Efficient synthesis of oligonucleotide conjugates on solid-support using an (aminoethoxycarbonyl)aminohexyl group for 5'-terminal modification.
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.
Kojima
Naoshi
N
Research Institute of Genome-based Biofactory, National Institute of Advanced Industrial Science and Technology, Tsukisamu-Higashi, Sapporo, Japan.
Takebayashi
Toshie
T
Mikami
Akiko
A
Ohtsuka
Eiko
E
Komatsu
Yasuo
Y
D020816:Amino Acid Motifs / Q000235:genetics; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D005998:Glycine / Q000031:analogs & derivatives; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000235:genetics
D009841:Oligonucleotides; C088137:aminoethoxyvinylglycine; D005998:Glycine