Undecylprodigiosin

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;
ChEBI	CHEBI:29702;
ChEMBL	ChEMBL83139 [EMBL];
ChemSpider	10481061 ;
PubChem CID	135515151;
UNII	ZQ2HK5E6ZG ;
	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−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[1]

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.^[2]

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.^[2]^[3]

Uses

As with other prodiginines, the compound has been investigated for its pharmaceutical potential as anticancer, immunosuppressant, or antimalarial agent.^[1]^[4]

References

^ ^a ^b 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.
^ ^a ^b 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.
^ 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.
^ 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.

[Williamson-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.

[Hu-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.

[pmid24562326-4] 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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