3-[(3S,9S,12S,15S,21S,36S,39S)-34-(2-amino-2-oxoethyl)-36-(2-carboxyethyl)-25-[5-[(3',6'-dihydroxy-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-yl)carbamothioylamino]pentanoyl]-12-[(1R)-1-hydroxyethyl]-9-methyl-2,8,11,14,20,23,35,38-octaoxo-1,7,10,13,19,22,25,34,37-nonazatetracyclo[37.3.0.03,7.015,19]dotetracont-31-en-21-yl]propanoic acid | 1209413-52-4

• 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: 3-[(3S,9S,12S,15S,21S,36S,39S)-34-(2-amino-2-oxoethyl)-36-(2-carboxyethyl)-25-[5-[(3',6'-dihydroxy-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-yl)carbamothioylamino]pentanoyl]-12-[(1R)-1-hydroxyethyl]-9-methyl-2,8,11,14,20,23,35,38-octaoxo-1,7,10,13,19,22,25,34,37-nonazatetracyclo[37.3.0.03,7.015,19]dotetracont-31-en-21-yl]propanoic acid
• CAS: 1209413-52-4
• 化学式: C₇₀H₈₈N₁₂O₂₀S
• 分子量: 1449.6
• InChiKey: RUCVIZXGQWVZRR-QNCWIABHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  103.0
• 可旋转键数：
  15.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  455.92
• 氢给体数：
  12.0
• 氢受体数：
  19.0

反应信息

• 作为产物：
  描述：

  fluorescein isothiocyanate 、 Barbatellarines B 在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 生成 3-[(3S,9S,12S,15S,21S,36S,39S)-34-(2-amino-2-oxoethyl)-36-(2-carboxyethyl)-25-[5-[(3',6'-dihydroxy-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-yl)carbamothioylamino]pentanoyl]-12-[(1R)-1-hydroxyethyl]-9-methyl-2,8,11,14,20,23,35,38-octaoxo-1,7,10,13,19,22,25,34,37-nonazatetracyclo[37.3.0.03,7.015,19]dotetracont-31-en-21-yl]propanoic acid
  参考文献：
  名称：

  Application of ring-closing metathesis macrocyclization to the development of Tsg101-binding antagonists

  摘要：

  HIV-1 viral budding involves binding of the viral Gag(p6) protein to the ubiquitin E2 variant domain of the human tumor susceptibility gene 101 protein (Tsg101). Recognition of p6 by Tsg101 is mediated in part by a proline-rich motif that contains the sequence 'Pro-Thr-Ala-Pro' ('PTAP'). Using the p6-derived 9-mer sequence 'PEPTAPPEE', we had previously improved peptide binding affinity by employing N-alkylglycine ('peptoid') residues. The current study applies ring-closing metathesis macrocyclization strategies to Tsg101-binding peptide-peptoid hybrids as an approach to stabilize binding conformations and to observe the effects of such macrocyclization on Tsg101-binding affinity and bioavailability. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.10.105