Application of Ugi Consecutive Protocol in the Synthesis of a Peptoid Analogue of Verticilide

Application of Ugi Consecutive Protocol in the Synthesis of a Peptoid Analogue of Verticilide

Barreto, Angélica de Fátima S.; Vercillo, Otilie E.; Wessjohann, Ludger A.; Andrade, Carlos Kleber Z.

Abstract:

Peptoids are non-natural molecules being capable to mimic the natural structure of peptides. These mimetics are based on oligo-N-substituted glycine backbones which exhibit proteolytic stability and wide range of biological activities. Verticilide 1 is a cyclic depsipeptide that exhibits insecticidal activity and was isolated from the culture broth of Verticilium sp. FK-1033 (Figure 1). In order to apply the microwave-assisted synthesis of peptoids via Ugi reactions developed by our groups, we decided to perform the synthesis of a peptoid analogue of Verticilide (Figure 1).

Peptoids are non-natural molecules being capable to mimic the natural structure of peptides. These mimetics are based on oligo-N-substituted glycine backbones which exhibit proteolytic stability and wide range of biological activities. Verticilide 1 is a cyclic depsipeptide that exhibits insecticidal activity and was isolated from the culture broth of Verticilium sp. FK-1033 (Figure 1). In order to apply the microwave-assisted synthesis of peptoids via Ugi reactions developed by our groups, we decided to perform the synthesis of a peptoid analogue of Verticilide (Figure 1).

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DOI: 10.5151/chempro-14bmos-R0298-1

Referências bibliográficas

• [1] 1 Monma, S.; Sunazuka, T.; Nagai, K.; Arai, T.; Shiomi, K.; Matsui, R.; Omura, S. Org. Lett. 2006, 24, 5601.
• [2] 2 (a) Vercillo, O. E.; Andrade, C. K. Z.; Wessjohann, L. A. Org. Lett. 2008, 10, 205. (b) Barreto, A .F. S.; Vercillo, O. E.; Birkett, M. A.; Caulfied, J. C.; Wessjohann, L. A.; Andrade, C. K. Z. Org. Biom. Chem. 2011 accepted.

Como citar:

Barreto, Angélica de Fátima S.; Vercillo, Otilie E.; Wessjohann, Ludger A.; Andrade, Carlos Kleber Z.; "Application of Ugi Consecutive Protocol in the Synthesis of a Peptoid Analogue of Verticilide", p-298-298. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0298-1