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N 7 ‐DNA: Base‐Pairing Properties of N 7 ‐(2′‐Deoxy‐ β ‐ D ‐ erythro ‐pentofuranosyl)‐Substituted Adenine, Hypoxanthine, and Guanine in Duplexes with Parallel Chain Orientation
Author(s) -
Seela Frank,
Leonard Peter
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19981216)81:12<2244::aid-hlca2244>3.0.co;2-i
Subject(s) - chemistry , phosphoramidite , guanine , oligonucleotide , nucleobase , cytosine , hypoxanthine , stereochemistry , nucleic acid , guanosine , dna , base pair , deoxyribonucleotide , diastereomer , nucleotide , duplex (building) , biochemistry , gene , enzyme
Oligonucleotides containing N 7 ‐(2′‐deoxy‐ β ‐ D ‐ erythro ‐pentofuranosyl)adenine ( 1 ), ‐hypoxanthine ( 2 ), and ‐guanine ( 3 ) were synthesized on solid‐phase using phosphonate and phosphoramidite chemistry. As part of the synthesis of compound 2 , the nucleobase‐anion glycosylation of various 6‐alkoxypurines with 2‐deoxy‐3,5‐di‐ O ‐(4‐toluoyl)‐ α ‐ D ‐ erythro ‐pentofuranosyl chloride ( 5 ) was investigated. The duplex stability of oligonucleotides containing N 7 ‐glycosylated purines opposite to regular pyrimidines was determined, and thermodynamic data were calculated from melting profiles. Oligodeoxyribonucleotide duplexes containing N 7 ‐glycosylated adenine⋅T d or N 7 ‐glycosylated guanine⋅C d base pairs are more stable in the case of parallel strand orientation than in the case of antiparallel chains.