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- Title
A New and Efficient Method for Synthesis of 5′-Conjugates of Oligonucleotides through Amide-Bond Formation on Solid Phase.
- Authors
Kachalova, Anna V.; Stetsenko, Dmitry A.; Romanova, Elena A.; Tashlitsky, Vadim N.; Gait, Michael J.; Oretskaya, Tatiana S.
- Abstract
An efficient method for synthesis of oligonucleotide 5′-conjugates through amide-bond formation on solid phase is described. Protected oligonucleotides containing a 5′-carboxylic acid function were obtained by use of a novel non-nucleosidic phosphoramidite building block, where the carboxylic acid moiety was protected by a 2-chlorotrityl group. The protecting group is stable to the phosphoramidite coupling conditions used in solid-phase oligonucleotide assembly, but is easily deprotected by mild acidic treatment. The protecting group may be removed also by ammonolysis. 5′-Carboxylate-modified oligonucleotides were efficiently conjugated on solid support under normal peptide-coupling conditions to various amines or to the N-termini of small peptides to yield products of high purity. The method is well-suited in principle for the synthesis of peptide-oligonucleotide conjugates containing an amide linkage between the 5′-end of an oligonucleotide and the N-terminus of a peptide.
- Publication
Helvetica Chimica Acta, 2002, Vol 85, Issue 8, p2409
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/1522-2675(200208)85:8<2409::AID-HLCA2409>3.0.CO;2-P