2022/02/23 by Yuko Bando, Yu Hou, Lydia Seyfarth +7 · 1 voice
Biochemistry, Genetics and Molecular Biology · #Insect Resistance and Genetics #Antibiotic Resistance in Bacteria #Beetle Biology and Toxicology Studies
paper · pdf · doi:10.1002/chem.202104417
openalex publication_date 2022/02/23 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01
Abstract A total synthesis of the cyclic lipodepsipeptide natural product orfamide A was achieved. By developing a synthesis format using an aminoacid ester building block and SPPS protocol adaptation, a focused library of target compounds was obtained, in high yield and purity. Spectral and LC‐HRMS data of all library members with the isolated natural product identified the 5 Leu residue to be d ‐ and the 3’‐OH group to be R ‐configured. The structural correction of orfamide A by chemical synthesis and analysis was confirmed by biological activity comparison in Chlamydomonas reinhardtii , which indicated compound configuration to be important for bioactivity. Acute toxicity was also found against Trypanosoma brucei , the parasite causing African sleeping sickness.