2014年9月
Total Synthesis and Conformational Analysis of Apratoxin C
JOURNAL OF ORGANIC CHEMISTRY
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- 巻
- 79
- 号
- 17
- 開始ページ
- 8000
- 終了ページ
- 8009
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/jo501130b
- 出版者・発行元
- AMER CHEMICAL SOC
Total synthesis of apratoxin C, a cyanobacterial cyclodepsipeptide with highly potent cytotoxicity against some cancer cell lines, was achieved using the apratoxin A synthetic strategy developed by us. To elucidate the relationship between conformation and activity, the tertiary structure of apratoxin C was analyzed by NMR spectroscopy. We obtained 37 ROEs and five (3)J(H,H) values, which were translated into distance and dihedral angle constraints, respectively. Molecular modeling was performed with a restrained conformational search by a distance geometry method. The lowest energy structure indicated that the methyl group at C37 and the isopropyl group at C39 play critical roles in maintaining the conformation, whereas the methyl group at C34 does not. Moreover, we confirmed that apratoxin A and C possess similar conformations, providing a likely explanation for their nearly equivalent cytotoxicities.
- リンク情報
- ID情報
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- DOI : 10.1021/jo501130b
- ISSN : 0022-3263
- PubMed ID : 25093538
- Web of Science ID : WOS:000341345400021