Conformation of Actinomycin-D

  title={Conformation of Actinomycin-D},
  author={F. Conti and P. Santis},
NUCLEAR magnetic resonance (NMR) spectroscopy has recently been found useful for investigating the conformations of polypeptides like gramicidin S1,2, valinomicin3 and so on. We now report preliminary conclusions on the conformation of the two peptide lactone rings of actinomycin D4 on the basis of NMR results and theoretical conformational analysis. Fig. 1 depicts the NMR spectra of actinomycin D obtained in different experimental conditions. The assignment has been made on the basis of… Expand
25 Citations
NMR study of the solution conformation of actinomycin D.
  • C. Yu, Y. Tseng
  • Chemistry, Medicine
  • European journal of biochemistry
  • 1992
The solution conformation of actinomycin D, the Gram-positive antibiotic and DNA-binding drug, has been determined by 1H-NMR in deuterated dimethyl sulfoxide by finding these structures to be compatible with the X-ray crystal structures. Expand
NMR studies of viomycin
The 1H and 13C NMR spectra of antibiotic Viomycin sulphate and its constituent aminoacids in H2O and D2O were examined in a wide range of pH values. The spectra were analysed by proton spin-spinExpand
Proton magnetic resonance studies of actinomycin‐related peptides containing N‐methyl groups
The PMR spectra of several cyclic and acyclic dipeptide derivatives representing portions of the actinomycin structure have been studied. In the spectra of the acyclic compounds temperature-dependentExpand
Actinomycin D, 1H NMR studies on intramolecular interactions and on the planarity of the chromophore.
At lower temperatures a simultaneous and selective broadening of the alpha ring threonine and valine amide proton signals as well as of the 2-amino group resonance was observed, indicating the presence of one dynamic process in the molecule which slows down upon temperature reduction. Expand
Intramolecular interactions, mesomerism and dynamics in actinomycin D studied by 15N NMR spectroscopy.
Evidence is presented that the pentapeptide rings of actinomycin D have different conformations in polar and in apolar solvents, and the chromophoric N10 is efficiently solvent-protected, the solvent-dependence of its 15N resonance resulting from solvent interactions at other positions of the molecule and from solvent-dependent changes in the twisting of the Chromophoric system. Expand
NMR studies of actinomycins varying at the proline sites
The proton NMR spectra of 14 actinomycins and the 13C NMR data for four of these compounds were compared with those of actinomycin D. These compounds differ from actinmycin D by the replacement ofExpand
Biosynthesis and characterization of [15N]actinomycin D and conformational analysis by nitrogen-15 nuclear magnetic resonance.
A model for the solution conformation of the actinomycin pentapeptide rings based on different hydrogen-bonding interactions in the monomer in organic solvents and the dimer which is formed in water is discussed. Expand
High-resolution proton nuclear magnetic resonance analysis of conformational properties of biosynthetic actinomycin analogues.
Examination of the low-field position of the H alpha proton of the 3'-amino acid reveals that the biosynthetic substitutions were made at a unique site on either the alpha or the beta pentapeptide ring and that only one conformation of proline, azetidine-2-carboxylic acid, or pipecolic acid is observed. Expand
Role of actinomycin pentapeptides in actinomycin-deoxyribonucleic acid binding and kinetics.
The strongest DNA binding analog, in terms of the largest binding constant, the largest increase in DNA thermal denaturation temperature, and the slowest DNA dissociation rate, was actinomycin V, which has 4-ketoproline in the beta peptide ring, while the weakest DNA binding analogue has pipecolic acid on both peptide rings. Expand
The stereochemistry of actinomycin binding to DNA and its implications in molecular biology.
  • H. M. Sobell
  • Biology, Medicine
  • Progress in nucleic acid research and molecular biology
  • 1973
The successful cocrystallization of actinomycin with its DNA substrate, deoxyguanosine, and thus, have solved the three-dimensional structure of the complex by X-ray crystallography, demonstrating a general symmetry principle that several classes of proteins may utilize in recognizing symmetrically arranged nucleotide sequences on the DNA helix. Expand


Nuclear Magnetic Resonance Study of the Structure and Interactions of Actinomycin D: Temperature and Solvent Effects on the N—H and NH2 Groups  
The assignment and the effects of solvent and temperature on the N—H, NH2 and actinocin ring proton signals in ACD are reported. Expand
220 Mc Nuclear Magnetic Resonance Spectra of Gramicidin S in Solution
The nuclear magnetic resonance spectra at 100 Mc of gramicidin S in dimethylsulphoxide (DMSO) solution and a preliminary tentative assignment of the resonance peaks show that the peak at 9.1 p.p.m., which had been attributed to an impurity, corresponds to the NH protons of phenylalanine residues. Expand
Conformational studies of peptide systems. The rotational states of the NH--CH fragment of alanine dipeptides by nuclear magnetic resonance.
The conformation of the 7-membered hydrogen-bonded ring of the dipeptides has been elucidated and an empirically found stereochemical dependence of the constant 3 J NHCH upon the dihedral angle θ of the fragment has served as basis for discussing the possible conformations of the extended form of the Dipeptide molecules in polar solvents. Expand
Actinomycine, XXXII. Oxydative Abspaltung des β‐Pentapeptidlactonringes aus Actinomycin C2 und C3; ein Beweis für die Bis‐pentapeptidacton‐Struktur der Actinomycine
Oxydation von 2-Desamino-2-hydroxy-actinomycin C3 und C2 (1c und 1d) liefert N-Oxal-cyclo-[L-Thr-D-aIle-L-Pro-Sar-L-MeVal-OThr] (3a); ein Beweis, das die zehn Aminosauren von Actinomycin C3 und C2 zuExpand
Conformational aspects of polypeptide structure. XX. Helical poly-N-methyl-L-alanine. Experimental results.
[On the behavior of actinomycins in aqueous solutions].
  • W. Müller, I. Emme
  • Chemistry, Medicine
  • Zeitschrift fur Naturforschung. Teil B, Chemie, Biochemie, Biophysik, Biologie und verwandte Gebiete
  • 1965