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.
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'.
Nara
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Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Ono
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Matsuda
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D004247:DNA / Q000737:chemistry / Q000378:metabolism; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D009691:Nucleic Acid Denaturation; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009711:Nucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D043264:Phosphodiesterase I; D010727:Phosphoric Diester Hydrolases / Q000737:chemistry; D015719:Single-Strand Specific DNA and RNA Endonucleases / Q000737:chemistry; D013095:Spermidine / Q000031:analogs & derivatives / Q000032:analysis / Q000737:chemistry
C093043:5-(4-(N,N-bis(3-aminopropyl)amino)butyl)-2'-deoxyuridine; D009705:Nucleosides; D009711:Nucleotides; D009841:Oligonucleotides; C006760:norspermidine; D004247:DNA; D015719:Single-Strand Specific DNA and RNA Endonucleases; D010727:Phosphoric Diester Hydrolases; D043264:Phosphodiesterase I; C470790:phosphodiesterase I, snake venom; D013095:Spermidine; D003857:Deoxyuridine