Versatile strategy for oligonucleotide derivatization. Introduction of lanthanide(III) chelates to oligonucleotides

被引:55
作者
Hovinen, J [1 ]
Hakala, H [1 ]
机构
[1] Wallac Oy, PerkinElmer Life Sci, FIN-20101 Turku, Finland
关键词
D O I
10.1021/ol016093m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Novel nucleosidic phosphoramidite blocks were synthesized by a Mitsunobu reaction between 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine and a primary alcohol containing a conjugate group in its structure (a protected functional group, an organic dye, or a precursor of a lanthanide(III) chelate) followed by phosphitylation. They were used in machine-assisted DNA synthesis in the standard manner. A slighty modified deprotection procedure was used for the preparation of oligonucleotide conjugates tethered to lanthanide(Ill) chelates. For the latter application one non-nucleosidic block was also synthesized.
引用
收藏
页码:2473 / 2476
页数:4
相关论文
共 12 条
[1]   THE SYNTHESIS OF MODIFIED OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH AND THEIR APPLICATIONS [J].
BEAUCAGE, SL ;
IYER, RP .
TETRAHEDRON, 1993, 49 (28) :6123-6194
[2]  
BEAUCAGE SL, 1999, SYNLETT, P1667
[3]   Synthesis of polyphosphorylated AZT derivatives for the development of specific enzyme immunoassays [J].
Brossette, T ;
Le Faou, A ;
Goujon, L ;
Valleix, A ;
Créminon, C ;
Grassi, J ;
Mioskowski, C ;
Lebeau, L .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5083-5090
[4]   EUROPIUM-LABELED OLIGONUCLEOTIDE HYBRIDIZATION PROBES - PREPARATION AND PROPERTIES [J].
DAHLEN, P ;
LIUKKONEN, L ;
KWIATKOWSKI, M ;
HURSKAINEN, P ;
IITIA, A ;
SIITARI, H ;
YLIKOSKI, J ;
MUKKALA, VM ;
LOVGREN, T .
BIOCONJUGATE CHEMISTRY, 1994, 5 (03) :268-272
[5]   CHEMICALLY MODIFIED OLIGONUCLEOTIDES AS PROBES AND INHIBITORS [J].
ENGLISCH, U ;
GAUSS, DH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (06) :613-629
[6]   EUROPIUM AS A LABEL IN TIME-RESOLVED IMMUNOFLUOROMETRIC ASSAYS [J].
HEMMILA, I ;
DAKUBU, S ;
MUKKALA, VM ;
SIITARI, H ;
LOVGREN, T .
ANALYTICAL BIOCHEMISTRY, 1984, 137 (02) :335-343
[7]  
Iyer RP, 1999, CURR OPIN MOL THER, V1, P344
[8]   SOLID-PHASE SYNTHESIS OF CHELATE-LABELED OLIGONUCLEOTIDES - APPLICATION IN TRIPLE-COLOR LIGASE-MEDIATED GENE ANALYSIS [J].
KWIATKOWSKI, M ;
SAMIOTAKI, M ;
LAMMINMAKI, U ;
MUKKALA, VM ;
LANDEGREN, U .
NUCLEIC ACIDS RESEARCH, 1994, 22 (13) :2604-2611
[9]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[10]   DEVELOPMENT OF LUMINESCENT EUROPIUM(III) AND TERBIUM(III) CHELATES OF 2,2'/6',2''-TERPYRIDINE DERIVATIVES FOR PROTEIN LABELING [J].
MUKKALA, VM ;
HELENIUS, M ;
HEMMILA, I ;
KANKARE, J ;
TAKALO, H .
HELVETICA CHIMICA ACTA, 1993, 76 (03) :1361-1378