In:
Helvetica Chimica Acta, Wiley, Vol. 77, No. 3 ( 1994-05-11), p. 597-607
Abstract:
The synthesis of oligonucleotides containing 7‐(2‐deoxy‐β ‐ D ‐ erythro ‐pentofuranosyl)adenine ( N 7 A d ; 1 ) is described. Compound 1 was obtained from the precursor 4‐amino‐1 H ‐imidazole‐5‐carbonitrile 2‐deoxyribonucleoside 6 and was found to be much more labile than A d . The N 6 ‐benzoyl protecting group (see 8 ) destabilized the N‐glycosylic bond further and was difficult to remove by NH 3 ‐catalyzed hydrolysis. Therefore, a (dimethyl‐amino)methylidene residue was introduced (→ 9 ). Amidine 9 was blocked at OHC(5′) with the dimethoxytrityl residue ((MeO) 2 Tr), and phosphonate 4 as well as phosphoramidite 5 were prepared under standard conditions. Phosphonate 4 was employed in solid‐phase oligonucleotide synthesis. Homooligonucleotides as well as self‐complementary oligonucleotides were prepared. The oligomer d[( N 7 A) 11 ‐A] ( 11 ) formed a duplex with d(T 12 ) ( 13 ). Antiparallel chain polarity and reverse Watson‐Crick base pairing was deduced from duplex formation of the self‐complementary d[( N 7 A) 8 ‐T 8 ] ( 14 ).
Type of Medium:
Online Resource
ISSN:
0018-019X
,
1522-2675
DOI:
10.1002/hlca.19940770302
Language:
English
Publisher:
Wiley
Publication Date:
1994
detail.hit.zdb_id:
74-7
detail.hit.zdb_id:
1475013-2
