Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Chemical Compound Review:

C11998 (2R,3R,7R,9S,10S,11R,13R)-10- [(2S,3R,4S...

Synonyms:

Sherman, D.H. et al., Xue, Y. et al., Xue, Y. et al., Butler, A.R. et al., Ikeda, H. et al., et al.

Sherman, Li, Yermalitskaya, Kim, Smith, Waterman, Podust,

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Disease relevance of C11998

Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae [1].

High impact information on C11998

The antibacterial properties of macrolide antibiotics (such as erythromycin, tylosin, and narbomycin) depend ultimately on the glycosylation of otherwise inactive polyketide lactones [2].
The results provide important new insights into the structural basis for the C10/C12 and C12/C14 hydroxylation patterns for the 12-(YC-17) and 14-membered ring (narbomycin) macrolides, respectively [3].
Purified PikC effectively converts YC-17 into methymycin and neomethymycin and narbomycin into pikromycin in vitro [1].
Characterization of the macrolide P-450 hydroxylase from Streptomyces venezuelae which converts narbomycin to picromycin [4].
The methymycin and pikromycin series of antibiotics are structurally related macrolides produced by several Streptomyces species, including Streptomyces venezuelae ATCC 15439, which produces both 12-membered ring macrolides methymycin, neomethymycin, and 14-membered ring macrolides pikromycin and narbomycin [5].

Biological context of C11998

One of the prototrophic fusants produced narbomycin, which is believed to be due to a result of interspecific recombination [6].

Analytical, diagnostic and therapeutic context of C11998

Functional significance of the salt bridge was corroborated by site-directed mutagenesis that revealed a key role for Glu-94 in YC-17 binding and Glu-85 for narbomycin binding [3].

References

Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae. Xue, Y., Wilson, D., Zhao, L., Liu, H., Sherman, D.H. Chem. Biol. (1998) [Pubmed]
Genetic engineering of aminodeoxyhexose biosynthesis in Streptomyces fradiae. Butler, A.R., Bate, N., Kiehl, D.E., Kirst, H.A., Cundliffe, E. Nat. Biotechnol. (2002) [Pubmed]
The structural basis for substrate anchoring, active site selectivity, and product formation by P450 PikC from Streptomyces venezuelae. Sherman, D.H., Li, S., Yermalitskaya, L.V., Kim, Y., Smith, J.A., Waterman, M.R., Podust, L.M. J. Biol. Chem. (2006) [Pubmed]
Characterization of the macrolide P-450 hydroxylase from Streptomyces venezuelae which converts narbomycin to picromycin. Betlach, M.C., Kealey, J.T., Ashley, G.W., McDaniel, R. Biochemistry (1998) [Pubmed]
Genetic architecture of the polyketide synthases for methymycin and pikromycin series macrolides. Xue, Y., Wilson, D., Sherman, D.H. Gene (2000) [Pubmed]
Interspecific protoplast fusion among macrolide-producing streptomycetes. Ikeda, H., Inoue, M., Tanaka, H., Omura, S. J. Antibiot. (1984) [Pubmed]

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