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  • Efficient synthesis of oligonucleotide conjugates on solid-support using an (aminoethoxycarbonyl)aminohexyl group for 5'-terminal modification.

Efficient synthesis of oligonucleotide conjugates on solid-support using an (aminoethoxycarbonyl)aminohexyl group for 5'-terminal modification.

Bioorganic & medicinal chemistry letters (2009-03-24)
Naoshi Kojima, Toshie Takebayashi, Akiko Mikami, Eiko Ohtsuka, Yasuo Komatsu
ABSTRACT

Solid-support conjugation at the 5'-terminal primary amine of oligonucleotides is a convenient and powerful method for introducing various functional groups. However, conventional aliphatic amines do not necessarily provide conjugates with sufficient yields. To improve the modification efficacy, we used the amino-linker (aminoethoxycarbonyl)aminohexyl group (ssH-linker), for solid-support conjugation. In the ssH-linker terminal modification, reactive free amino group could be easily presented onto a solid-support due to rapid removal of the amino-protecting group, and activated amino acids or cholesterol molecules could be covalently connected more efficiently than to typical 6-aminohexyl-linkers. Based on these results, the ssH-linker can be a useful terminal modification for the solid-support conjugation of functional molecules.

MATERIALS
Product Number
Brand
Product Description

Supelco
Aminoethoxyvinyl glycine hydrochloride, PESTANAL®, analytical standard
Sigma-Aldrich
(S)-trans-2-Amino-4-(2-aminoethoxy)-3-butenoic acid hydrochloride, ≥93% (AT)
Sigma-Aldrich
(S)-trans-2-Amino-4-(2-aminoethoxy)-3-butenoic acid hydrochloride, BioReagent, suitable for plant cell culture, powder