Isopenicillin N N-acyltransferase

Isopenicillin N N-acyltransferase

isopenicillin N N-acyltransferase
Identifiers
EC number 2.3.1.164
CAS number 54576-90-8
Databases
IntEnz IntEnz view
BRENDA BRENDA entry
ExPASy NiceZyme view
KEGG KEGG entry
MetaCyc metabolic pathway
PRIAM profile
PDB structures RCSB PDB PDBe PDBsum
Gene Ontology AmiGO / EGO

In enzymology, an isopenicillin N N-acyltransferase (EC 2.3.1.164) is an enzyme that catalyzes the chemical reaction

phenylacetyl-CoA + isopenicillin N + H2O \rightleftharpoons CoA + penicillin G + L-2-aminohexanedioate

The 3 substrates of this enzyme are phenylacetyl-CoA, isopenicillin N, and H2O, whereas its 3 products are CoA, penicillin G, and L-2-aminohexanedioate.

This enzyme belongs to the family of transferases, specifically those acyltransferases transferring groups other than aminoacyl groups. The systematic name of this enzyme class is acyl-CoA:isopenicillin N N-acyltransferase. Other names in common use include acyl-coenzyme A:isopenicillin N acyltransferase, and isopenicillin N:acyl-CoA: acyltransferase. This enzyme participates in hydrophobic penicillins biosynthesis.

References

  • Tobin MB, Fleming MD, Skatrud PL, Miller JR (1990). "Molecular characterization of the acyl-coenzyme A:isopenicillin N acyltransferase gene (penDE) from Penicillium chrysogenum and Aspergillus nidulans and activity of recombinant enzyme in Escherichia coli". J. Bacteriol. 172 (10): 5908–14.  
  • Aplin RT, Baldwin JE, Roach PL, Robinson CV, Schofield CJ (Pt 2). "Investigations into the post-translational modification and mechanism of isopenicillin N:acyl-CoA acyltransferase using electrospray mass spectrometry". Biochem. J. 294: 357–63.  

Further reading

  • Aplin, Robin T.; Baldwin, Jack E.; Cole, Stephen C.J.; Sutherland, John D.; Tobin, Matthew B. (1993). "On the production of α,β-heterodimeric acyl-coenzyme A: isopenicillin N-acyltransferase of Penicillium chrysogenum". FEBS Letters 319 (1-2): 166–170.  
  • Fernández FJ, Gutierrez S, Velasco J, Montenegro E, Marcos AT, Martín JF (August 1994). "Molecular characterization of three loss-of-function mutations in the isopenicillin N-acyltransferase gene (penDE) of Penicillium chrysogenum".  
  • ALVAREZ, Emilio; MEESSCHAERT, Boudewijn; MONTENEGRO, Eduardo; GUTIERREZ, Santiago; DIEZ, Bruno; BARREDO, Jose L.; MARTIN, Juan F. (1993). "The isopenicillin-N acyltransferase of Penicillium chrysogenum has isopenicillin-N amidohydrolase, 6-aminopenicillanic acid acyltransferase and penicillin amidase activities, all of which are encoded by the single penDE gene". European Journal of Biochemistry 215 (2): 323–332.