| 초록 |
There is ever-growing interest in the synthesis and biological evaluation of non-proteinogenic amino acids, peptides and peptidomimetics. We developed a convenient synthetic access to all four diastereomers of 3-mercaptoaspartic acid derivatives from L-aspartic acid. The key intermediates, trans-(4S,5S)- and cis-(4S,5R)-oxazolines were ring-opened with thiolacetic acid to afford the desired L-erythro- and L-threo-3-mercaptoaspartic acids with a clean inversion of configuration at the C-5 position of the parent oxazolines, respectively. The other two D-stereoisomers were also synthesized using the stereochemical interconversion of α- and β-configuration as key steps. |
