Synthesis and separation of diastereomers of ribonucleoside 5{prime}-({alpha}-P-borano)triphosphates
Journal Article
·
· Journal of Organic Chemistry
- Duke Univ., Durham, NC (United States)
Nucleoside boranophosphates, in which one of the phosphate oxygens is replaced by a borane group, are isoionic and isoelectronic analogues of naturally occurring nucleotides. Boranophosphates also are biochemically important congeners of phosphorothioates and methylphosphonates. The authors have developed a convenient one-pot method to synthesize the set of ribonucleoside (A, U, G, and C) 5{prime}-({alpha}-P-borano)triphosphates. Phosphitylation of the 2{prime},3{prime}-protected ribonucleoside with 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one gives the 5{prime}-phosphite intermediate 2 which undergoes in situ substitution in the presence of pyrophosphate to give the cyclic intermediate, P{sup 2},P{sup 3}-dioxo-P{sup 1}-ribonucleosidylcyclotriphosphate 3. Immediate oxidation of compound 3 with amine{center_dot}borane complex results in ribonucleoside 5{prime}-({alpha}-P-borano)cyclotriphosphate 4. Subsequent reaction of compound 4 with water followed by ammonium hydroxide yields the crude product as a diastereomeric mixture of ribonucleoside 5{prime}-({alpha}-P-borano)triphosphate 6. Pure compound 6 is isolated in 30--45% overall yield using ion-exchange chromatography. The separation of two diastereomers of ribonucleoside 5{prime}-({alpha}-P-borano)triphosphate 6 is achieved by reverse phase HPLC.
- Sponsoring Organization:
- USDOE, Washington, DC (United States)
- DOE Contract Number:
- FG05-94ER61882; FG02-97ER62376
- OSTI ID:
- 659067
- Journal Information:
- Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 17 Vol. 63; ISSN JOCEAH; ISSN 0022-3263
- Country of Publication:
- United States
- Language:
- English
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