Annimycin

Annimycin (4-(Z)-annimycin) is a polyenoic acid amide natural product produced by Streptomyces calvus.

[2] The ann2 gene encodes a 5-aminolevulinate synthase which condenses glycine and succinyl-CoA in a Claisen-like reaction to form 5-aminolevulinate.

The ann3 gene produces acyl-CoA ligase and is predicted to activate 5-aminolevulinate as the CoA thioester, which subsequently undergo intramolecular cyclization with a carbanion generated at C5 to form C5N.

The ann2 product is predicted to catalyze this cyclization using pyridoxal phosphate to stabilize the carbanion.

The gene ann1 encodes an ATP-dependent amide synthetase and is predicted to condense the amine of the C5N group with the polyenoic acid product forming annimycin.

Biosynthesis of annimycin proposed by Kalan et al ., [ 1 ] including the biosynthetic gene cluster and the encoded enzymes (Modification from original paper).