The biosynthetic implications of acetate and glutamate incorporation into (3R,5R)-carbapenam-3-carboxylic acid and (5R)-carbapen-2-em-3-carboxylic acid by Serratia sp.
Two new beta-lactams have been isolated from strains of Serratia and Erwinia sp. and identified as (3R,5R)- and (3S,5R)-carbapenam-3-carboxylic acid. These novel carbapenams lack antibacterial activity, are resistant to both beta-lactamases I and II from Bacillus cereus and are not detected by the lactamase induction assay. Radiolabelled and stable isotope experiments have established that both metabolites together with the antibiotic 5R-carbapenem-3-carboxylic acid are glutamate and acetate derived. A number of possible pathways for the biosynthesis of these compounds as well as their relationship to the more complex members of the carbapenem family of beta-lactam antibiotics are discussed.
Bycroft
B W
BW
Department of Pharmaceutical Sciences, University of Nottingham, UK.
Maslen
C
C
Box
S J
SJ
Brown
A
A
Tyler
J W
JW
D000085:Acetates / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D015780:Carbapenems; D002247:Carbon Isotopes; D002250:Carbon Radioisotopes; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D005971:Glutamates / Q000378:metabolism*; D007769:Lactams; D012705:Serratia / Q000378:metabolism*; D013237:Stereoisomerism
D000085:Acetates; D000900:Anti-Bacterial Agents; D015780:Carbapenems; D002247:Carbon Isotopes; D002250:Carbon Radioisotopes; D005971:Glutamates; D007769:Lactams; C057567:carbapenam-3-carboxylic acid; C035629:carbapenem-3-carboxylic acid