Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: D-Alanine methylamide hydrochloride, is researched, Molecular C4H11ClN2O, CAS is 61302-99-6, about New Amino Acids for the Topographical Control of Peptide Conformation: Synthesis of All the Isomers of α,β-Dimethylphenylalanine and α,β-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid of High Optical Purity.Name: D-Alanine methylamide hydrochloride.
The synthesis of all four diastereoisomers of α,β-dimethylphenylalanine, H2NCMe(CHMePh)CO2H, (4) as well as those of α,β-dimethyl-1,2,3,4,-tetrahydroisoquinoline-3-carboxylic acid (I and II) have been accomplished in high yield and high optical purity. Mol. mechanics calculations on the Nα-acetyl and N-methylcarboxamide derivatives of (3R,4R)-I and (3R,4S)-II indicate large and moderate energy stabilization for the gauche(-) but not the gauche(+) side-chain conformers of (3R,4S)-II and (3R,4R)-I, resp. By symmetry rules, the same holds for (3S,4R)-II and (3S,4S)-I, resp. Thus, these amino acids are potential building blocks for the topog. design of peptides (W. M. Kazmierski et al., 1991) 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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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem