title: Elucidation of conditions allowing conversion of penicillin G and other penicillins to deacetoxycephalosporins by resting cells and extracts of Streptomyces clavuligerus NP1.
abstract: Using resting cells and extracts of Streptomyces clavuligerus NP1, we have been able to convert penicillin G (benzylpenicillin) to deacetoxycephalosporin G. Conversion was achieved by increasing by 45x the concentration of FeSO4 (1.8 mM) and doubling the concentration of alpha-ketoglutarate (1.28 mM) as compared with standard conditions used for the normal cell-free conversion of penicillin N to deacetoxycephalosporin C. ATP, MgSO4, KCl, and DTT, important in cell-free expansion of penicillin N, did not play a significant role in the ring expansion of penicillin G by resting cells or cell-free extracts. When these conditions were used with 14 other penicillins, ring expansion was achieved in all cases.
authors.affiliation: Fermentation Microbiology Laboratory, Department of Biology, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
authors.forename: H
authors.initials: H
authors.lastname: Cho
authors.forename: J L
authors.initials: JL
authors.lastname: Adrio
authors.forename: J M
authors.initials: JM
authors.lastname: Luengo
authors.forename: S
authors.initials: S
authors.lastname: Wolfe
authors.forename: S
authors.initials: S
authors.lastname: Ocran
authors.forename: G
authors.initials: G
authors.lastname: Hintermann
authors.forename: J M
authors.initials: JM
authors.lastname: Piret
authors.forename: A L
authors.initials: AL
authors.lastname: Demain
mesh_terms: D000255:Adenosine Triphosphate / Q000494:pharmacology; D001205:Ascorbic Acid / Q000494:pharmacology; D002511:Cephalosporins / Q000378:metabolism*; D015169:Colony Count, Microbial; D004229:Dithiothreitol / Q000494:pharmacology; D005296:Ferrous Compounds / Q000494:pharmacology; D007399:Interphase; D019751:Intramolecular Transferases / Q000378:metabolism; D007656:Ketoglutaric Acids / Q000494:pharmacology; D007700:Kinetics; D008278:Magnesium Sulfate / Q000494:pharmacology; D010400:Penicillin G / Q000378:metabolism*; D046915:Penicillin-Binding Proteins; D010406:Penicillins / Q000378:metabolism*; D011189:Potassium Chloride / Q000494:pharmacology; D013302:Streptomyces / Q000166:cytology / Q000187:drug effects / Q000378:metabolism*
chemical_list: D002511:Cephalosporins; D005296:Ferrous Compounds; D007656:Ketoglutaric Acids; D046915:Penicillin-Binding Proteins; D010406:Penicillins; C025578:deacetoxycephalosporin C; C020748:ferrous sulfate; D011189:Potassium Chloride; D008278:Magnesium Sulfate; D000255:Adenosine Triphosphate; D019751:Intramolecular Transferases; C038371:deacetoxycephalosporin C synthetase; C006414:penicillin N; D001205:Ascorbic Acid; D010400:Penicillin G; D004229:Dithiothreitol