Effective Synthesis and Antifouling Activity of Dolastatin 16 Derivatives
2022
Loida O. Casalme | Keisuke Katayama | Yoshiki Hayakawa | Kensuke Nakamura | Arisa Yamauchi | Yasuyuki Nogata | Erina Yoshimura | Fuyuhiko Matsuda | Taiki Umezawa
Some derivatives of dolastatin 16, a depsipeptide natural product first obtained from the sea hare <i>Dolabella auricularia</i>, were synthesized through second-generation synthesis of two unusual amino acids, dolaphenvaline and dolamethylleuine. The second-generation synthesis enabled derivatizations such as functionalization of the aromatic ring in dolaphenvaline. The derivatives of fragments and whole structures were evaluated for antifouling activity against the cypris larvae of <i>Amphibalanus amphitrite.</i> Small fragments inhibited the settlement of the cypris larvae at potent to moderate concentrations (EC<sub>50</sub> = 0.60-4.62 μg/mL), although dolastatin 16 with a substituent on the aromatic ring (<b>24</b>) was much less potent than dolastatin 16.
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