Insight into the structure of antitubercular Callyaerins: conformational studies and synthesis of a unique dehydroamino acid, β-aminodehydroalanine.

ABSTRACT: β-Aminodehydroalanine, ΔAla(β-NH), (2,3-diaminoprop-2-enoic acid), is a unique dehydroamino acid and a central component of Callyaerins A-M and Callynormine A. The presence of this unusual structural element containing an enamine functional group may be related to the antitubercular activity of Callyaerins. According to The WHO Global Tuberculosis Report tuberculosis is the second leading cause of death worldwide caused by a single infectious agent. Therefore, it is essential to understand the molecular structure of these peptides in more detail. To investigate the conformational properties of the ΔAla(β-NH) residue, a series of model compounds: Ac-(Z/E)-ΔAla(β-NHMe)-NHMe, Ac-(Z/E)-ΔAla(β-NHMe)-NMe₂, Boc-Gly-(Z)-ΔAla(β-NHMe)-OMe, and Boc-Gly-(Z)-ΔAla(β-Leu-OMe)-OMe, were selecte

SUBMITTER: Banas K 

PROVIDER: S-EPMC12360971 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature