RESUMEN

Lysine is proposed as an alternative biosynthetic precursor of the pyrrole-imidazole alkaloids frequently found in marine sponges. As a putative key intermediate, the natural product Nalpha-(4-bromopyrrolyl-2-carbonyl)-L-homoarginine (1) from the sponge Agelas wiedenmayeri was synthesized in the solid phase starting from Fmoc/Pmc-protected L-homoarginine and in solution starting from readily available L-lysine methyl ester.

Asunto(s)

Homoarginina/análogos & derivados , Poríferos/química , Alcaloides/metabolismo , Animales , Homoarginina/síntesis química , Homoarginina/química , Hidroxilación , Imidazoles/metabolismo , Lisina/química , Lisina/metabolismo , Espectroscopía de Resonancia Magnética , Pirroles/metabolismo , Espectrometría de Masa Bombardeada por Átomos Veloces