scholarly journals Conversion of isopenicillin N into penicillin N in cell-free extracts of Cephalosporium acremonium

1981 ◽  
Vol 194 (2) ◽  
pp. 645-647 ◽  
Author(s):  
G S Jayatilake ◽  
J A Huddleston ◽  
E P Abraham

In a cell-free system prepared by osmotic lysis of protoplasts of Cephalosporium acremonium, isopenicillin N is converted into penicillin N. The epimerase activity of the system is labile.

1981 ◽  
Vol 194 (2) ◽  
pp. 649-651 ◽  
Author(s):  
J E Baldwin ◽  
J W Keeping ◽  
P D Singh ◽  
C A Vallejo

In a cell-free system prepared by lysis of protoplasts of Cephalosporium acremonium mutant M-0198, isopenicillin N was converted into a penicillinase-resistant material that behaved like deacetoxycephalosporin C on high-pressure liquid chromatography analysis. This activity was found to be unstable to storage at -80 degrees C; 70-80% of the activity was lost after 1 day.


1979 ◽  
Vol 184 (2) ◽  
pp. 421-426 ◽  
Author(s):  
J O'Sullivan ◽  
R C Bleaney ◽  
J A Huddleston ◽  
E P Abraham

1. delta-(L-alpha-Amino[4,5-3H]adipyl)-L-cysteinyl-D-[4,4-3H]valine has been synthesized from its constituent amino acids, the L-alpha-amino[4,5-3H]adipic acid being obtained by reduction with 3H2 of methyl 5-acetamido-5,5-diethoxycarbonylpent-2-enoate and subsequent decarboxylation and hydrolysis. 2. In a cell-free system prepared by lysis of protoplasts of Cephalosporium acremonium 3H was incorporated from the doubly labelled tripeptide into a compound that behaved like penicillin N or isopenicillin N. The relative specific radioactivities of the alpha-aminoadipyl and penicillamine moieties of the penicillin were the same (within experimental error) as those of the alpha-aminoadipic acid and valine residues respectively of the tripeptide. 3. The behaviour of the labelled alpha-aminoadipic acid from the penicillin to the L-amino acid oxidase of Crotalus adamanteus venom showed that it was mainly L-alpha-aminoadipic acid. 4. The results are consistent with the hypothesis that the carbon skeleton of the LLD-tripeptide is incorporated intact into the penicillin molecule and that the first product is isopenicillin N.


1976 ◽  
Vol 157 (3) ◽  
pp. 651-660 ◽  
Author(s):  
P A Fawcett ◽  
J J Usher ◽  
J A Huddleston ◽  
R C Bleaney ◽  
J J Nisbet ◽  
...  

1. The stereoisomers of delta-(alpha-aminoadipyl)-L-cysteinylvaline (LLD, LLL and DLD) were synthesized from valine labelled with 3H in its methyl groups or in the alpha position. L-Cysteinyl-D-[4,4′-3H]valine was also synthesized. 2. 3H was incorporated into a compound that behaved like penicillin N when the LLD tripeptide containing either a methyl- or an alpha-labelled valine residue was incubated with a cell-free system prepared by lysis of protoplasts of Cephalosporium acremonium. 3. Incorporation was not observed under these conditions from the labelled all-L- or DLD-tripeptide, from L-cysteinyl-D-[4,4′-3H]valine, or of Penicillium chrysogenum appeared to be the LLD isomer, like that from C. acremonium. 5. These findings are discussed in relation to penicillin biosynthesis.


1982 ◽  
Vol 203 (3) ◽  
pp. 791-793 ◽  
Author(s):  
R L White ◽  
E M M John ◽  
J E Baldwin ◽  
E P Abraham

The biosynthesis of isopenicillin N from delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine in a cell-free system has been correlated wih O2 consumption by two methods, involving the use of an oxygen-electrode and an n.m.r. spectrometer respectively. The results are consistent with a 1 : 1 stoichiometric ratio for the dioxygen consumed to the isopenicillin N formed.


1982 ◽  
Vol 23 (6) ◽  
pp. 803-810
Author(s):  
S Hata ◽  
T Nishino ◽  
N Ariga ◽  
H Katsuki

1989 ◽  
Vol 264 (10) ◽  
pp. 5392-5399
Author(s):  
L S Mayorga ◽  
R Diaz ◽  
P D Stahl
Keyword(s):  

Sign in / Sign up

Export Citation Format

Share Document