Amino Acids

, Volume 41, Issue 3, pp 629–641 | Cite as

Chiral, fully extended helical peptides

  • Marco Crisma
  • Alessandro Moretto
  • Cristina Peggion
  • Lavinia Panella
  • Bernard Kaptein
  • Quirinus B. Broxterman
  • Fernando Formaggio
  • Claudio Toniolo
Original Article
First Online:
Received:
Accepted:

Abstract

The synthesis of the N-protected (blocked) homo-peptide esters from the chiral Cα-ethyl, Cα-n-pentylglycine was performed in solution to the hexapeptide level. The conformational propensity exhibited by these oligomers in chloroform solution and in the crystal state was assessed by use of FTIR absorption, NMR, and X-ray diffraction. The results indicated that fully extended helical structures (2.05-helices) are overwhelmingly adopted irrespective of the peptide main-chain length. This oligomeric series is of great interest as it is characterized by the longest C i α ,…, C i+1 α (per residue) separation achievable in the class of chiral, rigid, helical peptide spacers based on α-amino acids.

Keywords

Fully extended helix Homo-oligopeptides Infrared absorption Nuclear magnetic resonance Cα-Tetrasubstituted α-amino acids X-ray diffraction 

Abbreviations

Ac

Acetyl

Acnc

1-Aminocycloalkane-1-carboxylic acid

Aib

α-Aminoisobutyric acid or Cα-methylalanine or Cα,α-dimethylglycine

(αMe)AA

Cα-Methylated α-amino acid

Beg

Cα-n-Butyl, Cα- ethylglycine

Deg

Cα,α-Diethylglycine

DMAP

4-(dimethylamino)Pyridine

DMSO

Dimethylsulphoxide

Dpg

Cα,α-di-n-Propylglycine

EDC

N-Ethyl,N′-[3-(dimethylamino)propyl]carbodiimide

Epg

Cα-Ethyl, Cα-n-pentylglycine

Etn

Cα-Ethylnorvaline or Cα-ethyl, Cα-n-propylglycine

EtOH

Ethanol

Iva

Isovaline or Cα-methyl, Cα-ethylglycine

MeOH

Methanol

MTBE

Methyl, tert-butyl ether

OMe

Methoxy

OSu

Succinimido

OtBu

tert-Butoxy

TEMPO

2,2,6,6-Tetramethylpiperidinyl-1-oxy

Tfa

Trifluoroacetyl

Z

Benzyloxycarbonyl

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Notes

Acknowledgments

A.M. and F.F. are grateful to the University of Padova for financial support through the PRAT 2007 funding initiative.

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Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Marco Crisma
    • 1
  • Alessandro Moretto
    • 1
  • Cristina Peggion
    • 1
  • Lavinia Panella
    • 2
  • Bernard Kaptein
    • 2
  • Quirinus B. Broxterman
    • 2
  • Fernando Formaggio
    • 1
  • Claudio Toniolo
    • 1
  1. 1.ICB, Padova Unit, CNR, Department of ChemistryUniversity of PadovaPaduaItaly
  2. 2.DSM Innovative Synthesis BVGeleenThe Netherlands

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