(S)-2-{(R)-2-tert-Butoxycarbonylamino-3-[(R)-2-tert-butoxycarbonylamino-2-((S)-1-methoxycarbonyl-3-methyl-butylcarbamoyl)-ethyldisulfanyl]-propionylamino}-4-methyl-pentanoic acid methyl ester | 352280-85-4

• 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: (S)-2-{(R)-2-tert-Butoxycarbonylamino-3-[(R)-2-tert-butoxycarbonylamino-2-((S)-1-methoxycarbonyl-3-methyl-butylcarbamoyl)-ethyldisulfanyl]-propionylamino}-4-methyl-pentanoic acid methyl ester
• 英文别名: Boc-Cys(1)-Leu-OMe.Boc-Cys(1)-Leu-OMe；methyl (2S)-2-[[(2R)-3-[[(2R)-3-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]disulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-4-methylpentanoate
• CAS: 352280-85-4
• 化学式: C₃₀H₅₄N₄O₁₀S₂
• 分子量: 694.912
• InChiKey: QWQHNUZZJPLTQM-CMOCDZPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  46
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  238
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (S)-2-{(R)-2-tert-Butoxycarbonylamino-3-[(R)-2-tert-butoxycarbonylamino-2-((S)-1-methoxycarbonyl-3-methyl-butylcarbamoyl)-ethyldisulfanyl]-propionylamino}-4-methyl-pentanoic acid methyl ester 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Design, synthesis and membrane ion transport properties of cystine- and serine-based cyclo -4-oxa-heptane-1,7-bisamides

  摘要：

  A new class of cyclobisamides, having the general profile of amino acid (cystine or serine)-ether composites, as potentially efficient ion transporters has been designed and synthesized. In model membranes, the adamantane harboring composites exhibited 57-66% of gramicidin A activity in ion transport. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00979-6
• 作为产物：
  描述：

  (2S)-2-氨基-4-甲基戊酸甲酯 、 N,N'-双(叔丁氧羰基)-L-胱氨酸 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以90%的产率得到(S)-2-{(R)-2-tert-Butoxycarbonylamino-3-[(R)-2-tert-butoxycarbonylamino-2-((S)-1-methoxycarbonyl-3-methyl-butylcarbamoyl)-ethyldisulfanyl]-propionylamino}-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Self-Assembling, Cystine-Derived, Fused Nanotubes Based on Spirane Architecture:  Design, Synthesis, and Crystal Structure of Cystinospiranes

  摘要：

  A novel family of cystine-based spirobicyclic peptides (cystinospiranes) has been synthesized by a single-step procedure involving condensation of pentaerythritol-derived tetrachloride with either the simple L-cystine dimethyl ester or its C,C'-extended bispeptides leading to a variety of 19-membered spirobicyclic peptides or its N,N'-extended bispeptides affording the ring-expanded 25-membered cystinospiranes. The design is flexible with respect to the ring size that can be adjusted depending upon the length of the N,N'-extended cystine bispeptide, and the choice of an amino acid, as illustrated here with the preparation of a large number of cystinospiranes containing a wide variety of amino acids. X-ray crystal structure of the parent spirane (5a) revealed nanotube formation by vertical stacking of relatively flat spirobicyclic molecules through contiguous NH- - -O=C hydrogen bonding. The fused pair of parallel nanotubes is open-ended, hollow, and extends to infinity. Crystallographic parameters are the following: C33H52N4O16S4, space group C2, a = 42.181(3) Angstrom, b = 5.1165(7) Angstrom, c = 11.8687(9) Angstrom, beta = 106.23(1)degrees.

  DOI：

  10.1021/ja0101734

文献信息

• Redox Sensitive Self-Assembling Dipeptide for Sustained Intracellular Drug Delivery
  作者：Sameer Dhawan、Sukanya Ghosh、R. Ravinder、Sachendra S. Bais、Soumen Basak、N. M. Anoop Krishnan、Manish Agarwal、Manidipa Banerjee、V. Haridas

  DOI：10.1021/acs.bioconjchem.9b00532

  日期：2019.9.18

  These peptide vesicles showed a DOX loading capacity of ∼16% (w/w) and redox-triggered controlled release of the packaged drug. The drug-loaded vesicles were able to penetrate into MDA-MB-231 and HeLa cells, and release payload, suggesting their putative use as chemotherapeutic delivery vehicles. These natural peptide-based carriers disassemble inside cells due to the high cytosolic GSH concentration, and

  具有功能性超分子组装的分子的合理设计和合成仍然是具有挑战性的努力。天然结构的自组装纳米结构和微观结构由于具有生物相容性，因此被认为更适合医疗应用。我们首次报告了一种简单的氧化还原反应性二肽，其在水性介质中自组装形成囊泡。基于对照化合物和全原子分子动力学（MD）模拟的实验结果通过色氨酸残基的吲哚环之间的分子间π-π相互作用支持了缔合机理。这些肽小泡显示出〜16％（w / w）的DOX负载量，并通过氧化还原触发了包装药物的控释。载药小泡能够穿透MDA-MB-231和HeLa细胞，并释放有效载荷，表明它们被推定为化学传递工具。这些天然的基于肽的载体由于高的胞质GSH浓度而在细胞内部分解，并且所得的Cys-Trp二肽是可降解的。此处介绍的简约肽设计，加上易于形成可封装化疗药物的囊泡的倾向，为工程靶向缓释药物输送载体打开了无限的潜力。