Synthesis of the marine natural product nalpha-(4-bromopyrrolyl-2-carbonyl)-L-homoarginine, a putative biogenetic precursor of the pyrrole-imidazole alkaloids.
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.
Lindel
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T
Pharmazeutisch-chemisches Institut der Universität, INF 364, D-69120 Heidelberg, Germany. thomas.lindel@urz.uniheidelberg.de
Hochgürtel
M
M
Assmann
M
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Köck
M
M
D000470:Alkaloids / Q000378:metabolism; D000818:Animals; D006709:Homoarginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006900:Hydroxylation; D007093:Imidazoles / Q000378:metabolism; D008239:Lysine / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D011161:Porifera / Q000737:chemistry*; D011758:Pyrroles / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment
D000470:Alkaloids; D007093:Imidazoles; C420273:Nalpha-(4-bromopyrrolyl-2-carbonyl)homoarginine; D011758:Pyrroles; D006709:Homoarginine; D008239:Lysine