Dehydrooligopeptides. X. Useful Synthetic Method for (<i>E</i>)- and (<i>Z</i>)-Isomers of Dehydroaspartic Acids, and Their<i>Δ</i><sup>1,2</sup>-Dehydrodipeptides by the Base-Catalyzed β-Elimination
derivatives were successfully synthesized by both a base-catalyzedβ-elimination of β-hydroxyaspartic acid esters (HyAsp) via their β-mesyloxy Asp derivatives and several modes of the cleavages of α-(N-Cbz)-aminomaleic acid anhydride. Moreover, for high-yield synthesis of Δ1,2-dehydrodipeptides (DHP) containing a ΔAsp residue, a similar β-elimination was applied to Δ1-DHP with a C-terminal HyAsp residue
Synthesis and antimicrobial studies of cadasides analogues via on-resin esterification
作者:Xiangzhen Yan、Chengshuo He、Zhuang Li、Kang Jin
DOI:10.1016/j.bmc.2024.117601
日期:2024.2
have been prepared via a combination of solid-phase peptide synthesis and solution-phase cyclization. Primary structure-activityrelationship studies of cadasides have also been established and revealed the critical roles of unnatural amino acid residues, which will facilitate the further development of cadasides analogues with improved antimicrobial activities.
The gamma-azetidinyl-beta-hydroxy-alpha-amino acid derivative 2, a key intermediate for the total synthesis of mugineic acid (1), was stereoselectively prepared from readily available (2R,3R)-epoxysuccinic acid (3).