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These uptake pathways may be utilized for the delivery of biologically relevant molecules into cells. Indeed, it was recently reported that vitamin\u2005B<jats:sub>12<\/jats:sub> transported an antisense peptide nucleic acid (PNA) into <jats:italic>Escherichia coli<\/jats:italic> and <jats:italic>Salmonella<\/jats:italic> Typhimurium cells. The present studies indicate that the conjugation site of PNA to vitamin\u2005B<jats:sub>12<\/jats:sub> has an impact on PNA transport into bacterial cells. Toward this end, a specifically designed PNA oligomer has been tethered at various positions of vitamin\u2005B<jats:sub>12<\/jats:sub> (central Co, R<jats:sub>5\u2032<\/jats:sub>\u2010OH, <jats:italic>c<\/jats:italic> and <jats:italic>e<\/jats:italic> amide chains, <jats:italic>meso<\/jats:italic> position, and at the hydroxy group of cobinamide) by using known or newly developed methodologies and tested for the uptake of the synthesized conjugates by <jats:italic>E. coli<\/jats:italic>. Compounds in which the PNA oligonucleotide was anchored at the R<jats:sub>5\u2032<\/jats:sub>\u2010OH position were transported more efficiently than that of other compounds tethered at the peripheral positions around the corrin ring. Of importance is the fact that, contrary to mammalian organisms, <jats:italic>E. coli<\/jats:italic> also takes up cobinamide, which is an incomplete corrinoid. This selectivity opens up ways to fight bacterial infections.<\/jats:p>","DOI":"10.1002\/chem.201804304","type":"journal-article","created":{"date-parts":[[2018,10,5]],"date-time":"2018-10-05T22:30:04Z","timestamp":1538778604000},"page":"18772-18778","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Does a Conjugation Site Affect Transport of Vitamin\u2005B<sub>12<\/sub>\u2013Peptide Nucleic Acid Conjugates into Bacterial Cells?"],"prefix":"10.1002","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8347-5498","authenticated-orcid":false,"given":"Aleksandra J.","family":"Wierzba","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry Polish Academy of Sciences  Kasprzaka 44\/52 01-224 Warsaw Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ksenia","family":"Maximova","sequence":"additional","affiliation":[{"name":"Centre of New Technologies University of Warsaw 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