The synthesis of protected 5′-amino2′, 5′-dideoxyribonucleoside-3′-O-phosphoramidites; applications of 5′-amino-oligodeoxyribonucleotides
Open Access
- 11 August 1987
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 15 (15) , 6181-6196
- https://doi.org/10.1093/nar/15.15.6181
Abstract
Synthetic routes to the four appropriately protected 5′-amino-2′, 5′-dideoxyribo-nucleoside-3′-O-(2-cyanoethyl N,N-diisopropylphosphoramidites) have been developed. The structures of all intermediates were confirmed by 13 C n.m.r. spectroscopy. These building blocks have been used to prepare 5′-amino-oligodeoxyribonucleotides, which can be coupled to a wide variety of compounds, in particular metal cluster derivatives, but also fluorophores and biotin derivatives, thus generating a variety of very useful probes. Brief mention is made of a tetrairidium cluster derivative of 5′-amino-d[CCGATATCGG], which has been cocrystallised with EcoRV, and will be used for electron microscopy studies.Keywords
This publication has 15 references indexed in Scilit:
- Detection of Specific DNA Sequences With Short Biotin-Labeled ProbesDNA, 1985
- Chemical and enzymatic biotin-labeling of oligodeoxyribonucleotidesNucleic Acids Research, 1985
- Biotin-labeled synthetic oligodeoxyribonucleotides: chemical synthesis and uses as hybridization probesNucleic Acids Research, 1985
- The synthesis of oligonucleotides containing an aliphatic amino group at the 5′ terminus: synthesis of fluorescent DNA primers for use in DNA sequence analysisNucleic Acids Research, 1985
- Polymer support oligonucleotide synthesis XVIII1.2): use ofβ-cyanoethyi-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final productNucleic Acids Research, 1984
- Synthesis of oligonucleotides containing the hypermodified base, alpha-putrescinylthymine.1983
- Aminonucleosides and their derivatives. IVISynthesis of the 3′-amino-3′-deoxynucleoside 5′-phosphatesNucleic Acids Research, 1979
- Halo sugar nucleosides. I. Iodination of the primary hydroxyl groups of nucleosides with methyltriphenoxyphosphonium iodideThe Journal of Organic Chemistry, 1970
- Purine nucleosides. XXV. Synthesis of certain derivatives of 5'-amino-5'-deoxy- and 5'-amino-2',5'-dideoxy-.beta.-D-ribofuranosylpurines as purine nucleotide analogsJournal of Medicinal Chemistry, 1969
- Synthese 5′‐substituierter AdenosinderivateEuropean Journal of Inorganic Chemistry, 1965