9-(2-DEOXY-BETA-D-XYLOFURANOSYL)ADENINE AND 1-(2-DEOXY-BETA-D-XYLOFURANOSYL)THYMINE - PHOSPHORYLATION AND STABILITY

Autor(en): KRECMEROVA, M
SEELA, F
Stichwörter: Biochemistry & Molecular Biology; NUCLEOSIDE 5'-TRIPHOSPHATES
Erscheinungsdatum: 1992
Herausgeber: MARCEL DEKKER INC
Journal: NUCLEOSIDES & NUCLEOTIDES
Volumen: 11
Ausgabe: 7
Startseite: 1393
Seitenende: 1409
Zusammenfassung: 
Phosphorylation of 1-(2-deoxy-beta-D-xylofuranosyl)thymine (1) or 9-(2-deoxy-beta-D-xylofuranosyl)adenine (3) with phosphoryl chloride gives the cyclic 3',5'-phosphates (2 and 4a) but not the 5'-monophosphates 8a or 8b. The latter are obtained by phosphorylation of the 3'-O-benzoylated 2'-deoxy-beta-D-xylonucleosides (7a, b) and subsequent base-catalyzed removal of the benzoyl groups. Compound 3, as the parent dA, depurinates in acidic medium, a reaction which is facilitated in the case of the N6-benzoyl derivative 9b and reduced after the introduction of an amidine protecting group. N-Glycosylic bond hydrolysis of 2'-deoxy-beta-D-xylofuranosyl nucleosides is enhanced by a factor of two compared to 2'-deoxy-beta-D-ribofuranosyl nucleosides.
ISSN: 07328311
DOI: 10.1080/07328319208021182

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