title: Synthesis of oligodeoxynucleoside methylphosphonates utilizing the tert-butylphenoxyacetyl group for exocyclic amine protection.
abstract: Oligodeoxynucleoside methylphosphonates were synthesized using methylphosphonamidite monomers incorporating the base labile tert-butylphenoxyacetyl (t-BPA) protecting group on the exocyclic amines of dA, dC, and dG. Synthesis of the oligodeoxynucleoside methylphosphonates required only a small change in oxidation solution from standard DNA synthesis. The increased lability of the t-BPA group over the standard benzoyl and isobutyryl protection permitted the use of milder basic deprotection conditions. Deprotection of the nucleoside bases and release from support was best accomplished by a short treatment with ammonia saturated methanol. This procedure resulted in minimal backgone degradation with no base modifications. Analysis of the resultant oligodeoxynucleoside methylphosphonates by reverse phase HPLC and MALDI-TOF mass spectroscopy are described.
authors.affiliation: Nucleic Acid Chemistry Group, Millipore Corp., Bedford, MA 01730.
authors.forename: N D
authors.initials: ND
authors.lastname: Sinha
authors.forename: D P
authors.initials: DP
authors.lastname: Michaud
authors.forename: S K
authors.initials: SK
authors.lastname: Roy
authors.forename: R A
authors.initials: RA
authors.lastname: Casale
mesh_terms: D000215:Acylation; D000641:Ammonia; D002851:Chromatography, High Pressure Liquid; D003839:Deoxyadenosines / Q000737:chemistry; D003841:Deoxycytidine / Q000737:chemistry; D003849:Deoxyguanosine / Q000737:chemistry; D013058:Mass Spectrometry; D000432:Methanol; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000302:isolation & purification; D010084:Oxidation-Reduction; D012996:Solutions
chemical_list: D003839:Deoxyadenosines; D009838:Oligodeoxyribonucleotides; D012996:Solutions; C021992:dideoxyribonucleoside methylphosphonates; D003841:Deoxycytidine; D000641:Ammonia; D003849:Deoxyguanosine; D000432:Methanol