title: Concise and efficient synthesis of 3'-O-tetraphosphates of 2'-deoxyadenosine and 2'-deoxycytidine.
abstract: We describe concise and efficient synthesis of biologically very important 3'-O-tetraphosphates namely 2'-deoxyadenosine-3'-O-tetraphosphate (2'-d-3'-A4P) and 2'-deoxycytidine-3'-O-tetra-phosphate (2'-d-3'-C4P). N(6)-benzoyl-5'-O-levulinoyl-2'-deoxyadenosine was converted into N(6)-benzoyl-5'-O-levulinoyl-2'-deoxyadenosine-3'-O-tetraphosphate in 87% yield using a one-pot synthetic methodology. One-step concurrent deprotection of N(6)-benzoyl and 5'-O-levulinoyl groups using concentrated aqueous ammonia resulted 2'-d-3'-A4P in 74% yield. The same synthetic strategy was successfully employed to convert N(4)-benzoyl-5'-O-levulinoyl-2'-deoxycytidine into 2'-d-3'-C4P in 68% yield.
authors.affiliation: a Life Sciences Solutions Group, Thermo Fisher Scientific , Austin , Texas , USA.
authors.forename: Anilkumar R
authors.initials: AR
authors.lastname: Kore
authors.forename: Bo
authors.initials: B
authors.lastname: Yang
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Srinivasan
authors.forename: Annamalai
authors.initials: A
authors.lastname: Senthilvelan
mesh_terms: D003838:Deoxyadenine Nucleotides / Q000138:chemical synthesis*; D003845:Deoxycytosine Nucleotides / Q000138:chemical synthesis*
chemical_list: C114742:2'-deoxyadenosine 3'-tetraphosphate; D003838:Deoxyadenine Nucleotides; D003845:Deoxycytosine Nucleotides
keywords: Nucleoside tetraphosphate; concise synthesis; deprotection; one-pot methodology; phosphorylation