論文

査読有り 筆頭著者
2014年9月

Total Synthesis and Conformational Analysis of Apratoxin C

JOURNAL OF ORGANIC CHEMISTRY
  • Yuichi Masuda
  • ,
  • Jun Suzuki
  • ,
  • Yuichi Onda
  • ,
  • Yuta Fujino
  • ,
  • Masahito Yoshida
  • ,
  • Takayuki Doi

79
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
DOI
https://doi.org/10.1021/jo501130b
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/25093538
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000341345400021&DestApp=WOS_CPL
ID情報
  • DOI : 10.1021/jo501130b
  • ISSN : 0022-3263
  • PubMed ID : 25093538
  • Web of Science ID : WOS:000341345400021

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