1208244-27-2Relevant academic research and scientific papers
Synthesis of 7-15N-oroidin and evaluation of utility for biosynthetic studies of pyrrole-imidazole alkaloids by microscale 1H-15N HSQC and FTMS
Wang, Yong-Gang,Morinaka, Brandon I.,Reyes, Jeremy Chris P.,Wolff, Jeremy J.,Romo, Daniel,Molinski, Tadeusz F.
, p. 428 - 434 (2010)
Numerous marine-derived pyrrole-imidazole alkaloids (PIAs), ostensibly derived from the simple precursor oroidin, 1a, have been reported and have garnered intense synthetic interest due to their complex structures and in some cases biological activity; however very little is known regarding their biosynthesis. We describe a concise synthesis of 7-15N-oroidin (Id) from urocanic acid and a direct method for measurement, of 15N incorporation by pulse labeling and analysis by 1D 1H-15N HSQC NMR and FTMS. Using a mock pulse labeling experiment, we estimate the limit of detection (LOD) for incorporation of newly biosynthesized PIA by 1D 1H-15N HSQC to be 0.96 μg equivalent of 15N-oroidin (2.4 nmole) in a background of 1500 μg of unlabeled oroidin. (about 1 part per 1600). 7-15N-Oroidin will find utility in biosynthetic feeding experiments with live sponges to provide direct information to clarify the pathways leading to more complex pyrrole-imidazole alkaloids.
