title: A direct synthesis of pyrrolocytosine from 5-iodocytosine.
abstract: We have employed a tandem Sonogashira/annulation reaction between 5-iodocytosine derivatives and terminal alkynes to yield the fluorescent bicyclic nucleobase pyrrolcytosine. Pyrrolocytosine bearing substituents only on the pyrrole ring are conveniently synthesized from 5-iodocytosine. Water soluble pyrrolocytosines are being investigated as reporter groups in SNP analysis.
authors.affiliation: Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada.
authors.forename: R H E
authors.initials: RH
authors.lastname: Hudson
authors.forename: A K
authors.initials: AK
authors.lastname: Dambenieks
authors.forename: R D
authors.initials: RD
authors.lastname: Viirre
mesh_terms: D002626:Chemistry, Pharmaceutical / Q000379:methods; D003596:Cytosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D015341:Nucleic Acid Probes / Q000737:chemistry / Q000494:pharmacology; D020641:Polymorphism, Single Nucleotide; D017422:Sequence Analysis, DNA / Q000379:methods; D014867:Water / Q000737:chemistry
chemical_list: D015341:Nucleic Acid Probes; C486438:pyrrolo-deoxycytosine; D014867:Water; C008143:5-iodocytosine; D003596:Cytosine