okinawan marine sponge Theonella swinhoei and resin-glycosides (merremosides) from the tuber of an Indonesian medicinal plant Merremia mammosa were examined regarding their activities in transporting Na+, K+, and Ca++ ions into human erythrocytes. Each of these lactones, which had been shown, using a supported liquid membrane, to have an ionophoretic effect on the alkali metal ions, transported the ions to a different extent. The ion transporting activities of these compounds were completely lost when the macrocyclic lactone structures were cleaved by sodium methylate. Resin-glycosides with an additional branched glycosyl residue showed much greater ion transporting activities than those without it.

  我们研究了从冲绳海洋海绵 Theonella swinhoei 和印度尼西亚药用植物 Merremia mammosa 的块茎中分离出的低聚肽内酯（Theonellapeptolides）和树脂糖苷（merremosides）在将 Na+、K+ 和 Ca++ 离子转运到人体红细胞方面的活性。使用支撑液膜证明，每种内酯对碱金属离子都有离子导引作用，但其离子导引程度各不相同。当大环内酯结构被甲基酸钠裂解时，这些化合物的离子传输活性完全丧失。具有额外支化糖基残基的树脂苷的离子转运活性要比没有支化糖基残基的树脂苷高得多。
• New Cyclic Peptides from the Indonesian Sponge Theonella swinhoei
  作者：Michael C. Roy、Ikuko I. Ohtani、Toshio Ichiba、Junichi Tanaka、Rachmaniar Satari、Tatsuo Higa

  DOI：10.1016/s0040-4020(00)00762-6

  日期：2000.11

  Three new cyclic peptides, barangamides B, C, and D and a new depsipeptide, theonellapeptolide IIe as well as known theonellapeptolides Ia, Id, Ie, IId have been isolated from the sponge Theonella swinhoei collected in Baranglompo Island, Indonesia. The structures of barangamides were elucidated by interpretation of NMR data and application of Marfey's method. The structure of theonellapeptolide IIe, a mixture of several conformers showing complex NMR spectra, was determined by MS analysis of a ring-opened product and by chemical reaction. Some of the theonellapeptolides showed mild immunosuppressive activity, while barangamide A was inactive. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Total Synthesis of Theonellapeptolide Id
  作者：Takefumi Kuranaga、Ayumu Enomoto、Hui Tan、Kazuto Fujita、Toshiyuki Wakimoto

  DOI：10.1021/acs.orglett.7b00249

  日期：2017.3.17

  isolated from the marine sponge Theonella swinhoei. In addition to moderate cytotoxicity, immunosuppressive activity had been reported for this natural cyclodepsipeptide. However, the synthetic material to verify its unique biological activity has not been available thus far. In this study, the first total synthesis of theonellapeptolide Id has been performed by solid phase peptide synthesis, and the biological

  Theonellapeptolide Id是一种三十七肽，含有37个成员的内酯，最初是从海洋海绵Theonella swinhoei中分离出来的。除了中度的细胞毒性外，还报道了这种天然环二肽的免疫抑制活性。但是，迄今尚无用于证明其独特生物活性的合成材料。在这项研究中，通过固相肽合成法完成了对茶黄素内酯Id的首次全合成，并且与环孢菌素A相比，已经证实了其生物学活性。