INVESTIGATION OF THE PEPTIDE BACKBONE FOLDINGS. SYNTHESIS AND CONFORMATIONAL ANALYSIS OF ANALOGUES OF THE CENTRAL SEQUENCE OF ANGIOTENSIN II. UV-VIS AND NMR SPECTROSCOPIES
Abstract
SPECIFIC SIDE CHAIN-SIDE CHAIN INTERACTIONS BETWEEN TRP AND NVA(NIC+) HAVE BEENSUCCESSFULLY VISUALIZED BY APPLYING CHARGE TRANSFER MARKERS IN THE LRF MOLECULE (P-GLU-HIS-TRP-SER-TYR-GLY- LEU-ARG-PRO-GLY-NH2) AND ANALOGUES OF ITS CENTRALSEQUENCE, ACCORDING TO THE PROBABILITY OF B-TURN FORMATION. ON THE OTHER HAND,SIDE CHAIN-SIDE CHAIN INTERACITONS BETWEEN TYR4 AND HIS6 IN ANGIOTENSIN II, ASP-ARG-VAL-TYR-VAL-HIS-PRO- PHE, HAVE BEEN STUDIED BY THE COMBINED USE OF C.D., I.R. AND NMR EXPERIMENTS. WITH THE AIM OF FORMULATING A RATHER SIMPLE WAY TO EVALUATE LONG DISTANCE INTERACTIONS OF THIS KIND IN PEPTIDES WITH MORE OR LESS EXTENDED BACKBONE CONFORMATIONS WE HAVE SYNTHESIZED THE FOLLOWING SERIES OF TRIPEPTIDES: AC-TRP-X-NVA(NIC+)-NH2,CL- WHERE X=VAL, LEU, ALA, GLY. ALL THE FOUR ANALOGUES SHOWED A CHARACTERISTIC CHARGE TRANSFER BAND AND THE DIFFERENCES IN THE INTENSITY REVEALED AN INCREASED SIDE CHAIN-SIDE CHAIN INTERACTION IN THE ORDER OF GLY<ALA<LEU<VAL, I.E. AS THE FOLDING OF THE BACKBONE ...
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