Chondromyces crocatus Chondramides

Proteobacteria, Myxobacteria Chondromyces crocatus (chondramides A—D) [90]. F Basidiomycota Cortinarius violaceusa [5]. P Acanthaceae Aphelandra spp. (aphel-andrine, orantine [102]) Veronicaceae Chaenorhinum sp. [(S)-/ -Tyr chaenorhine, chaenorpine] [103]. 

Kunze B, Jansen R, Sasse F, Hofle G, Reichenbach (1995) Chondramides A-D, New Antifungal and Cytostatic Depsipeptides from Chondromyces crocatus (Myxobacteria). Production, Physico-Chemical and Biological Properties. J Antibiot 48 1262... 

Figure 14 Biosynthesis of PKS-NRPS hybrid compounds in myxobacteria (b). Biosynthesis of chondramide D (34) in Chondromyces crocatus Cm c5. The DH domain from module 1 (marked with an asterisk) is most likely inactive. During the assembly of the chondramide backbone, an unusual extender unit - a /3-amino acid - is incorporated by NRPS module 6. The precursor is generated by the tyrosine amino mutase (TAM) CmdF, which converts L-tyrosine into R-/3-tyrosine (see box). The function of the terminal phosphoenolpyruvate synthase (PEP) domain is still unknown. Macrocyclization catalyzed by the TE domain yields chondramide C (40), which can be further transformed to the chlorinated derivative chondramide D (34). The halogenation process catalyzed by CmdE may also take place on the assembly line intermediate.

Kunze, B., Jansen, R., Reichenbach, H., and Hofle, G. (1996) Chondramides A-D, new cytostatic and antifungal cyclodepsipeptides from Chondromyces crocatus (myxobacteria) Isolation and structure elucidation. Liebigs Ann. Chem., 1996 (2), 285-290. 

Rachid S, Krug D, Kunze B, Kochems I, Scharfe M, Zabriskie TM, Blocker H, Mueller R. Molecular and biochemical studies of chondramide formation-highly cytotoxic natural products from Chondromyces crocatus cm c5. Chem. Biol. 2006 13 667-681. 

---