Synthesis of two 6′α-fluorocarbocyclic nucleosides and incorporation into short segments of DNA

The 6′-fluorocarbocyclic nucleosides 1 and 2 have been synthesized from the bicyclic ketone 3 in 16 and 2% yield respectively. The nucleoside 1 has been incorporated into short chains of DNA using an automated synthesizer and these oligonucleotides have been shown to hybridize with (fluorine containing) complementary strands.

[1]  C. T. Evans,et al.  Potential use of carbocyclic nucleosides for the treatment of AIDS: chemo-enzymatic syntheses of the enantiomers of carbovir , 1992 .

[2]  S. Roberts,et al.  Fluorocarbocyclic nucleosides: synthesis and antiviral activity of 2'- and 6'-fluorocarbocyclic 2'-deoxy guanosines. , 1991, Journal of medicinal chemistry.

[3]  A. Holmes,et al.  A study of the regioselectivity of oxygen insertion in the Baeyer–Villiger oxidation of bicyclo[2.2.1]heptan-2-ones , 1991 .

[4]  D. Coe,et al.  The potential of carbocyclic nucleosides for the treatment of AIDS: synthesis of carbocyclic 6′-fluoro-2′,3′-dideoxythymidine , 1991 .

[5]  D. Coe,et al.  Preparation of nucleotide mimics with potent inhibitory activity against HIV reverse transcriptase , 1991 .

[6]  R. Storer,et al.  The potential for using carbocyclic nucleosides for the treatment of AIDS. Part 1. Preparation of some analogues for azidothymidine (AZT) , 1991 .

[7]  R. Moriarty,et al.  [Hydroxy(organosulfonyloxy)iodo]arenes in Organic Synthesis , 1990 .

[8]  C. Chavis,et al.  Sugar modified oligonucleotides. I. Carbo-oligodeoxynucleotides as potential antisense agents. , 1989, Biochemical and biophysical research communications.

[9]  G. Koser,et al.  Direct conversion of aliphatic carboxamides to alkylammonium tosylates with [hydroxy (tosyloxy) iodo] benzene , 1986 .

[10]  G. M. Loudon,et al.  Conversion of aliphatic amides into amines with [I,I-bis-(trifluoroacetoxy)iodo]benzene. II: Kinetics and mechanism , 1984 .

[11]  A. Radhakrishna,et al.  Conversion of aliphatic amides into amines with [I,I-bis(trifluoroacetoxy)iodo]benzene. 1. Scope of the reaction , 1984 .

[12]  J. Biernat,et al.  Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product. , 1984, Nucleic acids research.

[13]  J. Biernat,et al.  β-Cyanoethyl N,N-dialkylamino/N-morpholinomonochloro phosphoamidites, new phosphitylating agents facilitating ease of deprotection and work-up of synthesized oligonucleotides , 1983 .

[14]  R. Franz.  Ueber trishydrofluoride tertiaerer amine und ihren einsatz als fluorierungsmittel , 1980 .

[15]  R. Newton,et al.  Factors governing the ratio of isomeric oxabicyclo[3.2.1]octanones formed on Baeyer–Villiger oxidation of some 5-endo,7-anti-disubstituted bicyclo[2.2.1]heptan-2-ones , 1978 .

[16]  Y. Shealy,et al.  Acid-catalyzed cyclization of alkoxyacryloylureas to 2,4(1H,3H)pyrimidinediones , 1976 .

[17]  T. Maniatis,et al.  Chain length determination of small double- and single-stranded DNA molecules by polyacrylamide gel electrophoresis. , 1975, Biochemistry.

[18]  S. Roberts,et al.  Electrophilic bromination of bicyclo[3.2.0]hept-2-en-6-ones , 1975 .

[19]  W. Gratzer,et al.  Electrophoresis of RNA in formamide. , 1974, Biochemistry.

[20]  H. Khorana,et al.  Studies on Polynucleotides. XXIV.1 The Stepwise Synthesis of Specific Deoxyribopolynucleotides (4).2 Protected Derivatives of Deoxyribonucleosides and New Syntheses of Deoxyribonucleoside-3″ Phosphates3 , 1963 .

[21]  G. Shaw,et al.  32. Purines, pyrimidines, and glyoxalines. Part VII. New syntheses of 2-thiouracils and 2-thiothymines , 1958 .