Synthesis, resolution and assignment of absolute configuration of trans 3-amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic acid (POAC), a cyclic, spin-labelled beta-amino acid (Articolo in rivista)

Type

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

Label

• Synthesis, resolution and assignment of absolute configuration of trans 3-amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic acid (POAC), a cyclic, spin-labelled beta-amino acid (Articolo in rivista) (literal)

Anno

• 2008-01-01T00:00:00+01:00 (literal)

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

• 10.1016/j.tet.2008.02.058 (literal)

Alternative label

• Wright K., Dutot L., Wakselman M., Mazaleyrat J.P., Crisma M., Formaggio F., Toniolo C. (2008)
  Synthesis, resolution and assignment of absolute configuration of trans 3-amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic acid (POAC), a cyclic, spin-labelled beta-amino acid
  in Tetrahedron (Oxf., Print)
  (literal)

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

• Wright K., Dutot L., Wakselman M., Mazaleyrat J.P., Crisma M., Formaggio F., Toniolo C. (literal)

Pagina inizio

• 4416 (literal)

Pagina fine

• 4426 (literal)

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

• Citazioni WOS: 2 Impact Factor 2008: 2.897 Coautore (literal)

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

• 64 (literal)

Rivista

• Tetrahedron (Rivista)

Note

• ISI Web of Science (WOS) (literal)

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

• ILV, UMR CNRS 8180, University of Versailles, 78035 Versailles, France; Institute of Biomolecular Chemistry, Padova Unit, CNR, Department of Chemistry, University of Padova, 35131 Padova, Italy (literal)

Titolo

• Synthesis, resolution and assignment of absolute configuration of trans 3-amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic acid (POAC), a cyclic, spin-labelled beta-amino acid (literal)

Abstract

• Racemic trans 3-(9-fluorenylmethyloxycarbonylamino)-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic acid (Fmoc-POAC-OH), prepared by conventional methods, was resolved upon esterification with (aR)-2,2'-dihydroxy-1,1'-binaphthyl. Separation of the obtained diastereomeric monoesters Fmoc-(+/-)-trans-POAC-O-(aR)-binaphthol by crystallization/chromatography, and removal of the chiral auxiliary by saponification of the aryl ester function furnished both enantiomers (+)-(3R,4R)-Fmoc-POAC-OH and (-)-(3S,4S)-Fmoc-POAC-OH. The absolute configuration of the asymmetric C(3), C(4) carbons of POAC were assigned from the induced circular dichroism of a flexible biphenyl probe present in the terminally protected dipeptide derivatives Boc-Bip-(+)-POAC-OMe and Boc-Bip-(-)-POAC-OMe (Bip, 2',1':1,2;1 '',2 '':3,4-dibenzcyclohepta-1,3-diene-6-amino-6-carboxylic acid). This assignment was confirmed by X-ray diffraction analysis of the diastereomeric monoester Fmoc-(+)-trans-POAC-O-(aR)-binaphthol, shown to be (aR,3R,4R). Solution synthesis of peptides to the hexamer level, based on the (3RAR)-POAC enantiomer combined with (1S,2S)-2-aminocyclopentane-l-carboxylic acid, was carried out to examine coupling conditions at both C- and N-termini of the POAC residue, in view of further syntheses and 3D-structural investigations. (literal)

Prodotto di

• Peptidi antimicrobici e antivirali (PM.P01.013.001) (Modulo)
• Istituto di chimica biomolecolare (ICB) (Istituto)

Autore CNR

• MARCO CRISMA (Unità di personale interno)
• CLAUDIO TONIOLO (Persona)
• FERNANDO FORMAGGIO (Unità di personale esterno)

Incoming links:

Autore CNR di

• MARCO CRISMA (Unità di personale interno)
• CLAUDIO TONIOLO (Persona)
• FERNANDO FORMAGGIO (Unità di personale esterno)

Prodotto

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Peptidi antimicrobici e antivirali (PM.P01.013.001) (Modulo)

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

• Tetrahedron (Rivista)