2021
DOI: 10.1021/acs.joc.1c02040
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Amino Acid–Viologen Hybrids: Synthesis, Cucurbituril Host–Guest Chemistry, and Implementation on the Production of Peptides

Abstract: We present herein the development of a series of viologen–amino acid hybrids, obtained in good yields either by successive alkylations of 4,4′-bipyridine, or by Zincke reactions followed by a second alkylation step. The potential of the obtained amino acids has been exemplified, either as typical guests of the curcubituril family of hosts (particularly CB[7]/[8]) or as suitable building blocks for the solution/solid-phase synthesis of two model tripeptides with the viologen core inserted within their sequences. Show more

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Cited by 2 publications
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“…1a and b). Viologen molecules form a set of organic molecules that have been used as linkers of nitrogenous bases and amino acids, 15 to anchor Ag nanoparticles to graphene oxide, 16 also widely used as building blocks of molecular machines, 17 and more recently in STM breaking junctions for molecular electronics studies. [18][19][20] Specifically, we consider the chiral HB viologen molecule, which has recently been synthesized.…”
Section: Chiral Moleculementioning
confidence: 99%
“…1a and b). Viologen molecules form a set of organic molecules that have been used as linkers of nitrogenous bases and amino acids, 15 to anchor Ag nanoparticles to graphene oxide, 16 also widely used as building blocks of molecular machines, 17 and more recently in STM breaking junctions for molecular electronics studies. [18][19][20] Specifically, we consider the chiral HB viologen molecule, which has recently been synthesized.…”
Section: Chiral Moleculementioning
confidence: 99%