Tambjamine

It is hypothesized that tambjamines are a chemical defence mechanism of the bryozoan against feeding by the spotted kelpfish Gibbonsia elegans.

[3][4] The biosynthetic gene cluster responsible for tambjamine production was identified in 2007 using functional genomic analysis of a Pseudoalteromonas tunicata strain.

The biosynthesis of tambjamine YP1 first involves the incorporation of proline, malonyl Co-A, and serine to form 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde (MBC).

Condensation of the dodec-3-en-1-amine product of this reaction and MBC by TamQ, results in the tambjamine YP1 (compound 21 in Figure 1).

[7] It has subsequently been synthesised by other methods and used to make tambjamines and related natural products.

Figure 1: Chemical transformations and gene clusters for tambjamine biosynthetic pathways [ 5 ]