NUCLEOSIDES AND NUCLEOTIDES .135. DNA DUPLEX AND TRIPLER FORMATION AND RESISTANCE TO NUCLEOLYTIC DEGRADATION OF OLIGODEOXYNUCLEOTIDES CONTAINING SYN-NORSPERMIDINE AT THE 5-POSITION OF 2'-DEOXYURIDINE

被引:41
作者
NARA, H [1 ]
ONO, A [1 ]
MATSUDA, A [1 ]
机构
[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,KITA KU,SAPPORO,HOKKAIDO 060,JAPAN
关键词
D O I
10.1021/bc00031a005
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A novel 2'-deoxyuridine analogue with syn-norspermidine at the 5-position, 5-[4-[N,N-bis(3-amino-propyl)amino]butyl]-2'-deoxyuridine (1), has been synthesized from 5-iodo-2'-deoxyuridine. This nucleoside 1 was incorporated into heptadecadeoxynucleotides 5'-d[1(MT)(8)]-3' and 5'-[(TM)(4)1(MT)(4)]-3' (M = 5-methyl-2'-deoxycytidine). The triamine group stabilized duplex and tripler formation of the heptadecadeoxynucleotides with a complementary strand and a target duplex, respectively. The oligonucleotides containing 1 were more resistant to nuclease P1 and snake venom phosphodiesterase than an unmodified heptadecadeoxynucleotide, 5'-d[T(MT)(8)]-3'.
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页码:54 / 61
页数:8
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