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8‐Aza‐7‐deaza‐2′‐deoxyguanosine: Phosphoramidite synthesis and properties of octanucleotides
Author(s) -
Seela Frank,
Driller Hansjürgen
Publication year - 1988
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/hlca.19880710530
Subject(s) - chemistry , phosphoramidite , phosphodiester bond , deoxyguanosine , oligonucleotide , cleavage (geology) , oligomer , guanosine , stereochemistry , solid phase synthesis , dna , deoxyribonucleotide , oligonucleotide synthesis , hydrolysis , biochemistry , polymer chemistry , peptide , rna , geotechnical engineering , fracture (geology) , engineering , gene
Base‐modified octanucleotides derived from d(G1–G2–A–A–T–T–C–C–) ( 11 ) but containing 8‐aza‐7‐deaza‐2′‐deoxyguanosine ( 2 ) instead of 2′‐deoxyguanosine ( 1 ) have been prepared by solid‐phase synthesis employing P(III) chemistry. Isobutyrylation of 2 , followed by 4, 4′‐dimethoxytritylation and subsequent phosphitylation yielded the methyl or the cyanoethyl phosphoramidites 6a or 6b , respectively. They were used as building blocks in automated DNA synthesis. The resulting octanucleotides 12–14 containing 2 showed increased T m values compared to the parent oligomer 11 . The oligomers 11 – 14 were employed as sequence‐specific probes in endo‐deoxyribonuclease Eco RI oligonucleotide recognition. Whereas displacement of dG‐2 (enzymic cleavage site of 11 ) abolished phosphodiester hydrolysis, replacement of dG‐1 enhanced the cleavage rate compared to 11 .