Undecylprodigiosin

Undecylprodigiosin is an alkaloid produced by Streptomyces bacteria. It is one of the prodiginines pigments that is used for different medical uses including antimalarial activity.

Undecylprodigiosin

Names
IUPAC name (2Z,5Z)-3-Methoxy-5-pyrrol-2-ylidene-2-[(5-undecyl-1H-pyrrol-2-yl)methylidene]pyrrole
Identifiers
CAS Number	52340-48-4
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL83139
ChemSpider	10481061
PubChem CID	6438379
InChI InChI=1S/C25H35N3O/c1-3-4-5-6-7-8-9-10-11-13-20-15-16-21(27-20)18-24-25(29-2)19-23(28-24)22-14-12-17-26-22/h12,14-19,27-28H,3-11,13H2,1-2H3/b23-22-,24-18- Key: ISFCPXILUVJVOC-KYGJEJSHSA-N
SMILES CCCCCCCCCCCC1=CC=C(N1)C=C2C(=CC(=C3C=CC=N3)N2)OC
Properties
Chemical formula	C25H35N3O
Molar mass	393.575 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Biosynthesis

The biosynthesis of undecylprodigiosin starts with PCP apoprotein which is transformed into the holoprotein using acetyl CoA and PPtase then adenylation occurs utilizing L-proline and ATP. The resulting molecule is then oxidized by dehydrogenase enzyme. Elongation by decarboxylative condensation with malonyl CoA is followed by another decarboxylative condensation with L-serine using α-oxamine synthase (OAS) domain. The compound is then cyclized, oxidized with dehydrogenase and methylated with SAM to give 4-Methoxy-2,2′-bipyrrole-5-carboxaldehyde (MBC) intermediate which react with 2-undecylpyrrole (2-UP) to give undecylprodigiosin.[1]

Biosynthesis of undecylprodigiosin

References

1. Hu, Dennis X.; Withall, David M.; Challis, Gregory L.; Thomson, Regan J. (17 June 2016). "Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products". Chemical Reviews. 116 (14): 7818–7853. doi:10.1021/acs.chemrev.6b00024. PMC 5555159. PMID 27314508.