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Tailoring Peptide–Nucleotide Conjugates (PNCs) for Nucleotide Delivery in Bacterial Cells
Author(s) -
De Swarup,
Groaz Elisabetta,
Herdewijn Piet
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301781
Subject(s) - chemistry , peptide , nucleotide , moiety , linker , conjugate , combinatorial chemistry , oligopeptide , stereochemistry , rational design , biochemistry , peptide synthesis , oligonucleotide , dna , nanotechnology , gene , operating system , mathematical analysis , materials science , mathematics , computer science
Abstract The design and synthesis of peptide‐2′‐deoxythymidine‐5′‐ O ‐monophosphate conjugates as potential active delivery systems for nucleotides into auxotrophic E. coli strains is presented. A series of oligopeptides were allowed to react with 5′‐ O ‐(dibenzylphosphate)‐2′‐deoxythymidine or its suitably 3′‐derivatized analogues to give the relevant peptide–nucleotide adducts, by the formation of a biolabile chemical connection. Using strategies based on the principles of orthogonal protection and activation, rational variations were made to the linker and the peptide moiety in order to tune the metabolic stability of the conjugates.