Naphthomycin A

Naphthomycin A

Identifiers
ChemSpider	8276911
Jmol interactive 3D	Image
PubChem	10101379
SMILES O=C1c2c3C(=O)/C(=C1/Cl)NC(=O)/C(=C\C=C\C=C/[C@H](C)[C@@H](O)CC(=O)\C(=C/C[C@H](O)\C=C/[C@H](C)[C@H](O)[C@H](\C=C(\C(=O)c2c(O)c(c3)C)C)C)C)C
Properties
Chemical formula	C40H46ClNO9
Molar mass	720.26 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

Naphthomycin A is a type of naphthomycin. It was isolated as a yellow pigment from Streptomyces collinus and it shows antibacterial, antifungal, and antitumor activities.^[1] Naphthomycins have the longest ansa aliphatic carbon chain of the ansamycin family.^[2] Biosynthetic origins of the carbon skeleton from PKS1 were investigated by feeding 13C-labeled precursors and subsequent 13C-NMR product analysis. Naphthomycin gene clusters have been cloned and sequenced to confirm involvement in biosynthesis via deletion of a 7.2kb region.^[3] Thirty-two genes were identified in the 106kb cluster.^[4]

The proposed naphthomycin biosynthetic pathway.^[5] A, adenylation; KS, ketosynthase; AT, acyltransferase; T, acyl carrier protein or peptidyl carrier protein; DH, dehydratase; KR, ketoreductase; (*) redundant domain.

References

1. Kang, Q.; Y. Shenb; L. Bai (2012). "Biosynthesis of 3,5-AHBA-derived natural products". Nat. Prod. Rep. 29 (2): 243–263. doi:10.1039/c2np00019a. PMID 22193711.
2. Balerna, M.; W. Keller-Schierlein; C. Martius; H. Zahner (1969). "Stoffwechselprodukte von Mikroorganismen". Arch. Microbiol. 65 (4): 303–317. doi:10.1007/BF00412210. PMID 4988744.
3. Bai, L.; Y. Wu; Q. Kang; Y. Shen; Z. Deng (2012). Patent. CN: 2012-10300294: 225. Missing or empty |title= (help)
4. August, P.R.; L. Tang, Y.J. Yoon, S. Ning, R. MuEller, T.W. Yu, M. Taylor, D. Hoffman, C.G. Kim, X. Zahng, C.R. Hutchinson, H.G. Floss (1998). "Biosynthesis of the ansamycin antibiotic rifamycin: Deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699". Chem. Biol. 5 (2): 69–79. doi:10.1016/S1074-5521(98)90141-7. PMID 9512878. Cite uses deprecated parameter |coauthors= (help)
5. Kang, Q; Y. Shenb; L. Bai (2012). "Biosynthesis of 3,5-AHBA-derived natural products". Nat. Prod. Rep. 29 (2): 243–263. doi:10.1039/c2np00019a. PMID 22193711.