Deacetoxycephalosporin-C synthase explained

deacetoxycephalosporin-C synthase
Ec Number:	1.14.20.1
Cas Number:	85746-10-7
Go Code:	0050599

In enzymology, a deacetoxycephalosporin-C synthase is an enzyme that catalyzes the chemical reaction

penicillin N + 2-oxoglutarate + O₂

\rightleftharpoons deacetoxycephalosporin C + succinate + CO₂ + H₂O

The 3 substrates of this enzyme are penicillin N, 2-oxoglutarate, and O₂, whereas its 4 products are deacetoxycephalosporin C, succinate, CO₂, and H₂O.

Classification

This enzyme belongs to the family of oxidoreductases, specifically those acting on paired donors, with O2 as oxidant and incorporation or reduction of oxygen. The oxygen incorporated need not be derived from O2 with 2-oxoglutarate as one donor, and the other dehydrogenated.

Nomenclature

The systematic name of this enzyme class is penicillin-N,2-oxoglutarate:oxygen oxidoreductase (ring-expanding). Other names in common use include DAOCS, penicillin N expandase, and DAOC synthase.

Biological role

This enzyme participates in penicillin and cephalosporin biosynthesis.

Structural studies

As of late 2007, 7 structures have been solved for this class of enzymes, with PDB accession codes,,,,,, and .

References

• Cantwell C, Beckmann R, Whiteman P, Queener SW, Abraham EP . 1992 . Isolation of deacetoxycephalosporin C from fermentation broths of Penicillium chrysogenum transformants: construction of a new fungal biosynthetic pathway . . 248 . 283 - 9 . 1354366 . 10.1098/rspb.1992.0073 . 1323 . 1992RSPSB.248..283C . 40424189 .
• Lee HJ, Lloyd MD, Harlos K, Clifton IJ, Baldwin JE, Schofield CJ . 2001 . Kinetic and crystallographic studies on deacetoxycephalosporin C synthase (DAOCS) . J. Mol. Biol. . 308 . 937 - 48 . 11352583 . 10.1006/jmbi.2001.4649 . 5 .
• Yeh WK, Ghag SK, Queener SW . 1992 . Enzymes for epimerization of isopenicillin N, ring expansion of penicillin N, and 3'-hydroxylation of deacetoxycephalosporin C Function, evolution, refolding, and enzyme engineering . Ann. N.Y. Acad. Sci. . 672 . 396 - 408 . 10.1111/j.1749-6632.1992.tb32705.x .
• Andersson I . 1998 . Structure of a cephalosporin synthase . Nature . 394 . 805 - 9 . 9723623 . 10.1038/29575 . Van Scheltinga . AC . Lloyd . MD . Hara . T . Ramaswamy . S . Perrakis . A . Thompson . A . Lee . HJ . Baldwin . JE . Lee . Hwei-Jen . Baldwin . Jack E. . Hajdu . Janos . 6695 . 1998Natur.394..805V . 4361123 . 8 .
• Dotzlaf JE, Yeh WK . 1989 . Purification and properties of deacetoxycephalosporin C synthase from recombinant Escherichia coli and its comparison with the native enzyme purified from Streptomyces clavuligerus . J. Biol. Chem. . 264 . 10219 - 27 . 2656705 . 17 .