Journal of Organic Chemistry p. 1789 - 1795 (1994)
Update date:2022-07-30
Topics:
Kazmierski, Wieslaw M.
Urbanczyk-Lipkowska, Zofia
Hruby, Victor J.
The synthesis of all four diastereomers of α,β-dimethylphenylalanine (4) as well as those of α,β-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (5 and 6) have been accomplished in high yield and high optical purity.Molecular mechanics calculations on the Nα-acetyl and N-methylcarboxamide derivatives of (3R,4R)-6 and (3R,4S)-5 indicate large and moderate energy stabilization for the gauche(-) but not the gauche(+) side-chain conformers of (3R,4S)-5 and (3R,4R)-6, respectively.By symmetry rules, the same holds for (3S,4R)-5 and (3S,4S)-6, respectively.Thus, these amino acids are potential building blocks for the topographical design of peptides (Kazmierski et al., J.Am.Chem.Soc. 1991, 113, 2275-2283) by providing acylated 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives in which a gauche(-) and not a gauche(+) side-chain conformation is energetically more stable for the L amino acid.Synthetic details and implications of these new amino acids for peptide and protein design are discussed.
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