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Synthesis of a Pyridoxine–Peptide Based Delivery System for Nucleotides
Author(s) -
Marchand Arnaud,
Marchand Damien,
Busson Roger,
Marlière Philipe,
Herdewijn Piet
Publication year - 2007
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200790123
Subject(s) - pyridoxine , moiety , chemistry , nucleotide , peptide , residue (chemistry) , serine , stereochemistry , oligopeptide , aspartic acid , tetrapeptide , combinatorial chemistry , biochemistry , amino acid , phosphorylation , gene
Abstract As a first step in the development of a nucleotide delivery system making use of oligopeptide permease, we have synthesized pyridoxine–peptide–nucleotide conjugates. The nucleotides are bonded on serine residues. The peptides terminate with a pyroglutamate residue. In the first example, the pyridoxine moiety is connected at the end of the peptides, while, in the second example, the pyridoxine moiety is bonded at an aspartic acid residue in a middle position of the peptide. Nucleotides are introduced as phosphoramidites. The synthetic strategy involves a series of protection, deprotection, and coupling reactions, and integrates peptide, nucleotide, and pyridoxine chemistry. The final deprotection step was carried out in basic conditions using 10% K 2 CO 3 in MeOH.