In:
Helvetica Chimica Acta, Wiley, Vol. 81, No. 5-8 ( 1998-01), p. 793-811
Abstract:
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.
Type of Medium:
Online Resource
ISSN:
0018-019X
,
1522-2675
DOI:
10.1002/hlca.v81:5/8
DOI:
10.1002/hlca.19980810502
Language:
English
Publisher:
Wiley
Publication Date:
1998
detail.hit.zdb_id:
74-7
detail.hit.zdb_id:
1475013-2
