Representative LC/UV chromatogram under typical analytical conditions (C18 column; mobile phase: 5–100% ACN / H2O (0.05% H3PO4), linear gradient 20 min; flow rate: 0.2 mL/min; detection: 210 nm).
NMR Spectral Data
Representative 1H NMR (500 MHz) spectrum confirming the structure of Calpinactam. Representative 13C NMR (125 MHz) spectrum supporting structural assignment of Calpinactam.
Summary
Calpinactam is a fungal hexapeptide active against Mycobacterium species.
Details
Calpinactam is a fungal hexapeptide metabolite isolated from Mortierella alpina FKI-4905. Structurally, it contains a unique C-terminal caprolactam ring and was characterized by detailed NMR analysis and total synthesis. Calpinactam exhibits selective antimycobacterial activity, inhibiting the growth of Mycobacterium smegmatis and Mycobacterium tuberculosis with low-micromolar MIC values while showing minimal activity against other bacteria and fungi. Biosynthetic studies revealed that calpinactam is produced by a large nonribosomal peptide synthetase (NRPS), and heterologous expression systems have enabled its production from long fungal biosynthetic genes.