Dehydroamino acids play a significant role in nature and in drug design. Up to the present however, few conformational studies have been carried out computationally on such molecules. The present study explored the stable conformations available to N-formyl-trans-2,3-didehydroalaninamide (trans- For-ΔAla-NH2). Seven minima (β(DL), δ(D), δ(L), ε(D), ε(L), γ(D) and γ(L)) were found at the B3LYP/6-31G* levels of theory, with the β(DL) conformer being the most stable. The ΔE(stabilization)((γ)<(SUBL)> indicated in the dehydroalanine residue is more stable than the glycine residue by -12.55 kcal/mol, although it is also more rigid. (C) 2000 Elsevier Science B.V.
- Ab initio study
- N- and C-protected trans-2,3-didehydroalanine
- α,β-dehydroamino acids
ASJC Scopus subject areas
- Condensed Matter Physics
- Physical and Theoretical Chemistry