Abstract
Vancomycin and ristocetin formed complexes on being mixed with mucopeptide precursors from various bacteria, as shown by chromatography, electrophoresis and differential ultraviolet spectra. Equimolar proportions of antibiotic and peptide were present. The specificity of the reaction was studied and the smallest molecule found to react was acetyl-d-alanyl-d-alanine. This C-terminal dipeptide sequence must be present for complex-formation; change of configuration or esterification prevented it. Modified vancomycins that retained antibiotic activity also combined with appropriate peptides. The dissociation constants of the more stable complexes were estimated from the differential-absorption results. The relationship of complex-formation to antibiotic action is discussed. Penicillin, supposed to be an analogue of acyl-d-alanyl-d-alanine, also modified the spectrum of vancomycin; so, too, did sodium benzylpenicilloate.
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- ANDERSON J. S., MATSUHASHI M., HASKIN M. A., STROMINGER J. L. LIPID-PHOSPHOACETYLMURAMYL-PENTAPEPTIDE AND LIPID-PHOSPHODISACCHARIDE-PENTAPEPTIDE: PRESUMED MEMBRANE TRANSPORT INTERMEDIATES IN CELL WALL SYNTHESIS. Proc Natl Acad Sci U S A. 1965 Apr;53:881–889. doi: 10.1073/pnas.53.4.881. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Anderson J. S., Matsuhashi M., Haskin M. A., Strominger J. L. Biosythesis of the peptidoglycan of bacterial cell walls. II. Phospholipid carriers in the reaction sequence. J Biol Chem. 1967 Jul 10;242(13):3180–3190. [PubMed] [Google Scholar]
- BREITENBACH J. W., DERKOSCH J., WESSELY F. Energetics of peptide formation. Nature. 1952 May 31;169(4309):922–922. doi: 10.1038/169922a0. [DOI] [PubMed] [Google Scholar]
- Best G. K., Durham N. N. Vancomycin adsorption to Bacillus subtilis cell walls. Arch Biochem Biophys. 1965 Sep;111(3):685–691. doi: 10.1016/0003-9861(65)90250-x. [DOI] [PubMed] [Google Scholar]
- Chatterjee A. N., Perkins H. R. Compounds formed between nucleotides related to the biosynthesis of bacterial cell wall and vancomycin. Biochem Biophys Res Commun. 1966 Aug 12;24(3):489–494. doi: 10.1016/0006-291x(66)90188-4. [DOI] [PubMed] [Google Scholar]
- Chatterjee A. N., Ward J. B., Perkins H. R. Synthesis of mucopeptide by L-form membranes. Nature. 1967 Jun 24;214(5095):1311–1314. doi: 10.1038/2141311a0. [DOI] [PubMed] [Google Scholar]
- Doyle R. J., Woodside E. E., Fishel C. W. Protein-polyelectrolyte interactions. The concanavalin A precipitin reaction with polyelectrolytes and polysaccharide derivatives. Biochem J. 1968 Jan;106(1):35–40. doi: 10.1042/bj1060035. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Ghuysen J. M., Bricas E., Leyh-Bouille M., Lache M., Shockman G. D. The peptide N alpha-(L-alanyl-D-isoglutaminyl)-N epsilon-(D-isoasparaginyl)-L-lysyl-D-alanine and the disaccharide N-acetylglucosaminyl-beta-1,4-N-acetylmuramic acid in cell wall peptidoglycan of Streptococcus faecalis strain ATCC 9790. Biochemistry. 1967 Aug;6(8):2607–2619. doi: 10.1021/bi00860a044. [DOI] [PubMed] [Google Scholar]
- Hughes R. C. The cell wall of Bacillus licheniformis N.C.T.C. 6346. Isolation of low-molecular-weight fragments from the soluble mucopeptide. Biochem J. 1968 Jan;106(1):49–59. doi: 10.1042/bj1060049. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Izaki K., Matsuhashi M., Strominger J. L. Biosynthesis of the peptidoglycan of bacterial cell walls. 8. Peptidoglycan transpeptidase and D-alanine carboxypeptidase: penicillin-sensitive enzymatic reaction in strains of Escherichia coli. J Biol Chem. 1968 Jun 10;243(11):3180–3192. [PubMed] [Google Scholar]
- Izaki K., Matsuhashi M., Strominger J. L. Glycopeptide transpeptidase and D-alanine carboxypeptidase: penicillin-sensitive enzymatic reactions. Proc Natl Acad Sci U S A. 1966 Mar;55(3):656–663. doi: 10.1073/pnas.55.3.656. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Izaki K., Strominger J. L. Biosynthesis of the peptidoglycan of bacterial cell walls. XIV. Purification and properties of two D-alanine carboxypeptidases from Escherichia coli. J Biol Chem. 1968 Jun 10;243(11):3193–3201. [PubMed] [Google Scholar]
- Katz W., Matsuhashi M., Dietrich C. P., Strominger J. L. Biosynthesis of the peptidoglycan of bacterial cell walls. IV. Incorporation of glycine in Micrococcus lysodeikticus. J Biol Chem. 1967 Jul 10;242(13):3207–3217. [PubMed] [Google Scholar]
- MARSHALL F. J. STRUCTURE STUDIES ON VANCOMYCIN. J Med Chem. 1965 Jan;8:18–22. doi: 10.1021/jm00325a004. [DOI] [PubMed] [Google Scholar]
- NEWTON G. G., ABRAHAM E. P. Degradation, structure and some derivatives of cephalosporin N. Biochem J. 1954 Sep;58(1):103–111. doi: 10.1042/bj0580103. [DOI] [PMC free article] [PubMed] [Google Scholar]
- PHILIP J. E., SCHENCK J. R., HARGIE M. P. Ristocetins A and B, two new antibiotics; isolation and properties. Antibiot Annu. 1956:699–705. [PubMed] [Google Scholar]
- Partridge S. M. Filter-paper partition chromatography of sugars: 1. General description and application to the qualitative analysis of sugars in apple juice, egg white and foetal blood of sheep. with a note by R. G. Westall. Biochem J. 1948;42(2):238–250. doi: 10.1042/bj0420238. [DOI] [PMC free article] [PubMed] [Google Scholar]
- REISSIG J. L., STORMINGER J. L., LELOIR L. F. A modified colorimetric method for the estimation of N-acetylamino sugars. J Biol Chem. 1955 Dec;217(2):959–966. [PubMed] [Google Scholar]
- REYNOLDS P. E. Studies on the mode of action of vancomycin. Biochim Biophys Acta. 1961 Sep 16;52:403–405. doi: 10.1016/0006-3002(61)90698-9. [DOI] [PubMed] [Google Scholar]
- Schechter I., Berger A. Peptides of L-and D-alanine. Synthesis and optical rotations. Biochemistry. 1966 Oct;5(10):3362–3370. doi: 10.1021/bi00874a040. [DOI] [PubMed] [Google Scholar]
- Tipper D. J., Strominger J. L. Biosynthesis of the peptidoglycan of bacterial cell walls. XII. Inhibition of cross-linking by penicillins and cephalosporins: studies in Staphylococcus aureus in vivo. J Biol Chem. 1968 Jun 10;243(11):3169–3179. [PubMed] [Google Scholar]
- Tipper D. J., Strominger J. L. Mechanism of action of penicillins: a proposal based on their structural similarity to acyl-D-alanyl-D-alanine. Proc Natl Acad Sci U S A. 1965 Oct;54(4):1133–1141. doi: 10.1073/pnas.54.4.1133. [DOI] [PMC free article] [PubMed] [Google Scholar]
- WALLAS C. H., STROMINGER J. L. Ristocetins, inhibitors of cell wall synthesis in Staphylococcus aureus. J Biol Chem. 1963 Jul;238:2264–2266. [PubMed] [Google Scholar]
- WEIDEL W., PELZER H. BAGSHAPED MACROMOLECULES--A NEW OUTLOOK ON BACTERIAL CELL WALLS. Adv Enzymol Relat Areas Mol Biol. 1964;26:193–232. doi: 10.1002/9780470122716.ch5. [DOI] [PubMed] [Google Scholar]