Z-Val-Aib-Aib-OMe | 132363-02-1

• 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: Z-Val-Aib-Aib-OMe
• CAS: 132363-02-1
• 化学式: C₂₂H₃₃N₃O₆
• 分子量: 435.521
• InChiKey: OFRXOQRLSJTDAX-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  122.83
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Z-Val-Aib-Aib-OMe 在 palladium on activated charcoal sodium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate 、 氢气 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 作用下， 以 二氯甲烷 为溶剂， 反应 62.0h， 生成 Z-Leu-Aib-Pro-Val-Aib-Aib-OH
  参考文献：
  名称：

  Efficient synthesis of alamethicin f-30 using a chloro imidazolidium coupling reagent, CIP

  摘要：

  Alamethicin F-30 has been synthesized in solution using a CIP-additive as a coupling agent and TFA as a final deprotecting reagent. All couplings including those between sterically hindered alpha,alpha-dimethyl amino acid were successfully achieved by a 60 min reaction.

  DOI：

  10.1016/0040-4039(95)02023-i
• 作为产物：
  描述：

  2-amino-2-methylpropionic acid methyl ester 在 palladium on activated charcoal N-羟基-7-氮杂苯并三氮唑 、 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate 、 氢气 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Z-Val-Aib-Aib-OMe
  参考文献：
  名称：

  Efficient synthesis of alamethicin f-30 using a chloro imidazolidium coupling reagent, CIP

  摘要：

  Alamethicin F-30 has been synthesized in solution using a CIP-additive as a coupling agent and TFA as a final deprotecting reagent. All couplings including those between sterically hindered alpha,alpha-dimethyl amino acid were successfully achieved by a 60 min reaction.

  DOI：

  10.1016/0040-4039(95)02023-i

文献信息

• Fungal metabolites. IV. Synthesis of an antibiotic peptide, trichosporin B-V, from Trichoderma polysporum.
  作者：AKira IIDA、Shinya YOSHIMATSU、Masaki SANEKATA、Tetsuro FUJITA

  DOI：10.1248/cpb.38.2997

  日期：——

  The antibiotic icosapeptide trichosporin B-V, which was isolated from Trichoderma polysporum, was synthesized by assembling five peptide fragments via the N,N'-dicyclohexylcarbodiimide method. The synthesized peptide was identical with the natural one.

  从多木霉菌中分离出的抗生素二十碳三肽孢霉菌素BV是通过N，N'-二环己基碳二亚胺法组装五个肽片段而合成的。合成的肽与天然肽相同。
• Fungal Metabolites. XVII. Synthesis and NMR Study of Ion Channel-Forming Peptides, Trichosporin B-VIa and Its Derivative.
  作者：Yasuo NAGAOKA、Akira IIDA、Teturo FUJITA

  DOI：10.1248/cpb.42.1258

  日期：——

  A membrane-modifying peptide antibiotic, trichosporin B-VIa, having catecholamine secretion-inducing activity on bovine adrenal chromaffin cells has been synthesized. Aib14-Trichosporin B-VIa, in which Pro14 was replaced by Aib, has also been synthesized to modify the secondary structure of trichosporin B-VIa. Sequience-specific 1H-NMR assignments of both peptides in methanol were achieved by using two-dimensional NMR techniques.

  我们合成了一种膜修饰肽抗生素--三碳卟啉 B-VIa，它对牛肾上腺绒毛细胞具有儿茶酚胺分泌诱导活性。此外，还合成了 Aib14-Trichosporin B-VIa，其中的 Pro14 被 Aib 取代，从而改变了三叶鞘磷脂 B-VIa 的二级结构。利用二维核磁共振技术实现了这两种肽在甲醇中的序列特异性 1H-NMR 分配。