Journal of the American Chemical Society p. 7154 - 7163 (1985)
Update date:2022-08-02
Topics: Nuclear magnetic resonance (NMR) spectroscopy Conformation Dimerization X-ray crystallography Solid State Experimental Dimer Solution
Mauger, Anthony B.
Stuart, Oswald A.
Ferretti, James A.
Silverton, James V.
Actinomycin-related peptide lactone derivatives with the amino acid sequences Thr-D-Val-Pro-Sar-MeVal and Thr-D-Val-Pro-Sar-MeAla and the corresponding actinomycins (actinomycin D and its novel 5,5'-MeAla analoque) were synthesized by a new route.The solution properties of these compounds were studied by proton NMR in chloroform and acetone solutions.In dry chloroform, two conformers, A and C, are found, the ratio of which was concentration-dependent and results from dimerization of the A conformer.An X-ray crystallographic investigation of a Thr-D-Val-Pro-Sar-MeAla derivative indicated that hydrogen-bond associated pairs of A conformers, with a juxtapositional geometry remarkably similar to that known for actinomycin, were present in the solid state.
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