Construction of an aminooxy derivative for RNA and DNA labeling.
We previously reported that the reactivity of a primary amine is increased by connecting the amine to an aromatic residue with an alkyl linker. This strategy was applied to the construction of a reagent that could form a covalent bond with an aldehyde group. We synthesized a new reagent that consisted of aminooxy and aromatic groups and biotin. The new reagent showed a higher reaction rate to apurinic/apyrimidinic (AP) sites in DNA than a conventional aldehyde-reactive probe (ARP). This reagent also efficiently reacted with 2', 3'-dialdehyde groups, which were generated by the oxidation of the 2', 3'-terminal vicinal hydroxy groups of RNA. The reaction efficiency of the reagent closely related to the structure of the target molecules. We describe the synthesis and chemical properties of the new reagent.
Komatsu
Yasuo
Y
Research Institute of Genome-based Biofactory, National Institute of Advanced Industrial Science & Technology (AIST Hokkaido), Toyohira-ku, Sapporo 062-8517, Japan. komatsu-yasuo@aist.go.jp
Kojima
Naoshi
N
Takebayashi
Toshie
T
Mikami
Akiko
A
Sugino
Maiko
M
Ohtsuka
Eiko
E
D001710:Biotin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D006898:Hydroxylamines / Q000138:chemical synthesis / Q000737:chemistry*; D015335:Molecular Probes / Q000138:chemical synthesis / Q000737:chemistry*; D012313:RNA / Q000737:chemistry*
D006898:Hydroxylamines; D015335:Molecular Probes; D012313:RNA; D001710:Biotin; D004247:DNA