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Conformational behavior of α,α-dialkylated peptides

✍ Scribed by Vincenzo Barone; Francesco Lelj; Alfonso Bavoso; Benedetto Di Blasio; Patrizio Grimaldi; Vincenzo Pavone; Carlo Pedone

Publisher
Wiley (John Wiley & Sons)
Year
1985
Tongue
English
Weight
533 KB
Volume
24
Category
Article
ISSN
0006-3525

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✦ Synopsis

The preferred conformations of N-acetyl-"-methyl amides of some dialkylglycines have been determined by empirical conformational-energy calculations; minimum-energy conformations were located by minimizing the energy with respect to all the dihedral angles of the molecules. The conformational space of these compounds is sterically restricted, and lowenergy conformations are found only in the regions of fully extended and helical structures. Increasing the bulkiness of the substituents on the Ca, the fully extended conformation becomes gradually more stable than the helical structure preferred in the cases of dimethylglycine. This trend is, however, strongly dependent on the bond angles between the substituents on the C" atom: In particular, helical structures are favored by standard values (111") of the N-0-C' angle, while fully extended conformations are favored by smaller values of the same angle, as experimentally observed, for instance, in the case of a,a-di-n-propylglycine.

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