Amino Acid–Viologen Hybrids: Synthesis, Cucurbituril Host–Guest Chemistry, and Implementation on the Production of Peptides

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 gu...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 1; pp. 760 - 764
Main Authors Barravecchia, Liliana, Neira, Iago, Pazos, Elena, Peinador, Carlos, García, Marcos D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.01.2022
Amer Chemical Soc
Subjects
Amino Acids
Chemistry
Chemistry, Organic
Macrocyclic Compounds
Peptides
Physical Sciences
Science & Technology
Viologens
RECOGNITION
ASSEMBLIES
CONSTRUCTION
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Summary: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.
Bibliography:European Research Council (ERC)
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02040