Synthesis and properties of oligonucleotide chimeras containing 5′-amino-2′-deoxy-2′-fluoroarabinonucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 22, Issue 5-8, 2003, Pages 1335-1338

  Viazovkina, Ekaterina ^a   Min, Kyung Lyum ^a   Galarneau, Annie ^a   Damha, Masad J ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

5 Amino 2 deoxy 2 fluoroarabinonucleosides; RNase H; Thermal stability

Indexed keywords

2 DEOXY 2' FLUORO BETA DEXTRO ARABINOSE; 5' AMINO 2' DEOXY 2' FLUOROARABINONUCLEOSIDE; ARABINONUCLEOSIDE; ARABINOSE DERIVATIVE; NUCLEOSIDE DERIVATIVE; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; RIBONUCLEASE H; UNCLASSIFIED DRUG;

CHIMERA; CONFERENCE PAPER; ESCHERICHIA COLI; HUMAN; NONHUMAN; NUCLEOTIDE METABOLISM; THERMOSTABILITY;

AMINES; ARABINONUCLEOSIDES; BASE SEQUENCE; FLUORINE; HUMANS; KINETICS; OLIGODEOXYRIBONUCLEOTIDES; RIBONUCLEASE H, CALF THYMUS; SUBSTRATE SPECIFICITY; THYMINE; URACIL;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 0141484675     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120022959     Document Type: Conference Paper

References (7)

1. Damha, M.J.; Wilds, C.J; Noronha, A.; Brukner, I.; Borkow, G.; Arion, D. ; Parniak, M.A. Hybrids of RNA and arabinonucleic acids (ANA and 2′F-ANA) are substrates of RNase H. J. Am. Chem. Soc. 1998, 120, 12,976-12,977.
2. 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.
3. Nottoli, E.M.; Lambert, J.B.; Letsinger, R.L. Study of conformational changes induced on substituting NH for O at C(5′) of thymidine nucleosides and nucleotides. J. Am. Chem. Soc. 1977, 99, 3486-3490.
4. Gryaznov, S.M.; Letsinger, R.L. Synthesis and properties of oligonucleotides containing aminodeoxythymidine units. Nucl. Acids Res. 1992, 20, 3403-3409.
5. Tetzlaff, C.N; Schwope, I.; Bleczinski, C.F.; Steinberg, J.A.; Richert, C. A convenient synthesis of 5′-amino-5′-deoxythymidine and preparation of peptide-DNA hybrids. Tetrahedron Letters 1998, 39, 4215-4218.
6. Harada, K.; Matulic-Adamic, J.; Price, R.W.; Schinazi, R.F.; Watanabe, K.; Fox, J.J. Nucleosides. 139. Synthesis and anticytomegalovirus and antiherpes simplex virus activity of 5′-modified analogues of 2′-fluoroarabinosylpyrimidine nucleosides. J. Med. Chem. 1987, 30, 226-229.
7. Min, K.; Viazovkina, E.; Galarneau, A.; Parniak, M.; Damha, M. Oligonucleotides comprised of alternating 2′-deoxy-2′ -fluoro-b-D-arabinonucleosides and D-2′-deoxyribonucleosides (2′F-ANA/DNA 'altimers') induce efficient RNA cleavage mediated by RNase H. Bioorg. Med. Chem. Lett. 2002, 12, 2651-2654.