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Total synthesis and biological activity of dolastatin 16

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タイトル: Total synthesis and biological activity of dolastatin 16
著者: Casalme, Loida O. 著作を一覧する
Yamauchi, Arisa 著作を一覧する
Sato, Akinori 著作を一覧する
Petitbois, Julie G. 著作を一覧する
Nogata, Yasuyuki 著作を一覧する
Yoshimura, Erina 著作を一覧する
Okino, Tatsufumi 著作を一覧する
Umezawa, Taiki 著作を一覧する
Matsuda, Fuyuhiko 著作を一覧する
発行日: 2017年 1月 4日
出版者: Royal Society of Chemistry
誌名: Organic & biomolecular chemistry
巻: 15
号: 5
開始ページ: 1140
終了ページ: 1150
出版社 DOI: 10.1039/c6ob02657e
抄録: The total synthesis of dolastatin 16, a macrocyclic depsipeptide first isolated from the sea hare Dolabella auricularia as a potential antineoplastic metabolite by Pettit et al., was achieved in a convergent manner. Dolastatin 16 was reported by Tan to exhibit strong antifouling activity, and thus shows promise for inhibiting the attachment of marine benthic organisms such as Amphibalanus amphitrite to ships and submerged artificial structures. Therefore, dolastatin 16 is a potential compound for a new, environmentally friendly antifouling material to replace banned tributyltin-based antifouling paints. The synthesis of dolastatin 16 involved the use of prolinol to prevent formation of a diketopiperazine composed of L-proline and N-methyl-D-valine during peptide coupling. This strategy for the elongation of peptide chains allowed the efficient and scalable synthesis of one segment, which was subsequently coupled with a second segment and cyclized to form the macrocyclic framework of dolastatin 16. The synthetic dolastatin 16 exhibited potent antifouling activity similar to that of natural dolastatin 16 toward cypris larvae of Amphibalanus amphitrite.
資料タイプ: article (author version)
出現コレクション:雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

提供者: 梅澤 大樹


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