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Undecylprodigiosin

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Undecylprodigiosin
Names
IUPAC name (2Z,5Z)-3-Methoxy-5-pyrrol-2-ylidene-2-pyrrole
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
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/h12,14-19,26-27H,3-11,13H2,1-2H3/b24-18-Key: HIYSWASSDOXZLC-MOHJPFBDSA-N
SMILES
  • CCCCCCCCCCCC1=CC=C(N1)/C=C\2/C(=CC(=N2)C3=CC=CN3)OC
Properties
Chemical formula C25H35N3O
Molar mass 393.575 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Undecylprodigiosin is an alkaloid produced by some Actinomycetes bacteria. It is a member of the prodiginines group of natural products and has been investigated for potential antimalarial activity.

Natural sources

Undecylprodigiosin is a secondary metabolite found in some Actinomycetes, for example Actinomadura madurae, Streptomyces coelicolor and Streptomyces longisporus.

Production

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.

Biosynthesis of undecylprodigiosin

Laboratory

The first total synthesis of the undecylprodigiosin was published in 1966, confirming the chemical structure. As with the biosynthesis, the key intermediate was MBC.

Uses

As with other prodiginines, the compound has been investigated for its pharmaceutical potential as anticancer, immunosuppressant, or antimalarial agent.

References

  1. ^ Williamson NR, Fineran PC, Gristwood T, Leeper FJ, Salmond GP (2006). "The biosynthesis and regulation of bacterial prodiginines". Nature Reviews Microbiology. 4 (12): 887–899. doi:10.1038/nrmicro1531. PMID 17109029. S2CID 11649828.
  2. ^ 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.
  3. Wasserman, H. H.; Rodgers, G. C.; Keith, D. D. (1966). "The structure and synthesis of undecylprodigiosin. A prodigiosin analogue from Streptomyces". Chemical Communications (22): 825–826. doi:10.1039/C19660000825.
  4. Stankovic, Nada; Senerovic, Lidija; Ilic-Tomic, Tatjana; Vasiljevic, Branka; Nikodinovic-Runic, Jasmina (2014). "Properties and applications of undecylprodigiosin and other bacterial prodigiosins". Applied Microbiology and Biotechnology. 98 (9): 3841–3858. doi:10.1007/s00253-014-5590-1. PMID 24562326. S2CID 16834175.
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