Isolation and synthesis of 4-bromopyrrole-2-carboxyarginine and 4-bromopyrrole-2-carboxy-N(epsilon)-lysine from the marine sponge Stylissa caribica.
Two new bromopyrrole alkaloids were isolated from the Caribbean sponge Stylissa caribica. The new natural products, 4-bromopyrrole-2-carboxyarginine (1) and 4-bromopyrrole-2-carboxy-N(epsilon)-lysine (2), are derivatives of amino acids linked with a 4-bromopyrrole-2-carboxylic acid. The structures were elucidated on the basis of NMR and MS/MS data and their absolute configurations assigned via synthesis.
Grube
Achim
A
Alfred-Wegener-Institut für Polar- und Meeresforschung in der Helmholtz-Gemeinschaft, Am Handelshafen 12, D-27570 Bremerhaven, Germany.
Lichte
Ellen
E
Köck
Matthias
M
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D000818:Animals; D001120:Arginine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000302:isolation & purification*; D017691:Caribbean Region; D008239:Lysine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D011758:Pyrroles
C508642:4-bromopyrrole-2-carboxy-N(epsilon)lysine; C508641:4-bromopyrrole-2-carboxyarginine; D000470:Alkaloids; D011758:Pyrroles; D001120:Arginine; D008239:Lysine