1608114-29-9Relevant academic research and scientific papers
Synthesis of new biocarrier-nucleotide systems for cellular delivery in bacterial auxotrophic strains
De, Swarup,Groaz, Elisabetta,Maiti, Mohitosh,Pezo, Valérie,Marlière, Philippe,Herdewijn, Piet
, p. 8843 - 8851 (2014)
In search for a delivery approach for thymidine monophosphate (TMP) in bacterial cells, we have synthesized a series of conjugates of TMP with biotin having an oxymethyleneoxy ester, a carboxy ester, and different carboxamide linkers between the carboxyl group of biotin and the 3′-OH group of TMP. The synthetic strategy starts from 5′-O-(dibenzylphosphate)-thymidine having the linkers already connected at the 3′-position. Likewise, kanamycin A was linked at the 3′-position of TMP using a carbamoyl or thioethyl carbamoyl group. None of the conjugates were able to sustain growth of a ΔthyA, ΔphoA Escherichia coli strain.
Tailoring peptide-nucleotide conjugates (PNCs) for nucleotide delivery in bacterial cells
De, Swarup,Groaz, Elisabetta,Herdewijn, Piet
, p. 2322 - 2348 (2014/04/17)
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.
