Vergne, C.; Boury-Esnault, N.; Pérez, T.; Martin, M.-T.; Adeline, M.-T.; Tran Huu Dau, E.; Al-Mourabit, A. (2006). Verpacamides A-D, a novel sequence of Diketopiperazines relating Cyclo(Pro-Pro) to Cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: plausible biogenetic precursors of Pyrrole-2-Aminoimidazole Alkaloids. Organic Letters. 8: 2421-2424.

425868

Vergne, C.; Boury-Esnault, N.; Pérez, T.; Martin, M.-T.; Adeline, M.-T.; Tran Huu Dau, E.; Al-Mourabit, A.

2006

8: 2421-2424.

Publication

Available for editors   [request]

Four C11N5 diketopiperazine metabolites named verpacamides A (6), B (7), C (8), and D (9) consisting of a proline-arginine dipeptide skeleton have been isolated from the marine sponge Axinella vaceleti. Verpacamides A-D are a sequence of metabolites showing the transformation of proline and arginine into the oxidized guanidinyl-cyclo(Pro-Pro) 8 and 9. Compounds 6-9 are structurally and chemically related to C11N5 pyrrole-2-aminoimidazole metabolites also isolated from the Axinellidae and Agelasidae families of sponges and exemplified by dispacamide A (4) and dibromophakellin (10).

Mediterranean

Biochemistry

Porifera

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