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Chemical Compound Review

CPD-428     (3R,4S,5R,6S,7S,9R,11R,12S,13R ,14R)-14...

Synonyms: CHEBI:16089, SureCN12266551, AC1L3TMD, LMPK04000002, AR-1K9308, ...
 
 
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Disease relevance of 15797-36-1

 

High impact information on 15797-36-1

 

Chemical compound and disease context of 15797-36-1

  • The C-terminal region of a multifunctional polypeptide from the 6-deoxyerythronolide B synthase of Saccharopolyspora erythraea is predicted to contain an acyl carrier protein and a thioesterase or acyltransferase activity [Cortes, J., Haydock, S. F., Roberts, G. A., Bevitt, D. J. & Leadlay, P. F. (1990) Nature 348, 176-178] [8].
 

Biological context of 15797-36-1

 

Associations of 15797-36-1 with other chemical compounds

  • In the P450eryF/ketoconazole structure, the azole moiety and nearby rings of ketoconzole are positioned in the active site similar to the substrate, 6-deoxyerythronolide B, with the azole nitrogen atom coordinated to the heme iron atom [14].
  • The crystal structures of macrocycle-forming thioesterase (TE) domains from the picromycin synthase (PICS) and 6-deoxyerythronolide B synthase (DEBS) were determined to 1.8-3.0 A with an R(crys) of 19.2-24.4%, including three structures of PICS TE (crystallized at pH 7.6, 8.0, and 8.4) and a second crystal form of DEBS TE [15].
  • Erythronolide B, a presumed intermediate in the biosynthesis of the erythromycins, has been shown to be formed from 6-deoxyerythronolide B by hydroxylation at C-6 [16].
  • In vitro studies have previously demonstrated that the loading module of 6-deoxyerythronolide B synthase (DEBS) exhibits relaxed substrate specificity and is able to accept butyryl-CoA, leading to the production of polyketides with butyrate starter units [17].
  • Incubation of chirally deuterated NADPH with 6-deoxyerythronolide B synthase (DEBS) modules 5 and module 6 and analysis of the derived triketide lactones established that the two ketoreductase domains, KR5 and KR6, are both specific for the 4-pro-S hydride of the nicotinamide cofactor [18].
 

Gene context of 15797-36-1

 

Analytical, diagnostic and therapeutic context of 15797-36-1

References

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  2. A multiplasmid approach to preparing large libraries of polyketides. Xue, Q., Ashley, G., Hutchinson, C.R., Santi, D.V. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  3. Mechanism and specificity of the terminal thioesterase domain from the erythromycin polyketide synthase. Gokhale, R.S., Hunziker, D., Cane, D.E., Khosla, C. Chem. Biol. (1999) [Pubmed]
  4. Crystal structure of the macrocycle-forming thioesterase domain of the erythromycin polyketide synthase: versatility from a unique substrate channel. Tsai, S.C., Miercke, L.J., Krucinski, J., Gokhale, R., Chen, J.C., Foster, P.G., Cane, D.E., Khosla, C., Stroud, R.M. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  5. Crystal structures of the ferrous dioxygen complex of wild-type cytochrome P450eryF and its mutants, A245S and A245T: investigation of the proton transfer system in P450eryF. Nagano, S., Cupp-Vickery, J.R., Poulos, T.L. J. Biol. Chem. (2005) [Pubmed]
  6. Extender unit and acyl carrier protein specificity of ketosynthase domains of the 6-deoxyerythronolide B synthase. Chen, A.Y., Schnarr, N.A., Kim, C.Y., Cane, D.E., Khosla, C. J. Am. Chem. Soc. (2006) [Pubmed]
  7. Biochemical analysis of the substrate specificity of the beta-ketoacyl-acyl carrier protein synthase domain of module 2 of the erythromycin polyketide synthase. Wu, J., Kinoshita, K., Khosla, C., Cane, D.E. Biochemistry (2004) [Pubmed]
  8. An acyl-carrier-protein-thioesterase domain from the 6-deoxyerythronolide B synthase of Saccharopolyspora erythraea. High-level production, purification and characterisation in Escherichia coli. Caffrey, P., Green, B., Packman, L.C., Rawlings, B.J., Staunton, J., Leadlay, P.F. Eur. J. Biochem. (1991) [Pubmed]
  9. Alteration of the substrate specificity of a modular polyketide synthase acyltransferase domain through site-specific mutations. Reeves, C.D., Murli, S., Ashley, G.W., Piagentini, M., Hutchinson, C.R., McDaniel, R. Biochemistry (2001) [Pubmed]
  10. A model of structure and catalysis for ketoreductase domains in modular polyketide synthases. Reid, R., Piagentini, M., Rodriguez, E., Ashley, G., Viswanathan, N., Carney, J., Santi, D.V., Hutchinson, C.R., McDaniel, R. Biochemistry (2003) [Pubmed]
  11. Identification of DEBS 1, DEBS 2 and DEBS 3, the multienzyme polypeptides of the erythromycin-producing polyketide synthase from Saccharopolyspora erythraea. Caffrey, P., Bevitt, D.J., Staunton, J., Leadlay, P.F. FEBS Lett. (1992) [Pubmed]
  12. Organization of a cluster of erythromycin genes in Saccharopolyspora erythraea. Weber, J.M., Leung, J.O., Maine, G.T., Potenz, R.H., Paulus, T.J., DeWitt, J.P. J. Bacteriol. (1990) [Pubmed]
  13. Purification and reconstitution of the electron transport components for 6-deoxyerythronolide B hydroxylase, a cytochrome P-450 enzyme of macrolide antibiotic (erythromycin) biosynthesis. Shafiee, A., Hutchinson, C.R. J. Bacteriol. (1988) [Pubmed]
  14. Ketoconazole-induced conformational changes in the active site of cytochrome P450eryF. Cupp-Vickery, J.R., Garcia, C., Hofacre, A., McGee-Estrada, K. J. Mol. Biol. (2001) [Pubmed]
  15. Insights into channel architecture and substrate specificity from crystal structures of two macrocycle-forming thioesterases of modular polyketide synthases. Tsai, S.C., Lu, H., Cane, D.E., Khosla, C., Stroud, R.M. Biochemistry (2002) [Pubmed]
  16. Accumulation of 6-deoxyerythronolide B in a normal strain of Streptomyces erythreus and hydroxylation at carbon 6 of the erythranolide ring system by a soluble noninduced cell-free enzyme system. Corcoran, J.W., Vygantas, A.M. Biochemistry (1982) [Pubmed]
  17. 6-Deoxyerythronolide B analogue production in Escherichia coli through metabolic pathway engineering. Kennedy, J., Murli, S., Kealey, J.T. Biochemistry (2003) [Pubmed]
  18. Erythromycin biosynthesis. The 4-pro-S hydride of NADPH is utilized for ketoreduction by both module 5 and module 6 of the 6-deoxyerythronolide B synthase. Yin, Y., Gokhale, R., Khosla, C., Cane, D.E. Bioorg. Med. Chem. Lett. (2001) [Pubmed]
  19. API-mass spectrometry of polyketides. II. Fragmentation analysis of 6-deoxyerythronolide B analogs. Ashley, G.W., Carney, J.R. J. Antibiot. (2004) [Pubmed]
  20. Oxidation and electronic state dependence of proton transfer in the enzymatic cycle of cytochrome P450eryF. Harris, D.L. J. Inorg. Biochem. (2002) [Pubmed]
  21. Metabolic engineering of Escherichia coli for improved 6-deoxyerythronolide B production. Murli, S., Kennedy, J., Dayem, L.C., Carney, J.R., Kealey, J.T. J. Ind. Microbiol. Biotechnol. (2003) [Pubmed]
  22. Precursor-directed biosynthesis of 6-deoxyerythronolide B analogues is improved by removal of the initial catalytic sites of the polyketide synthase. Ward, S.L., Desai, R.P., Hu, Z., Gramajo, H., Katz, L. J. Ind. Microbiol. Biotechnol. (2007) [Pubmed]
  23. Intermodular communication in modular polyketide synthases: structural and mutational analysis of linker mediated protein-protein recognition. Kumar, P., Li, Q., Cane, D.E., Khosla, C. J. Am. Chem. Soc. (2003) [Pubmed]
  24. 6-Deoxyerythronolide-B synthase 2 from Saccharopolyspora erythraea. Cloning of the structural gene, sequence analysis and inferred domain structure of the multifunctional enzyme. Bevitt, D.J., Cortes, J., Haydock, S.F., Leadlay, P.F. Eur. J. Biochem. (1992) [Pubmed]
 
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