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Chemical Compound Review

Penicillin M     (2R,5R,6S)-6-[[(5S)-5-amino- 5-carboxy...

Synonyms: CHEBI:18165, AC1L99U1, C05557, 58678-43-6, IP1, ...
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Disease relevance of Penicillin M


High impact information on Penicillin M


Chemical compound and disease context of Penicillin M


Biological context of Penicillin M


Anatomical context of Penicillin M


Associations of Penicillin M with other chemical compounds


Gene context of Penicillin M

  • The PVA/U34 family is variable in sequence and exhibits great diversity in substrate specificity, to include enzymes such as choloyglycine hydrolases, acid ceramidases, isopenicillin N acyltransferases, and a subgroup of eukaryotic proteins with unclear function [27].
  • The Phl protein contains the peroxisome-targeting sequence that is also present in the isopenicillin N acyltransferase [28].

Analytical, diagnostic and therapeutic context of Penicillin M


  1. Isolation, sequence determination and expression in Escherichia coli of the isopenicillin N synthetase gene from Cephalosporium acremonium. Samson, S.M., Belagaje, R., Blankenship, D.T., Chapman, J.L., Perry, D., Skatrud, P.L., VanFrank, R.M., Abraham, E.P., Baldwin, J.E., Queener, S.W. Nature (1985) [Pubmed]
  2. Nucleotide sequence of the isopenicillin N synthase gene (pcbC) of the gram negative Flavobacterium sp. SC 12,154. Shiffman, D., Cohen, G., Aharonowitz, Y., Palissa, H., von Dohren, H., Kleinkauf, H., Mevarech, M. Nucleic Acids Res. (1990) [Pubmed]
  3. Purification of isopenicillin N synthetase. Pang, C.P., Chakravarti, B., Adlington, R.M., Ting, H.H., White, R.L., Jayatilake, G.S., Baldwin, J.E., Abraham, E.P. Biochem. J. (1984) [Pubmed]
  4. Large amplification of a 35-kb DNA fragment carrying two penicillin biosynthetic genes in high penicillin producing strains of Penicillium chrysogenum. Barredo, J.L., Díez, B., Alvarez, E., Martín, J.F. Curr. Genet. (1989) [Pubmed]
  5. Molecular analysis of the gene cluster involved in cephalosporin biosynthesis from Lysobacter lactamgenus YK90. Kimura, H., Izawa, M., Sumino, Y. Appl. Microbiol. Biotechnol. (1996) [Pubmed]
  6. Analyzing protein functions in four dimensions. Hajdu, J., Neutze, R., Sjögren, T., Edman, K., Szöke, A., Wilmouth, R.C., Wilmot, C.M. Nat. Struct. Biol. (2000) [Pubmed]
  7. Analysis of the role of cysteine residues in isopenicillin N synthetase activity by site-directed mutagenesis. Samson, S.M., Chapman, J.L., Belagaje, R., Queener, S.W., Ingolia, T.D. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  8. Mutational analysis and characterization of nocardicin C-9' epimerase. Kelly, W.L., Townsend, C.A. J. Biol. Chem. (2004) [Pubmed]
  9. A novel epimerization system in fungal secondary metabolism involved in the conversion of isopenicillin N into penicillin N in Acremonium chrysogenum. Ullan, R.V., Casqueiro, J., Banuelos, O., Fernandez, F.J., Gutierrez, S., Martin, J.F. J. Biol. Chem. (2002) [Pubmed]
  10. Ferrous active site of isopenicillin N synthase: genetic and sequence analysis of the endogenous ligands. Borovok, I., Landman, O., Kreisberg-Zakarin, R., Aharonowitz, Y., Cohen, G. Biochemistry (1996) [Pubmed]
  11. Cloning and characterization of the isopenicillin N synthase gene of Streptomyces griseus NRRL 3851 and studies of expression and complementation of the cephamycin pathway in Streptomyces clavuligerus. García-Domínguez, M., Liras, P., Martín, J.F. Antimicrob. Agents Chemother. (1991) [Pubmed]
  12. Isolation of deacetoxycephalosporin C from fermentation broths of Penicillium chrysogenum transformants: construction of a new fungal biosynthetic pathway. Cantwell, C., Beckmann, R., Whiteman, P., Queener, S.W., Abraham, E.P. Proc. Biol. Sci. (1992) [Pubmed]
  13. The beta-lactam biosynthesis genes for isopenicillin N epimerase and deacetoxycephalosporin C synthetase are expressed from a single transcript in Streptomyces clavuligerus. Kovacevic, S., Tobin, M.B., Miller, J.R. J. Bacteriol. (1990) [Pubmed]
  14. Replacement of tyrosine-197 and the corresponding tyrosine-195 to isoleucine in Cephalosporium acremonium and Streptomyces clavuligerus isopenicillin N synthase. Loke, P., Sim, T.S. Z. Naturforsch., C, J. Biosci. (2001) [Pubmed]
  15. Three binding sites for the Aspergillus nidulans PacC zinc-finger transcription factor are necessary and sufficient for regulation by ambient pH of the isopenicillin N synthase gene promoter. Espeso, E.A., Peñalva, M.A. J. Biol. Chem. (1996) [Pubmed]
  16. Characterization of a Penicillium chrysogenum gene encoding a PacC transcription factor and its binding sites in the divergent pcbAB-pcbC promoter of the penicillin biosynthetic cluster. Suárez, T., Peñalva, M.A. Mol. Microbiol. (1996) [Pubmed]
  17. Evolution of isopenicillin N synthase genes may have involved horizontal gene transfer. Landan, G., Cohen, G., Aharonowitz, Y., Shuali, Y., Graur, D., Shiffman, D. Mol. Biol. Evol. (1990) [Pubmed]
  18. Deacetylcephalosporin C Production in Penicillium chrysogenum by Expression of the Isopenicillin N Epimerization, Ring Expansion, and Acetylation Genes. Ullán, R.V., Campoy, S., Casqueiro, J., Fernández, F.J., Martín, J.F. Chem. Biol. (2007) [Pubmed]
  19. Incorporation of 3H from delta-(L-alpha-amino (4,5-3H)adipyl)-L-cysteinyl-D-(4,4-3H)valine into isopenicillin N. O'Sullivan, J., Bleaney, R.C., Huddleston, J.A., Abraham, E.P. Biochem. J. (1979) [Pubmed]
  20. Cell-free conversion of isopenicillin N into deacetoxycephalosporin C by Cephalosporium acremonium mutant M-0198. Baldwin, J.E., Keeping, J.W., Singh, P.D., Vallejo, C.A. Biochem. J. (1981) [Pubmed]
  21. Expression of genes and processing of enzymes for the biosynthesis of penicillins and cephalosporins. Martín, J.F., Gutiérrez, S., Fernández, F.J., Velasco, J., Fierro, F., Marcos, A.T., Kosalkova, K. Antonie Van Leeuwenhoek (1994) [Pubmed]
  22. High level expression in Escherichia coli of isopenicillin N synthase genes from Flavobacterium and Streptomyces, and recovery of active enzyme from inclusion bodies. Landman, O., Shiffman, D., Av-Gay, Y., Aharonowitz, Y., Cohen, G. FEMS Microbiol. Lett. (1991) [Pubmed]
  23. Oxygen activating nonheme iron enzymes. Lange, S.J., Que, L. Current opinion in chemical biology. (1998) [Pubmed]
  24. X-ray absorption studies of the ferrous active site of isopenicillin N synthase and related model complexes. Randall, C.R., Zang, Y., True, A.E., Que, L., Charnock, J.M., Garner, C.D., Fujishima, Y., Schofield, C.J., Baldwin, J.E. Biochemistry (1993) [Pubmed]
  25. Factors affecting the isopenicillin N synthetase reaction. Perry, D., Abraham, E.P., Baldwin, J.E. Biochem. J. (1988) [Pubmed]
  26. Cloning, sequencing and disruption of a gene from Streptomyces clavuligerus involved in clavulanic acid biosynthesis. Aidoo, K.A., Wong, A., Alexander, D.C., Rittammer, R.A., Jensen, S.E. Gene (1994) [Pubmed]
  27. Peptidase family U34 belongs to the superfamily of N-terminal nucleophile hydrolases. Pei, J., Grishin, N.V. Protein Sci. (2003) [Pubmed]
  28. Amplification and disruption of the phenylacetyl-CoA ligase gene of Penicillium chrysogenum encoding an aryl-capping enzyme that supplies phenylacetic acid to the isopenicillin N-acyltransferase. Lamas-Maceiras, M., Vaca, I., Rodríguez, E., Casqueiro, J., Martín, J.F. Biochem. J. (2006) [Pubmed]
  29. Biochemical characterization and molecular genetics of nine mutants of Penicillium chrysogenum impaired in penicillin biosynthesis. Cantoral, J.M., Gutiérrez, S., Fierro, F., Gil-Espinosa, S., van Liempt, H., Martín, J.F. J. Biol. Chem. (1993) [Pubmed]
  30. Crystallization and preliminary X-ray diffraction studies on a recombinant isopenicillin N synthase from Cephalosporium acremonium. Fujishima, Y., Nordlund, P., Pelosi, G., Schofield, C.J., Cole, S.J., Baldwin, J.E., Hajdu, J. J. Mol. Biol. (1994) [Pubmed]
  31. Thiolate ligation of the active site Fe2+ of isopenicillin N synthase derives from substrate rather than endogenous cysteine: spectroscopic studies of site-specific Cys----Ser mutated enzymes. Orville, A.M., Chen, V.J., Kriauciunas, A., Harpel, M.R., Fox, B.G., Münck, E., Lipscomb, J.D. Biochemistry (1992) [Pubmed]
  32. Site-directed mutagenesis of the active site serine290 in flavanone 3beta-hydroxylase from Petunia hybrida. Lukacin, R., Gröning, I., Pieper, U., Matern, U. Eur. J. Biochem. (2000) [Pubmed]
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