Synthesis of sensitive oligodeoxynucleotides containing acylated cytosine, adenine, and guanine nucleobases.

ABSTRACT: The synthesis of oligodeoxynucleotides (ODNs) containing the base-labile N ⁶-acetyladenosine (6acA), N ²-acetylguanosine (2acG), and N4-methyoxycarbonyldeoxycytidine (4mcC), as well as up to four N ⁴-acetyldeoxycytidine (4acC) modifications is described. The 1,3-dithian-2-yl-methoxycarbonyl (Dmoc) group was used as the linker for solid phase synthesis, and the methyl Dmoc (meDmoc) group was used for the protection of the exo-amino groups of nucleobases. Deprotection and cleavage were achieved under non-nucleophilic conditions, under which the highly sensitive 4acC, 6acA, 2acG, and 4mcC were found completely stable. Among the modified nucleotides, 4acC has been found in nature, and proven beneficial to DNA duplex stability.

SUBMITTER: Chillar K 

PROVIDER: S-EPMC12288508 | biostudies-literature | 2025 Jun

REPOSITORIES: biostudies-literature