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Studies on Aculeines: Synthetic Strategy to the Fully Protected Protoaculeine B, the N-Terminal Amino Acid of Aculeine B
Organic Letters ( IF 5.2 ) Pub Date : 2018-05-23 00:00:00 , DOI: 10.1021/acs.orglett.8b01331
Hiroki Shiozaki 1 , Masayoshi Miyahara 1 , Kazunori Otsuka 1 , Kei Miyako 2 , Akito Honda 2 , Yuichi Takasaki 1 , Satoshi Takamizawa 1 , Hideyuki Tukada 1 , Yuichi Ishikawa 1 , Ryuichi Sakai 2 , Masato Oikawa 1
Affiliation  

A synthetic strategy for accessing protoaculeine B (1), the N-terminal amino acid of the highly modified peptide toxin aculeine, was developed via the synthesis of the fully protected natural homologue of 1 with a 12-mer poly(propanediamine). The synthesis of mono(propanediamine) analog 2, as well as core amino acid 3, was demonstrated by this strategy. New amino acid 3 induced convulsions in mice; however, compound 2 showed no such activity.

中文翻译:

Ac子碱的研究:完全保护的原ac子碱B,Ac草碱B的N末端氨基酸的合成策略

通过合成具有12-mer聚丙二胺1的完全受保护的天然同源物,开发了一种用于获得原球泡蛋白B(1)(高度修饰的肽毒素球泡蛋白的N末端氨基酸)的合成策略。该策略证明了单(丙二胺)类似物2以及核心氨基酸3的合成。新的氨基酸3诱发小鼠惊厥;但是,化合物2没有这种活性。
更新日期:2018-05-23
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