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Synthesis of Oligonucleotides Containing 2′‐Deoxyisoguanosine and 2′‐Deoxy‐5‐methylisocytidine Using Phosphoramidite Chemistry
Author(s) -
Jurczyk Simona C.,
Kodra Janos T.,
Rozzell J. David,
Benner Steven A.,
Battersby Thomas R.
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/hlca.19980810502
Subject(s) - phosphoramidite , chemistry , moiety , oligonucleotide , oligonucleotide synthesis , solid phase synthesis , combinatorial chemistry , stereochemistry , biochemistry , dna , peptide
The synthesis of oligonucleotides containing 2′‐deoxy‐5‐methylisocytidine and 2′‐deoxyisoguanosine using phosphoramidite chemistry in solid‐phase oligonucleotide synthesis is described. Supporting previous observations, the N , N ‐diisobutylformamidine moiety was found to be a far superior protecting group than N ‐benzoyl for 2′‐deoxy‐5‐methylisocytidine. 2′‐Deoxy‐ N 2 ‐[(diisobutylamino)methylidene]‐5′‐(4,4′‐dimethoxytityl)‐5‐methylisocytidine 3′‐(2‐cyanoethyl diisopropylphosphoramidite) ( 1c ) incorporated multiple consecutive residues during a standard automated synthesis protocol with a coupling efficiency > 99% according to dimethoxytrityl release. Extending coupling times of the standard protocol to ≥ 600s using 2′‐deoxy‐ N 6 ‐[(diisobutylamino)methylidene]‐5′‐ O ‐(dimethoxytrityl)‐ O 2 ‐(diphenylcarbamoyl)isoguanosine, 3′‐(2‐cyanoethyl diisopropylphosphoramidite) ( 7e ) led to successful incorporation of multiple consecutive 2′‐deoxyisoguanosine bases with a coupling efficiency > 97% according to dimethoxytrityl release.