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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.

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Hokkaido University Collection of Scholarly and Academic Papers  

Autor(es)

Casalme, Loida O. -  Yamauchi, Arisa -  Sato, Akinori -  Petitbois, Julie G. -  Nogata, Yasuyuki -  Yoshimura, Erina -  Okino, Tatsufumi -  Umezawa, Taiki -  Matsuda, Fuyuhiko - 

Id.: 70838752

Idioma: inglés  - 

Versión: 1.0

Estado: Final

Palabras clave450 - 

Tipo de recurso: article (author version)  - 

Tipo de Interactividad: Expositivo

Nivel de Interactividad: muy bajo

Audiencia: Estudiante  -  Profesor  -  Autor  - 

Estructura: Atomic

Coste: no

Copyright: sí

Requerimientos técnicos:  Browser: Any - 

Fecha de contribución: 10-ene-2018

Contacto:

Localización:
* Organic & biomolecular chemistry, 15(5): 1140-1150

Otros recursos del mismo autor(es)

  1. New Marine Antifouling Compounds from the Red Alga Laurencia sp. Six new compounds, omaezol, intricatriol, hachijojimallenes A and B, debromoaplysinal, and 11,12-dih...
  2. Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides Biofouling, an undesirable accumulation of organisms on sea-immersed structures such as ship hulls a...
  3. Total synthesis of dolastatin 16 [an abstract of dissertation and a summary of dissertation review]
  4. Total synthesis of dolastatin 16 [an abstract of entire text] この博士論文全文の閲覧方法については、以下のサイトをご参照ください。
  5. Synthetic study on dolastatin 16: concise and scalable synthesis of two unusual amino acid units A convenient and scalable synthesis of two unusual amino acid units found in dolastatin 16, dolaphen...

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