Incorporation of hexose nucleoside analogues into oligonucleotides: synthesis, base-pairing properties and enzymatic stability.
Oligonucleotides containing 1-(2,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (2) and 1-(3,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (3) were synthesized on a solid support using the phosphoramidite approach. The properties of these oligonucleotides were compared with the earlier reported characteristics of oligonucleotides containing 1-(2,3-dideoxy-beta-D-erythro-hexopyranosyl) thymine (1). The order in enzymatic stability of end-substituted oligonucleotides is 3 greater than 1 much greater than 2. The hybridization properties of the modified oligonucleotides are in reverse order: 2 much greater than 1 greater than 3.
Augustyns
K
K
Laboratory of Pharmaceutical Chemistry, Rega Institute for Medical Research, Leuven.
Vandendriessche
F
F
Van Aerschot
A
A
Busson
R
R
Urbanke
C
C
Herdewijn
P
P
D000469:Alkaline Phosphatase / Q000378:metabolism; D001482:Base Composition; D001483:Base Sequence; D006601:Hexoses; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009691:Nucleic Acid Denaturation; D009705:Nucleosides; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D043264:Phosphodiesterase I; D010727:Phosphoric Diester Hydrolases / Q000378:metabolism; D013329:Structure-Activity Relationship; D013941:Thymine
D006601:Hexoses; D007202:Indicators and Reagents; D009705:Nucleosides; D009841:Oligonucleotides; D000469:Alkaline Phosphatase; D010727:Phosphoric Diester Hydrolases; D043264:Phosphodiesterase I; D013941:Thymine