Nucleosides and Nucleotides. 135. DNA Duplex and Triplex formation and Resistance to Nucleolytic Degradation of Oligodeoxynucleotides Containing syn-Norspermidine at the 5-Position of 2'-Deoxyuridine
- 1 January 1995
- journal article
- research article
- Published by American Chemical Society (ACS) in Bioconjugate Chemistry
- Vol. 6 (1) , 54-61
- https://doi.org/10.1021/bc00031a005
Abstract
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 triplex 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'.Keywords
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