title: A simple, convenient method to synthesize cobalamins: synthesis of homocysteinylcobalamin, N-acetylcysteinylcobalamin, 2-N-acetylamino-2-carbomethoxyethanethiolatocobalamin, sulfitocobalamin and nitrocobalamin.
abstract: Glutathionylcobalamin, nitrocobalamin and sulfitocobalamin are important cobalamin metabolites isolable from human tissues. Herein we demonstrate that a procedure used to synthesize and isolate gamma-glutamylcysteinylcobalamin and glutathionylcobalamin in aqueous solution in high yield and purity can be used to synthesize other novel, biologically relevant thiolatocobalamins, including d,l-homocysteinylcobalamin, N-acetyl-l-cysteinylcobalamin (Na(+) salt) and 2-N-acetylamino-2-carbomethoxy-l-ethanethiolatocobalamin, as well as other non-alkylcobalamins, such as sulfitocobalamin (Na(+) salt) and nitrocobalamin. This uncomplicated, general procedure will assist researchers in identifying unknown cobalamin metabolites isolated from biological samples, and researchers interested in studying the uptake and intracellular cobalamin processing mechanisms utilizing non-alkylcobalamin derivatives that are not yet commercially available. The X-ray structure and XAS spectrum of N-acetyl-l-cysteinylcobalamin are also presented.
authors.affiliation: School of Biomedical Sciences, Kent State University, Kent, OH 44240, USA.
authors.forename: Edward
authors.initials: E
authors.lastname: Suarez-Moreira
authors.forename: Luciana
authors.initials: L
authors.lastname: Hannibal
authors.forename: Clyde A
authors.initials: CA
authors.lastname: Smith
authors.forename: Roberto A
authors.initials: RA
authors.lastname: Chavez
authors.forename: Donald W
authors.initials: DW
authors.lastname: Jacobsen
authors.forename: Nicola E
authors.initials: NE
authors.lastname: Brasch
mesh_terms: D018360:Crystallography, X-Ray; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006710:Homocysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D014805:Vitamin B 12 / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C516436:2-N-acetylamino-2-carbomethoxyethanethiolatocobalamin; C516435:N-acetylcysteinylcobalamin; C516434:homocysteinylcobalamin; D006710:Homocysteine; C016763:sulfitocobalamin; C092105:nitritocobalamin; D003545:Cysteine; D014805:Vitamin B 12