Tetrahedron p. 10883 - 10900 (1995)
Update date:2022-08-03
Topics:
Obrecht, Daniel
Bohdal, Udo
Daly, John
Lehmann, Christian
Schoenholzer, Peter
Mueller, Klaus
A novel and efficient synthesis of optically pure (R)- and (S)-α-methyl glutamic acid (1), (R)-and (S)-α-methyl aspartic acid (2a) and (R)- and (S)-α-isobutyl aspartic acid (2b) using L-phenylalanine cyclohexylamide 4 as chiral auxiliary is described.Crystal structures show that the (R)- and (S)-α-methyl glutamic acid derivatives (S,S)-5 and (R,S)-6 adopt β-turn type I geometries, whereas the corresponding aspartimide derivatives (R,S)-12a,b form a β-turn type II and (S,S)-11a a β-turn type II'.These findings suggest, that the succinimide derivatives of (R)- and (S)-α-alkyl aspartic acids can serve as building blocks to stabilise β-turns of type II (or II') in peptides depending on their absolute configuration.
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