A Convenient Solid-Phase Method for the Synthesis of Novel Oligonucleotide-Folate Conjugates (original) (raw)
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AbstractÐA convenient`on line' solid-phase synthesis of oligonucleotides conjugated at the 3 H -end with peptides by means of a polymeric support linking the ®rst nucleoside via the base has been developed. A 17-mer designed for antisense experiments against HIV-1, linking at the 3 H -terminus the tripeptide Gly-Gly-His, was prepared in good yields and characterized by MALDI-TOF mass spectrometry. #
Total Stepwise SolidPhase Synthesis of Oligonucleotide(3‘→ N )Peptide Conjugates
Organic Letters, 2002
An efficient total stepwise solid-phase synthesis of oligonucleotide-(3′fN)-peptide conjugates is described that makes use of either a controlled pore glass support or macroporous polystyrene beads. Extending our previous homoserine linker approach, we prepared a range of conjugates containing one of four different cell or nuclear penetration peptides together with oligonucleotides containing 2′-deoxynucleoside or 2′-Omethylribonucleoside phosphodiesters, or gapmers containing 2′-deoxyphosphorothioates. The route also allows incorporation of a fluorescent label within the conjugate for cell uptake studies.
New developments in the synthesis of oligonucleotide-peptide conjugates
Nucleosides Nucleotides & Nucleic Acids, 2007
The stability of oligodeoxynucleotides to trifluoroacetic acid is studied. Pyrimidine oligonu- cleotides were stable in the conditions used for the removal of t-butyl groups. Oligonucleotide-3'- peptide conjugates carrying pyrimidine oligonucleotides are prepared stepwise using peptide-supports and Fmoc, t-butyl strategy. Using this strategy we have prepared an oligonucleotide-peptide conju- gate containing as peptide the leucine-rich fragment of FOS, a transcription factor
ChemInform Abstract: Chemical Strategies for Oligonucleotide-Conjugate Synthesis
ChemInform, 2008
Oligonucleotide conjugates have found numerous applications in the field of diagnostics and therapeutics. Structurally diverse oligonucleotide conjugates have been prepared and evaluated for various applications. Research efforts have focused on the development of synthetic procedures to accomplish efficient oligonucleotide conjugation with different target molecules. Both on-support and solution-phase coupling procedures have been used to conjugate oligonucleotides. This review gives an account of major synthetic approaches available to prepare covalent oligonucleotide conjugates with diverse target molecules.
Organic & Biomolecular Chemistry, 2004
An efficient method for synthesis of oligonucleotide 2′-conjugates via amide bond formation on solid phase is described. Protected oligonucleotides containing a 2′-O-carboxymethyl group were obtained by use of a novel uridine 3′-phosphoramidite, where the carboxylic acid moiety was introduced as its allyl ester. This protecting group is stable to the conditions used in solid-phase oligonucleotide assembly, but easily removed by Pd(0) and morpholine treatment. 2′-O-Carboxymethylated oligonucleotides were then efficiently conjugated on a solid support under normal peptide coupling conditions to various amines or to the N-termini of small peptides to give products of high purity in good yield. The method is well suited in principle for the preparation of peptide-oligonucleotide conjugates containing an amide linkage between the 2′-position of an oligonucleotide and the N-terminus of a peptide. † Electronic supplementary information (ESI) available: MALDI-TOF spectra. See
Nucleosides, Nucleotides and Nucleic Acids, 1995
A rapid method is described for the covalent anchoring of appropriately protected 2'deoxyribonucleoside-3'-O-succinates to LCAA-CPG, widely used support for solid phase oligonucleotide synthesis. The method involves the reaction of nucleoside-3'-O-succinates with aminoalkyl functions of the support in the presence of improved and commercially available condensing reagent, TBTU or TPP-DTNP to generate fully functionalised polymer supports with excellent nucleoside loadings.
Helvetica Chimica Acta, 2002
Dedicated to Prof. Dr. Wolfgang Pfleiderer on the occasion of his 75th birthday Oligodeoxynucleotide conjugates 1-15 carrying anchoring groups such as amino, thiol, pyrrole, and carboxyl groups were prepared. A post-synthetic modification protocol was developed. In this method 2'-deoxy-O 4 -(p-nitrophenyl)uridine-3-phosphoramidite was prepared and incorporated in oligonucleotides. Following assembly of the sequence, the modified nucleoside was made to react with different amines carrying the anchoring groups. At the same time protecting groups were removed to yield the desired oligonucleotide conjugates. In a second approach, amino, thiol and carboxylic groups were introduced into the 3'-end of the oligonucleotides by preparing solid supports loaded with the appropriate amino acids. Oligonucleotide-gold conjugates were prepared and their binding properties were examined.
A new universal solid support for oligonucleotide synthesis
Tetrahedron, 1999
was prepared and attached to a controlled pore glass to generate a new universal solid support for oligonucleofide synthesis. This support is applicable for the preparation of all types of oligonucleotides as well as oligomers with unusual baselabile nucleosides.