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Synthesis of Aldehyde‐Linked Nucleotides and DNA and Their Bioconjugations with Lysine and Peptides through Reductive Amination
Author(s) -
Raindlová Veronika,
Pohl Radek,
Hocek Michal
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103270
Subject(s) - reductive amination , tripeptide , chemistry , nucleotide , lysine , cytidine , dna , aqueous solution , aldehyde , combinatorial chemistry , organic chemistry , biochemistry , peptide , amino acid , catalysis , enzyme , gene
5‐(5‐Formylthienyl)‐, 5‐(4‐formylphenyl)‐ and 5‐(2‐fluoro‐5‐formylphenyl)cytosine 2′‐deoxyribonucleoside mono‐ ( dC R MP ) and triphosphates ( dC R TP ) were prepared by aqueous Suzuki–Miyaura cross‐coupling of 5‐iodocytosine nucleotides with the corresponding formylarylboronic acids. The dC R TP s were excellent substrates for DNA polymerases and were incorporated into DNA by primer extension or PCR. Reductive aminations of the model dC R MP s with lysine or lysine‐containing tripeptide were studied and optimized. In aqueous phosphate buffer (pH 6.7) the yields of the reductive aminations with tripeptide III were up to 25 %. Bioconjugation of an aldehyde‐containing DNA with a lysine‐containing tripeptide was achieved through reductive amination in yields of up to 90 % in aqueous phosphate buffer.