Conformational investigations on glycosylated threonine-oligopeptides of increasing chain length

Journal of Peptide Science : an Official Publication of the European Peptide Society
L BiondiR Rocchi

Abstract

Stepwise solution syntheses are described of the homo-oligomers Z-(Thr)n-NHCH3 (n=1-4, I1-4), Z-¿[Gal(Ac)4beta]Thr¿n-NHCH3(n=1-5, II1-5) and Z-[(Galbeta)Thr]n-NHCH3 (n=1-5, III1-5). Members of the III1-5 series were obtained by de-acetylation of the corresponding oligomers of the II1-5 series. The conformational preferences of the terminally protected homo-peptides of the three series were investigated by FT-IR absorption spectroscopy both in the solid state and in CDCl3 solution, at various concentrations. Proton NMR measurements in CDCl3 and in DMSO-d6 were also carried out and the effect of temperature variation on the chemical shifts of amide protons was determined in DMSO-d6 (range 298-335 K) and in CDCl3 (range 298-320K). CD spectra were recorded in water and in TFE. Solubility problems prevented measurements in CDCl3 solution for Z-(Thr)4-NHCH3 and for the entire III1-5 series. The existence of unordered structures in the carbohydrate-free oligomers and of more or less extended, organized structures in the glycosylated derivatives is indicated by the NMR and IR measurements. The sugar moieties apparently show a structure-inducing effect on the peptide chain.

References

Sep 14, 1977·Journal of the American Chemical Society·E S Pysh, C Toniolo
Jul 1, 1990·International Journal of Peptide and Protein Research·F FiliraR Rocchi
Jan 1, 1973·Biopolymers·A W Burgess, H A Scheraga
Jul 1, 1995·International Journal of Peptide and Protein Research·D V ReddyA C Kunwar
Feb 1, 1994·International Journal of Biological Macromolecules·C TonioloH E Schoemaker

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Citations

May 17, 2000·FEBS Letters·J G BannH P Bächinger
Jul 20, 2006·Chemistry : a European Journal·Francisco CorzanaA Avenoza
Dec 3, 1999·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·S HorvatL Varga-Defterdarović
Feb 28, 2002·Journal of Peptide Science : an Official Publication of the European Peptide Society·Laura BiondiRaniero Rocchi

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