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Peptide conformations 40. cyclic hexapeptide analogs of thymopoietin synthesis and conformational analysis



Peptide conformations 40. cyclic hexapeptide analogs of thymopoietin synthesis and conformational analysis



Liebigs Annalen der Chemie (5): 914-931



The syntheses of the four cyclic hexapeptides cyclo[-Arg(NO2)-Lys(Z)-Xxx(OBzl)-Val-Tyr-Gly-], c1: Xxx = Asp, c2: Xxx = Glu, cyclo[-Tyr-Val-Arg(NO2)-Lys(Z)-Xxx(OBzl)-D-Val-], c3: Xxx = Asp, c4: Xxx = Glu with thymopoietin-analogous sequences are described. The linear precursors of the cyclopeptides were synthesized by classical methods of peptide chemistry. Cyclization was carried out by the newly developed carbodiimide/DMAP method. The conformational studies of the four cyclohexapeptides gave different results. The NMR data of the glycine-containing cyclopeptides c1 and c2 correlate with an equilibrium of different conformations, whereas the D- and L-valine-containing cyclohexapeptides c3 and c4 are conformationally homogenous. The conformational analysis proves that these cyclohexapeptides adopt a .beta.II'.beta.I'-structure.

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