Publication

Org. Lett. 23, 2616-2620 (2021)
Biosynthesis of cyclochlorotine: Identification of the genes involved in oxidative transformations and intramolecular O,N-transacylation

Author

Jiang, Y.; Ozaki, T.*; Liu, C.; Igarashi, Y.; Ye, Y.; Tang, S.; Ye, T.; Maruyama, J.; Minami, A.*; Oikawa, H.*

Category

Article

Mycotoxin cyclochlorotine (1) and structurally related astins are cyclic pentapeptides containing unique nonproteinogenic amino acids, such as β-phenylalanine, l-allo-threonine, and 3,4-dichloroproline. Herein, we report the biosynthetic pathway for 1, which involves intriguing tailoring processes mediated by DUF3328 proteins, including stereo- and regiospecific chlorination and hydroxylation and intramolecular O,N-transacylation. Our findings demonstrate that DUF3328 proteins, which are known to be involved in oxidative cyclization of fungal ribosomal peptides, have much higher functional diversity than previously expected.