Home LiteratureArticle Details
PMID: 629760 Published · ppublish English Journal Article

Preferential nitration with tetranitromethane of a specific tyrosine residue in penicillinase from Staphylococcus aureus PCl. Evidence that the preferentially nitrated residue is not part of the active site but that loss of activity is due to intermolecular cross-linking.

The Biochemical journal ·Vol. 169 ·No. 2 ·1978-02-01 ·Pages 381-8

Bristow AF, Virden R

Abstract

1. Nitration of tyrosine residues of staphylococal penicillinase was accompanied by a partial loss of enzymic activity, which was not readily explained by nitration of a single residue. 2. Loss of activity correlated with low recovery of tyrosine plus nitrotyrosine, which was consistent with cross-linking. 3. The fraction of treated enzyme that was eluted from Sephadex G-75 earlier than native penicillinase was similar to the fraction of enzyme activity lost. Protein eluted in positions corresponding to monomer, dimer and higher oligomers respectively showed major bands in corresponding positions in sodium dodecyl sulphate/polyacrylamide-gel electrophoresis, indicating that the increase in molecular weight was due to intermolecular cross-linking. Monomeric enzyme containing up to 4 mol of nitrotyrosine/mol retained full catalytic activity. Dimeric enzyme retained 50% of normal activity, whereas higher oligomers retained an average of 8-15% of normal activity. 4. Monomeric enzyme isolated after treatment with equimolar tetranitromethane was nitrated predominantly at tyrosine-72.5. Reaction of reduced nitrated monomer with 1,5-difluoro-2,4-dinitrobenzene gave a monomeric, apparently cross-linked product with full catalytic activity. 6. It is concluded that tyrosine-72 plays no part in the active site. Its preferential nitration may be due to its being insufficiently exposed to be available for intermolecular cross-linking. This poperty may make it useful for attachment of a reporter group.

MeSH Terms
Amino Acids/analysis Binding Sites Chemical Phenomena Chemistry Dinitrofluorobenzene/pharmacology Enzyme Activation/drug effects Methane/analogs & derivatives Penicillinase/metabolism Peptide Fragments/analysis Staphylococcus aureus/enzymology Tetranitromethane/pharmacology Tyrosine/metabolism beta-Lactamase Inhibitors
Chemicals
Amino Acids Peptide Fragments beta-Lactamase Inhibitors Tyrosine Dinitrofluorobenzene Penicillinase Tetranitromethane Methane
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Bristow A F
Virden R
References (18)
18 references, click to expand
  1. PURIFICATION AND PROPERTIES OF THE EXOPENICILLINASE FROM STAPHYLOCOCCUS AUREUS.
    Biochem J. 1963 Sep;88:452-9 PMID: 14071518
  2. Halogenation of tyrosine during acid hydrolysis.
    Biochim Biophys Acta. 1963 May 14;71:468-71 PMID: 13976292
  3. Crosslinking during the nitration of bovine insulin with tetranitromethane.
    Biochem Biophys Res Commun. 1970 Feb 20;38(4):678-82 PMID: 5462700
  4. Sequence analysis of fluorescamine-stained peptides and proteins purified on a nanomole scale. Application to proteins of bacteriophage MS2.
    Eur J Biochem. 1974 May 2;44(1):279-88 PMID: 4854242
  5. Reaction of tetranitromethane with sulfhydryl groups in proteins.
    Biochemistry. 1969 Dec;8(12):4740-5 PMID: 4904041
  6. Probable protein crosslinking with tetranitromethane.
    Biochim Biophys Acta. 1968 Jun 26;160(2):274-6 PMID: 4173111
  7. Identification of neighbor relationships among proteins in the 30 S ribosome: intermolecular cross-linkage of three proteins induced by tetranitromethane.
    J Mol Biol. 1973 Aug 25;78(4):651-63 PMID: 4587133
  8. L-asparaginase from Escherichia coli B. Chemical modifications of tyrosyl residues.
    J Biol Chem. 1972 Jul 10;247(13):4121-5 PMID: 4556304
  9. Polymerization of papain by the reaction of its tyrosine residues with tetranitromethane.
    J Biochem. 1974 Jun;75(6):1377-80 PMID: 4426897
  10. Measurement of molecular weights by electrophoresis on SDS-acrylamide gel.
    Methods Enzymol. 1972;26:3-27 PMID: 4680711
  11. The mechanism of folding of globular proteins. Suitability of a penicillinase from Staphylococcus Aureus as a model for refolding studies.
    Biochem J. 1976 May 1;155(2):325-30 PMID: 938483
  12. The amino acid sequence of Staphylococcus aureus penicillinase.
    Biochem J. 1975 Nov;151(2):197-218 PMID: 1218078
  13. The cross-linking of tyrosine by treatment with tetranitromethane.
    Biochem J. 1971 Jan;121(2):203-9 PMID: 5117027
  14. Chemical modification of human lysozyme. Acetylation and nitration of tyrosine.
    Can J Biochem. 1971 Jul;49(7):816-21 PMID: 5557892
  15. On the use of tetranitromethane as a nitration reagent. The reaction of phenol side-chains in bovine and porcine trypsinogens and trypsins.
    Eur J Biochem. 1970 Feb;12(2):250-7 PMID: 5466620
  16. Cross-linking of aminotyrosyl residues in the active site of staphylococcal nuclease.
    J Biol Chem. 1969 Jan 25;244(2):406-12 PMID: 5773305
  17. The tyrosyl residues at the active site of staphylococcal nuclease. Modifications by tetranitromethane.
    J Biol Chem. 1968 Sep 25;243(18):4787-98 PMID: 5687721
  18. Environmentally sensitive tyrosyl residues. Nitration with tetranitromethane.
    Biochemistry. 1967 Jan;6(1):358-61 PMID: 6030334
Article Info
Journal
The Biochemical journal
Abbr.
Biochem J
ISSN
0264-6021
Published
1978-02-01
Pages
381-8
Language
English
Region
England
NLM ID
2984726R
PMCID
PMC1184177
Subset
IM
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: [email protected]