Tetrahedron p. 11281 - 11288 (1999)
Update date:2022-08-02
Topics:
Rueckle, Thomas
De Lavallaz, Pierre
Keller, Michael
Dumy, Pascal
Mutter, Manfred
Linear peptide H-Pro-Thr(Ψ(Me,Me)pro)-Pro-OH containing a preformed cis-Pro-Thr(Ψ(Me,Me)pro) tertiary amide bond cyclises instantaneously and free of formation of oligomeric structures to the cyclic tripeptide cyclo- [Pro-Thr(Ψ(Me,Me)pro)-Pro]. Even at concentrations up to 10-1 M peptide, no oligomeric structures are detected by mass spectroscopy and HPLC. 2D 1H NMR studies of purified cyclotripeptide reveal the compound to exist in one single conformation with all peptide bonds in the cis conformation. These results indicate enhanced cyclisation tendencies of cis-amide bond containing peptides of short chain length.
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