Letters in Peptide Science

, Volume 7, Issue 2, pp 123–131 | Cite as

Afc can adopt either the fully extended or a turn conformation

  • Marco Crisma
  • Fernando Formaggio
  • Stefano Mezzato
  • Claudio Toniolo
  • Jaroslav Savrda
  • Jean-Paul Mazaleyrat
  • Michel Wakselman
Article
  • 31 Downloads

Summary

We have synthesized by solution methods and fully characterized two sets of terminally protected peptides based on the tricyclic Cα,α-disubstituted glycine Afc. The conformational preferences of the Afc/Gly peptides were examined by FT-IR absorption and1H NMR techniques, while those of the Afc/TOAC peptides were primarily investigated by using fluorescence spectroscopy. The X-ray diffraction structure of an Afc derivative was also analyzed. The body of solution and crystal-state experimental data conclusively confirms previous findings that the Afc residue may either adopt the fully extended (C5) or a turn conformation.

Key words

9-amino-9-fluorenecarboxylic acid conformational analysis fluorescence peptide synthesis X-ray diffraction 

Abbreviations

Ac5c

1-aminocyclopentane-1-carboxylic acid

Afc

9-amino-9-fluorenecarboxylic acid

Aib

α-aminoisobutyric acid

(αMe)Val

Cα-methyl valine

Boc

tert-butyloxycarbonyl

Bz

benzoyl

DMSO

dimethylsulfoxide

DΦg

Cα,α-diphenylglycine

EDC

N-ethyl, N′-(3-dimethylaminopropyl)-carbodiimide

EEDQ

1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

HOAt

7-aza-1-hydroxy-1,2,3-benzotriazole

NHtBu

tert-butylamin

OMe

methoxy

TEMPO

2,2,6,6-tetramethylpiperidinyl-1-oxy

TOAC

2,2,6,6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid

Z

benzyloxycarbonyl

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Copyright information

© Kluwer Academic Publishers 2000

Authors and Affiliations

  • Marco Crisma
    • 1
  • Fernando Formaggio
    • 1
  • Stefano Mezzato
    • 1
  • Claudio Toniolo
    • 1
  • Jaroslav Savrda
    • 2
  • Jean-Paul Mazaleyrat
    • 2
  • Michel Wakselman
    • 2
  1. 1.Biopolymer Research Center, CNR, Department of Organic ChemistryUniversity of PadovaPadovaItaly
  2. 2.SIRCOBUniversity of VersaillesVersaillesFrance

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