TY - JOUR
T1 - A Potent Cyclolinopeptide A Analogue
T2 - Solid State and Solution Conformation of cyclo[Pro-Phe-Phe-Ala-Glu(OtBu)]2
AU - Zanotti, Giancarlo
AU - Maione, Annamaria
AU - Rossi, Filomena
AU - Saviano, Michele
AU - Filizola, Marta
AU - Blasio, Benedetto Di
AU - Pedone, Carlo
AU - Tancredi, Teodorico
AU - Saviano, Gabriella
PY - 1995
Y1 - 1995
N2 - The conformational analysis of cyclo[Pro-Phe-Phe-Ala-Glu(OtBu)]2, in the solid state and in solution, has been carried out by X-ray diffraction and NMR spectroscopy. The structure of the orthorhombic form obtained from dioxane-water-acetonitrile mixture [a = 9,994(1) Å,b = 21.846(5) Å, c = 37.357(9) Å, space group P212121; Z = 4] shows the presence of four intramolecular NH–CO hydrogen bonds, with formation of two β turns (one of type I and one of type II) and two C14 ring structures. All peptide units are trans. The solution structure, as determined by NMR, indicates that, at room temperature, the peptide is conformationally homogeneous; the structure determined is perfectly symmetrical and topologically similar to that found in the solid state. The cyclodecapeptide exhibits similar biological activity to cyclolinopeptide A.
AB - The conformational analysis of cyclo[Pro-Phe-Phe-Ala-Glu(OtBu)]2, in the solid state and in solution, has been carried out by X-ray diffraction and NMR spectroscopy. The structure of the orthorhombic form obtained from dioxane-water-acetonitrile mixture [a = 9,994(1) Å,b = 21.846(5) Å, c = 37.357(9) Å, space group P212121; Z = 4] shows the presence of four intramolecular NH–CO hydrogen bonds, with formation of two β turns (one of type I and one of type II) and two C14 ring structures. All peptide units are trans. The solution structure, as determined by NMR, indicates that, at room temperature, the peptide is conformationally homogeneous; the structure determined is perfectly symmetrical and topologically similar to that found in the solid state. The cyclodecapeptide exhibits similar biological activity to cyclolinopeptide A.
UR - http://www.scopus.com/inward/record.url?scp=0029162856&partnerID=8YFLogxK
U2 - 10.1021/ja00138a022
DO - 10.1021/ja00138a022
M3 - Article
AN - SCOPUS:0029162856
SN - 0002-7863
VL - 117
SP - 8651
EP - 8658
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 33
ER -