Penicillin biosynthesis: conversion of deuteriated (L-α-amino-δ-adipyl)-L-cysteinyl-D-valine into isopenicillin N by a cell-free extract of Cephalosporium acremonium

1981 ◽  
pp. 246-247 ◽  
Author(s):  
Jack E. Baldwin ◽  
Mankil Jung ◽  
John J. Usher ◽  
Edward P. Abraham ◽  
Joyce A. Huddleston ◽  
...  
Keyword(s):  
Penicillin Biosynthesis ◽  
Cell Free Extract ◽  
Cephalosporium Acremonium ◽  
A Cell ◽  
Isopenicillin N

scholarly journals Incorporation of 3H from δ-(l-α-amino (4,5-3H)adipyl)-l-cysteinyl-d-(4,4-3H)valine into isopenicillin N

1979 ◽  
Vol 184 (2) ◽  
pp. 421-426 ◽  
Author(s):  
J O'Sullivan ◽  
R C Bleaney ◽  
J A Huddleston ◽  
E P Abraham
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Adipic Acid ◽  
Experimental Error ◽  
Acid Oxidase ◽  
Cephalosporium Acremonium ◽  
Amino Acid Oxidase ◽  
Free System ◽  
A Cell ◽  
Isopenicillin N

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.

Conversion of17O/18O-labelled δ-(L-α-aminoadipyl)–L-cycteinyl–D-valine into17O/18O-labelled isopenicillin N in a cell-free extract of C. acremonium

1982 ◽  
pp. 137-139 ◽  
Author(s):  
Robert M. Adlington ◽  
Robin T. Aplin ◽  
Jack E. Baldwin ◽  
Leslie D. Field ◽  
Eeva-M. M. John ◽  
...  
Keyword(s):  
Cell Free Extract ◽  
A Cell ◽  
Isopenicillin N

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
Keyword(s):  
Cephalosporium Acremonium ◽  
Free System ◽  
Cell Free System ◽  
A Cell ◽  
Osmotic Lysis ◽  
Isopenicillin N

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.

scholarly journals Cell-free conversion of isopenicillin N into deacetoxycephalosporin C by Cephalosporium acremonium mutant M-0198

1981 ◽  
Vol 194 (2) ◽  
pp. 649-651 ◽  
Author(s):  
J E Baldwin ◽  
J W Keeping ◽  
P D Singh ◽  
C A Vallejo
Keyword(s):  
High Pressure ◽  
Liquid Chromatography ◽  
High Pressure Liquid Chromatography ◽  
Cephalosporium Acremonium ◽  
Resistant Material ◽  
Free System ◽  
Cell Free System ◽  
Chromatography Analysis ◽  
A Cell ◽  
Isopenicillin N

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.

scholarly journals Synthesis of δ-(α-aminoadipyl)cysteinylvaline and its role in penicillin biosynthesis

1976 ◽  
Vol 157 (3) ◽  
pp. 651-660 ◽  
Author(s):  
P A Fawcett ◽  
J J Usher ◽  
J A Huddleston ◽  
R C Bleaney ◽  
J J Nisbet ◽  
...  
Keyword(s):  
Penicillium Chrysogenum ◽  
Methyl Groups ◽  
Penicillin Biosynthesis ◽  
Cephalosporium Acremonium ◽  
Free System ◽  
Cell Free System ◽  
A Cell

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.

Conversion of 17O/18O labelled δ-(L-α-aminoadlpyl)-L-cysteinyl-D-valine to 17O/18O labelled isopenicillin n in a cell-free extract of . A study by 17O-NMR spectroscopy and mass spectrometry

Tetrahedron ◽  
1983 ◽  
Vol 39 (7) ◽  
pp. 1061-1068 ◽  
Author(s):  
Robert M. Adlington ◽  
Robin T. Aplin ◽  
Jack E. Baldwin ◽  
Bulbul Chakravarti ◽  
Leslie D. Field ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Cell Free Extract ◽  
17O Nmr ◽  
A Cell ◽  
17O Nmr Spectroscopy ◽  
Isopenicillin N

scholarly journals A study of the biosynthesis of the tripeptide δ-(l-α-aminoadipyl)-l-cysteinyl-d-valine in a β-lactam-negative mutant of Cephalosporium acremonium

1983 ◽  
Vol 213 (3) ◽  
pp. 573-576 ◽  
Author(s):  
R M Adlington ◽  
J E Baldwin ◽  
M Lopez-Nieto ◽  
J A Murphy ◽  
N Patel
Keyword(s):  
Amino Acids ◽  
Cell Free Extract ◽  
Cephalosporium Acremonium ◽  
A Cell ◽  
Negative Mutant

A cell-free extract of Cephalosporium acremonium (Takeda N-2) was obtained that synthesized the tripeptide delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine and also the dipeptide delta-(L-alpha-aminoadipyl)-L-cysteine from the corresponding L-amino acids.

Conversion of 3-exomethylene cephalosporin C into deacetyl cephalosporin C in a cell-free extract from Cephalosporium acremonium(CW-19)

1983 ◽  
pp. 153 ◽  
Author(s):  
Robert M. Adlington ◽  
Jack E. Baldwin ◽  
Bulbul Chakravarti ◽  
Mankil Jung ◽  
Simon E. Moroney ◽  
...  
Keyword(s):  
Cephalosporin C ◽  
Cell Free Extract ◽  
Cephalosporium Acremonium ◽  
A Cell
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