Amino Acids

, Volume 34, Issue 3, pp 465–471

Solid-phase peptide synthesis and circular dichroism study of chiral β-peptoid homooligomers

  • C. A. Olsen
  • M. Lambert
  • M. Witt
  • H. Franzyk
  • J. W. Jaroszewski
Article

DOI: 10.1007/s00726-007-0546-8

Cite this article as:
Olsen, C., Lambert, M., Witt, M. et al. Amino Acids (2008) 34: 465. doi:10.1007/s00726-007-0546-8

Summary.

N-alkyl-β-alanine oligomers (β-peptoids) with α-chiral side chains [(R)- or (S)-1-(phenylethyl)amino groups] were synthesized and analyzed by CD spectroscopy. These chiral β-peptoid homomers exhibited chain-length-dependent and solvent-dependent ellipticity, strongly indicating the presence of a secondary structure in solution. The CD behaviour was only slightly temperature-dependent upon heating, as also previously observed for stable α-peptoid helices containing the same type of side chains. Thus, the data presented here comprise the first evidence for a chain length-dependent secondary folding of compounds with this novel peptidomimetic backbone design. In addition, applicability of a novel hyphenated technique, HPLC-SPE-NMR/MS, for analysis of crude SPPS reaction products was demonstrated.

Keywords: Peptidomimetics – Chiral β-peptoids – Solid-phase synthesis – Circular dichroism – Secondary folding 

Abbreviations:

β-Nrpe

(R)-N-(1-phenylethyl)-β-alanine

β-Nspe

(S)-N-(1-phenylethyl)-β-alanine

CD

circular dichroism

DMF

N,N-dimethylformamide

HRMS

high-resolution mass spectrometry

MRE

mean residue ellipticity

PyBOP®

benzotriazol-1-yl-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate

RP-HPLC

reversed-phase high performance liquid chromatography

SPE

solid-phase extraction

SPPS

solid-phase peptide synthesis

TFA

trifluoroacetic acid

TFE

2,2,2-trifluoroethanol

TFFH

fluoro-N,N,N,N-tetramethylformamidinium hexafluorophosphate

Copyright information

© Springer-Verlag 2007

Authors and Affiliations

  • C. A. Olsen
    • 1
  • M. Lambert
    • 1
  • M. Witt
    • 2
  • H. Franzyk
    • 1
  • J. W. Jaroszewski
    • 1
  1. 1.Department of Medicinal Chemistry, Faculty of Pharmaceutical SciencesUniversity of CopenhagenCopenhagenDenmark
  2. 2.Bruker Daltonik GmbHBremenGermany

Personalised recommendations