A simple and efficient procedure for the synthesis of 5′-aminoalkyl oligodeoxynucleotides

Synthetic deoxyoligonucleotides have been 5′-aminoalkylated at the end of step-wise synthesis on the polymer support. This was achieved through the activation of the 5′-hydroxyl group as its 5′-imidazolyl derivative using carbonyldiimidazole, which was subsequently displaced with hexamethylene diara...

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Bibliographic Details
Published in:Nucleic acids research 1986-10, Vol.14 (20), p.7985-7994
Main Authors: Wachter, Leslie, Jablonslri, Jo-Ann, Ramachandran, Kuzhal L.
Format: Article
Language:English
Subjects:
5'-aminoalkyl oligodeoxynucleotides
Analytical, structural and metabolic biochemistry
Applied sciences
Biological and medical sciences
Biotin
Chemical Phenomena
chemicals
Chemistry
Chromatography, High Pressure Liquid
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Imidazoles
Nucleic acids
Nucleic bases, nucleotides
Oligodeoxyribonucleotides - chemical synthesis
Other techniques and industries
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Description
Summary:Synthetic deoxyoligonucleotides have been 5′-aminoalkylated at the end of step-wise synthesis on the polymer support. This was achieved through the activation of the 5′-hydroxyl group as its 5′-imidazolyl derivative using carbonyldiimidazole, which was subsequently displaced with hexamethylene diaraine to yield the title compound. The alkyl carbamate linkage thus generated withstands the deprotection conditions used in oligonucleotide synthesis. Purification by gel electrophoresis and further derivatization at the 5′-amino group with N-hydroxysuccinimidobiotin is described.
ISSN:0305-1048
1362-4962
DOI:10.1093/nar/14.20.7985