Open AccessAminooxy Click Chemistry as a Tool for Bis-homo and Bis-hetero Ligand Conjugation to Nucleic Acids
Author(s) -
Dhrubajyoti Datta,
Shohei Mori,
Mimouna Madaoui,
Kelly Wassarman,
Ivan Zlatev,
Muthiah Manoharan
Publication year - 2022
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.2c00988
Subject(s) - chemistry , click chemistry , oligonucleotide , nucleic acid , combinatorial chemistry , ligand (biochemistry) , nucleoside , stereochemistry , biochemistry , dna , receptor
An aminooxy click chemistry (AOCC) strategy was used to synthesize nucleoside building blocks for incorporation during solid-support synthesis of oligonucleotides to enable bis-homo and bis-hetero conjugation of various biologically relevant ligands. The bis-homo aminooxy conjugation leads to bivalent ligand presentation, whereas the bis-hetero conjugation allows the placement of different ligands with either the same or different chemical linkages. This facile synthetic methodology allows introduction of two different ligands with different biological functions simultaneously.