Synthesis and Conformational Study of Model Peptides Containing N-Substituted 3-Aminoazetidine-3-carboxylic Acids (Articolo in rivista)

Type

• Prodotto della ricerca (Classe)
• Articolo in rivista (Classe)

Label

• Synthesis and Conformational Study of Model Peptides Containing N-Substituted 3-Aminoazetidine-3-carboxylic Acids (Articolo in rivista) (literal)

Anno

• 2014-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1002/ejoc.201301741 (literal)

Alternative label

• Zukauskaite, Asta; Moretto, Alessandro; Peggion, Cristina; De Zotti, Marta; Sackus, Algirdas; Formaggio, Fernando; De Kimpe, Norbert; Mangelinckx, Sven (2014)
  Synthesis and Conformational Study of Model Peptides Containing N-Substituted 3-Aminoazetidine-3-carboxylic Acids
  in European journal of organic chemistry (Print)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Zukauskaite, Asta; Moretto, Alessandro; Peggion, Cristina; De Zotti, Marta; Sackus, Algirdas; Formaggio, Fernando; De Kimpe, Norbert; Mangelinckx, Sven (literal)

Pagina inizio

• 2312 (literal)

Pagina fine

• 2321 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 2014 (literal)

Rivista

• European journal of organic chemistry (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

• 10 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

• 11 (literal)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium; Institute of Synthetic Chemistry, Kaunas University of Technology, Radvilenu pl. 19, 50270 Kaunas, Lithuania; Institute of Biomolecular Chemistry, CNR, Padova Unit, Department of Chemistry, University of Padova, Via Marzolo 1, 35131 Padova, Italy (literal)

Titolo

• Synthesis and Conformational Study of Model Peptides Containing N-Substituted 3-Aminoazetidine-3-carboxylic Acids (literal)

Abstract

• Model peptides containing N-substituted 3-aminoazetidine-3-carboxylic acids have been synthesized to investigate the conformational features of these C-tetrasubstituted amino acids. The target peptides were designed and prepared by classical synthetic methods in solution, exploiting the convenient N-substituted 3-azidoazetidine-3-carboxylic acids as precursors. The conformational preferences of the newly synthesized peptides were investigated in solution by IR and NMR spectroscopy. It was observed that the 3-aminoazetidine-3-carboxylic acid moiety is likely a -turn inducer. In addition, an interesting main-chain-to-side-chain hydrogen bond that forms a six-membered pseudo-cycle was detected. It connects the nitrogen (acceptor) of the azetidine ring to the amide NH (donor) of the immediately following residue. This unexpected hydrogen bond increases the number of conformational options offered by N-substituted 3-aminoazetidine-3-carboxylic acids when designing foldamers with new and predictable 3D structures. (literal)

Prodotto di

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Peptidi da amminoacidi non proteici con potenzialità in nanomedicina (PM.P01.021.001) (Modulo)

Autore CNR

• FERNANDO FORMAGGIO (Unità di personale esterno)
• ALESSANDRO MORETTO (Persona)

Insieme di parole chiave

• Parole chiave di "Synthesis and Conformational Study of Model Peptides Containing N-Substituted 3-Aminoazetidine-3-carboxylic Acids" (Insieme di parole chiave)

Incoming links:

Prodotto

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Peptidi da amminoacidi non proteici con potenzialità in nanomedicina (PM.P01.021.001) (Modulo)

Autore CNR di

• ALESSANDRO MORETTO (Persona)
• FERNANDO FORMAGGIO (Unità di personale esterno)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• European journal of organic chemistry (Rivista)

Insieme di parole chiave di

• Parole chiave di "Synthesis and Conformational Study of Model Peptides Containing N-Substituted 3-Aminoazetidine-3-carboxylic Acids" (Insieme di parole chiave)