Synthesis and triple helix formation by alternate strand recognition of oligonucleotides containing 3′-3′ phosphodiester bonds

被引:19
作者
De Napoli, L
Messere, A
Montesarchio, D
Pepe, A
Piccialli, G
Varra, M
机构
[1] Univ Naples Federico II, Dipartimento Chim Organ & Biol, I-80134 Naples, Italy
[2] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy
关键词
D O I
10.1021/jo970589t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
ODNs containing a 3'-3' phosphodiester junction have been conveniently synthesized through a solid phase procedure involving only 3'-phosphoramidite nucleosides, starting from a modified support linking the first nucleotide through the base. Thermal denaturation studies showed that 16-mers with this inversion of polarity cooperatively bound to 5'-(purine)(m)(pyrimidine)(n)-3'-type duplexes by specific recognition of the oligopurine domains alternately on the two DNA strands. The nature of the 3'-3' junction and nearest neighbors affected the stability of the resulting triplexes.
引用
收藏
页码:9024 / 9030
页数:7
相关论文
共 32 条
[1]  
[Anonymous], 1970, Handbook of Biochemistry
[2]   5'-5'-TETHERED OLIGONUCLEOTIDES VIA NUCLEIC BASES - A POTENTIAL NEW SET OF COMPOUNDS FOR ALTERNATE STRAND TRIPLE-HELIX FORMATION [J].
ASSELINE, U ;
THUONG, NT .
TETRAHEDRON LETTERS, 1994, 35 (29) :5221-5224
[3]   OLIGONUCLEOTIDES TETHERED VIA NUCLEIC BASES - A POTENTIAL NEW SET OF COMPOUNDS FOR ALTERNATE STRAND TRIPLE-HELIX FORMATION [J].
ASSELINE, U ;
THUONG, NT .
TETRAHEDRON LETTERS, 1993, 34 (26) :4173-4176
[4]   A POLYMER-NUCLEOTIDE LINKAGE USEFUL FOR THE SOLID-PHASE SYNTHESIS OF CYCLIC OLIGODEOXYRIBONUCLEOTIDES [J].
BARBATO, S ;
DENAPOLI, L ;
MAYOL, L ;
PICCIALLI, G ;
SANTACROCE, C .
TETRAHEDRON, 1989, 45 (14) :4523-4536
[5]   SOLID-PHASE SYNTHESIS OF CYCLIC OLIGODEOXYRIBONUCLEOTIDES [J].
BARBATO, S ;
DENAPOLI, L ;
MAYOL, L ;
PICCIALLI, G ;
SANTACROCE, C .
TETRAHEDRON LETTERS, 1987, 28 (46) :5727-5728
[6]  
Bayer E., 1991, ANGEW CHEM, V103, P117
[7]   RECOGNITION OF DOUBLE HELICAL DNA BY ALTERNATE STRAND TRIPLE HELIX FORMATION [J].
BEAL, PA ;
DERVAN, PB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :4976-4982
[8]  
CARUTHERS MH, 1987, BIOPHOSPHATES THEIR, P3
[9]   AUTOMATED SYNTHESIS OF CYCLIC OLIGODEOXYRIBONUCLEOTIDES VIA PHOSPHORAMIDITE METHOD [J].
CONTE, MR ;
MAYOL, L ;
MONTESARCHIO, D ;
PICCIALLI, G ;
SANTACROCE, C .
NUCLEOSIDES & NUCLEOTIDES, 1993, 12 (3-4) :351-358
[10]   AUTOMATED SOLID-PHASE SYNTHESIS OF CYCLIC OLIGONUCLEOTIDES - A FURTHER IMPROVEMENT [J].
DENAPOLI, L ;
GALEONE, A ;
MAYOL, L ;
MESSERE, A ;
MONTESARCHIO, D ;
PICCIALLI, G .
BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (10) :1325-1329