title: One-step protecting-group-free synthesis of azepinomycin in water.
abstract: We report an efficient, atom economical general acid-base catalyzed one-step multi-gram synthesis of azepinomycin from commercially available compounds in water. We propose that the described pH-dependent Amadori rearrangement, which couples an amino-imidazole and simple sugar, is of importance as a potential step toward predisposed purine nucleotide synthesis at the origins of life.
authors: University College London, 20 Gordon Street, London WC1H 0AJ, UK. matthew.powner@ucl.ac.uk.
authors: Adam J
authors: AJ
authors: Coggins
authors: Derek A
authors: DA
authors: Tocher
authors: Matthew W
authors: MW
authors: Powner
mesh_terms: D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D014867:Water / Q000737:chemistry*
chemical_list: D001381:Azepines; D014867:Water; C054358:azepinomycin