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- W2915367047 abstract "Systematic energy calculations were performed for a series of LHRH analogs including five agonists with substitutions of d ‐ or N ‐Me‐amino acid residues in positions 4, 6 and 7, and five antagonists with substitutions of d ‐, N ‐Me‐ or α‐Me‐amino acid residues in positions 1, 2, 3, 6, 7 and 10, as well as a bicyclic LHRH antagonist. The geometrical shapes of the calculated low‐energy backbone structures for each compound were compared to those of LHRH itself. It appeared that the β‐II′ turn at the Tyr 5 ‐Gly 6 ‐Leu 7 ‐Arg 8 central tetrapeptide is the common structure for all LHRH agonists considered. LHRH antagonists also possess a common chain reversal in the central tetrapeptide, but it is different from that for LHRH agonists. The LHRH agonists share a similar low‐energy conformer at the level of the entire peptide backbone. A characteristic feature of this conformer is a ‘surface’ formed by a ‘polygon’ with hydrophobic moieties of pGlu 1 , Trp 3 , Tyr 5 , Leu 7 and Pro 9 in the corners and with the side chain of the His 2 residue in the middle, the latter being crucial for a manifestation of LHRH agonistic activity. Since the N ‐terminal tripeptide of LHRH presumably participates in a direct interaction with specific receptors, it is legitimate to suggest that the β‐II′ turn in the central tetrapeptide maintains the proper spatial arrangement of the N ‐terminal tripeptide. On the other hand, LHRH antagonists considered in this study were shown to possess low‐energy structures, with the spatial arrangement of the residues in the N ‐terminal tripeptide similar to that of agonists. This would suggest a new approach to the design of LHRH antagonists, namely by stabilizing this specific arrangement, rather than the β‐II′ turn in the central tetrapeptide." @default.
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- W2915367047 date "1993-08-01" @default.
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- W2915367047 title "Conformation-function relationships in LHRH analogs" @default.
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- W2915367047 doi "https://doi.org/10.1111/j.1399-3011.1993.tb00495.x" @default.
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