A new synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)guanine (araF-G)

Nucleosides, Nucleotides and Nucleic Acids

Volumn 22, Issue 5-8, 2003, Pages 1339-1342

  Elzagheid, Mohamed I ^a   Viazovkina, Ekaterina ^a   Damha, Masad J ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Guanine arabinonucleoside; Nucleoside synthesis

Indexed keywords

2 CHLOROHYPOXANTHINE; 2 DEOXY 2 FLUORO 3,5 DI O BENZOYL ALPHA DEXTRO ARABINOFURANOSYL BROMIDE; 2' DEOXY 2' FLUORO BETA DEXTRO ARABINONUCLEOSIDE; 2' DEOXY 2' FLUOROARABINONUCLEOSIDE; 2' FLUORO 2 DEOXY BETA DEXTRO ARABINOFURANOSYLNUCLEOSIDE; 2' FLUROARABINONUCLEOSIDE PHOSPHORAMIDITE; 9 (2 DEOXY 2 FLUORO BETA DEXTRO ARABINOFURANOSYL)ADENINE; 9 (2 DEOXY 2 FLUORO BETA DEXTRO ARABINOFURANOSYL)GUANINE; ADENINE DERIVATIVE; AMMONIA; ANTISENSE OLIGODEOXYNUCLEOTIDE; ANTIVIRUS AGENT; ARABINONUCLEOSIDE; BROMINE DERIVATIVE; CARBOHYDRATE DERIVATIVE; CLEVUDINE; FIALURIDINE; FLUOROCARBOHYDRATE; GUANINE ARABINOSIDE; GUANINE DERIVATIVE; HYPOXANTHINE DERIVATIVE; METHANOL; NUCLEOSIDE DERIVATIVE; PHOSPHOAMINO ACID; THYMINE DERIVATIVE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

CONFERENCE PAPER; DRUG SYNTHESIS; NUCLEOTIDE METABOLISM; PHYSICAL CHEMISTRY;

ARABINONUCLEOSIDES; ARABINOSE; GUANINE; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE;

ANTHRACOTHORAX;

EID: 0141596220     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120022960     Document Type: Conference Paper

References (14)

1. (a) Wilds, C.J.; Damha, M.J. 2′-Deoxy-2′ -fluoroarabinonucleosides and oligonucleotides (2′F-ANA): synthesis and physicochemical studies. Nucl. Acids Res. 2000, 28, 3625-3635;
2. (b) Viazovkina, E.; Mangos, M.; Elzagheid, M.I.; Damha, M.J. Current Protocols in Nucleic Acid Chemistry 2002, 4.15.1-4.15.21.
3. Tann, C.H.; Brodfuehrer, P.R.; Brundidge, S.P.; Sapino, C., Jr.; Howell, H.G. Fluorocarbohydrates in synthesis. An efficient synthesis of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil (β-FIAU) and 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine (β-FMAU). J. Org. Chem. 1985, 50, 3644-3647.
4. Howell, H.G.; Brodfuehrer, P.R.; Brundidge, S.P.; Benigni, D.A.; Sapino, C., Jr. Antiviral nucleosides. A stereospecific, total synthesis of 2′-fluoro-2′-deoxy-β-D-arabinofuranosyl nucleosides. J. Org. Chem. 1988, 53, 85-88.
5. Maruyama, T.; Takamatsu, S.; Kozai, S.; Satoh, Y.; Izana, K. Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine bearing a selectively removable protecting group. Chem. Pharm. Bull. 1999, 47, 966-970.
6. (a) Elzagheid, M.I.; Viazovkina, E.; Masad, M.J. Synthesis of protected 2′-deoxy-2′-fluoro-β-D-arabinonucleosides. Synthesis of 2′-fluoroarabino nucleoside phosphoramidites and their use in the synthesis of 2′F-ANA. Current Protocols in Nucleic Acid Chemistry 2002, 1.7.1-1.7.19;
7. (b) Tennila, T.; Azhayeva, E.; Vepsalainen, J.; Laatikainen, R.; Azhayev, A.; Mikhailopulo, I. Oligonucleotides containing 9-(2-deoxy-2-fluoro-β -D-arabinofuranosyl)-adenine and -guanine: synthesis, hybridization and antisense properties. Nucleosides, Nucleotides and Nucl. Acids 2000, 19, 1861-1884.
8. Harnden, M.R.; Jarvest, R.L. An improved synthesis of the antiviral acyclonucleoside 9-(4-hydroxy-3-hydroxymethylbut-l-yl)guanine. Tetrahedron Lett. 1985, 26, 4265-4268.
9. Zemlicka, J. Synthesis and biological properties of 9-(2,4-dihydroxybutyl)adenine and guanine: new analogs of 9-(2,3-dihydroxypropyl)adenine (DHPA) and 9-(2-hydroxyethoxymethyl)guanine (acyclovir). Nucleosides, Nucleotides 1984, 3, 245-264.
10. Hanna, N.B.; Ramasamy, K.; Robins, R.K.; Revankar, G.R. Convenient synthesis of 2′-deoxy-6-thioguanosine, ara-guanine, ara-6-thioguanine and certain related purine nucleosides by the stereospecific sodium salt glycosylation procedure. J. Heterocylic Chem. 1988, 25, 1899-1903.
11. Cheriyan, U.O.; Ogilvie, K.K. Preparation of 9-β -D-arabinofuranosylguanine (araG). Nucleosides, Nucleotides 1982, 1, 233-237.
12. Ma, T.; Lin, J.-S.; GaryNewton, M.; Cheng, Y.-C.; Chu, C.K. Synthesis and anti-hepatitis B virus activity of 9-(2-deoxy-2-fluoro-β -L-arabinofuranosyl)purine nucleosides. J. Med. Chem. 1997, 40, 2750-2754.
13. Gaffney, B.L.; Marky, L.A.; Jones, R.A. The influence of the purine 2-amino group on DNA conformation and stability - II. Synthesis and physical characterization of d[CGT(2-NH2)ACG], d[CGU(2-NH2)ACG], and d[CGT(2-NH2)AT(2-NH2)ACG]. Tetrahedron 1984, 40, 3-13.
14. Robins, M.J.; Uznanski, B. Nucleic acid related compounds. 33. Conversions of adenosine and guanosine to 2,6-dichloro, 2-amino-6-chloro, and derived purine nucleosides. Can. J. Chem. 1981, 59, 2601-2607.