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.
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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
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Authors’ address: Dr. C. A. Olsen, Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark; Present address: The Scripps Research Institute
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Olsen, C., Lambert, M., Witt, M. et al. Solid-phase peptide synthesis and circular dichroism study of chiral β-peptoid homooligomers. Amino Acids 34, 465–471 (2008). https://doi.org/10.1007/s00726-007-0546-8
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DOI: https://doi.org/10.1007/s00726-007-0546-8