The incorporation of amino acids into the cell-wall mucopeptide of staphylococci and the effect of antibiotics on the process

Mandelstam, J.; Rogers, H. J.

doi:10.1042/bj0720654

Cited by 146 publications

(67 citation statements)

References 26 publications

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“…Park (1952) showed that penicillin caused accumulation of uridine-linked peptides which are believed to be precursors of cell-wall mucopeptide (Park & Strominger, 1957). Inhibition of mucopeptide synthesis by penicillin in washed staphylococci has been shown by Park (1958), Mandelstam & Rogers (1959) and Rogers & Jeljaszewicz (1961).…”

Section: Acid (Ampicillin)mentioning

confidence: 84%

“…There are, however, some noteworthy differences between the two types of mucopeptide. In none of the Gram-negative strains examined did the mucopeptide amount to more than about 1 % of the bacterial mass, whereas in Gram-positive organisms the mucopeptide is usually 10-20 % [see, for example, Mandelstam & Rogers (1959)]. Apart from being a minor constituent of the cell, the Gram-negative mucopeptide is also a small part of the wall.…”

Section: Discussionmentioning

confidence: 99%

“…The amino acid composition ot mucopeptide was determined with hydrolysed samples by quantitative paper chromatography, as described by Mandelstam & Rogers (1959). Chromatograms were developed for 2 days in butanol-acetio acid-water (63:10:27, by vol.).…”

Section: Analytical Method8mentioning

confidence: 99%

“…7 (Received 14 February 1962) Salton (1953) and Cummins & Harris (1956) showed that the cell walls of Gram-positive bacteria consisted mainly of polymers which were later called mucopeptides by Mandelstam & Rogers (1959). These always contained glucosamine, muramic acid, glutamic acid, alanine, either lysine or oce-diaminopimelic acid, and sometimes one or two additional amino acids.…”

Section: Preparation and Properties Of The Mucopeptides Ofmentioning

confidence: 99%

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Preparation and properties of the mucopeptides of cell walls of gram-negative bacteria

Mandelstam¹

1962

Biochemical Journal

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SUMMARY 1. In potassium-deficient barley plants 1,4-diauinobutane (putrescine), which had been previously characterized, occurs together with a Sakaguchi-and ninhydrin-positive compound, whose infrared spectrum and chromatographic properties are identical with those of 1-amino-4-guanidinobutane (agmatine).2. Agmatine and putrescine occur in potassiumdeficient red-clover plants.3. Under conditions of adequate potassium nutrition, agmatine and putrescine were found in barley and clover, and also in cabbage leaves, but the amounts were small relative to those in the potassium-deficient plants. 4. The putrescine concentration in barley seedlings was considerably increased by feeding with agmatine, a much smaller increase being induced by giving ornithine or arginine. Feeding with arginine increased the concentration of a Sakaguchipositive compound, which was chromatographically indistinguishable from agmatine.

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Section: Acid (Ampicillin)mentioning

confidence: 84%

Section: Discussionmentioning

confidence: 99%

Section: Analytical Method8mentioning

confidence: 99%

Section: Preparation and Properties Of The Mucopeptides Ofmentioning

confidence: 99%

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Preparation and properties of the mucopeptides of cell walls of gram-negative bacteria

Mandelstam¹

1962

Biochemical Journal

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“…Several effects, such as inhibition of induced enzyme synthesis and stimulation of efflux of K+ ions, could be ascribed to alterations in cell-membrane function. The antibiotic also inhibits incorporation of ['4C]aminoacids into cell walls and induces the accumulation of uridine-nucleotide precursors of the wall under conditions in which incorporation of amino acids into protein is unaffected (12)(13)(14)(15). However, since bacitracin affects protoplasts of bacteria, its action is not limited to effects on cell walls.…”

mentioning

confidence: 99%

Mechanism of Action of Bacitracin: Complexation with Metal Ion and C ₅₅ -Isoprenyl Pyrophosphate

Stone

Strominger

1971

Proc. Natl. Acad. Sci. U.S.A.

332

199

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The inhibition by bacitracin of the en- Bacitracin is an antibiotic produced by strains of Bacillus licheniformis. It is a mixture of closely related compounds, the main component of which (bacitracin A) is a cyclic polypeptide with a peptide side chain ( Fig. 1) (1-3). An unusual feature of the structure is the occurrence of a thiazoline ring formed between the L-cysteine and L-isoleucine residues at the N-terminal end of the acylic peptide side-chain. The free amino group of iisoleucine at the N-terminal end is adjacent to the thiazoline ring and is essential for antimicrobial activity. The transformation of bacitracin A to bacitracin F (in which the amino group is replaced by a carbonyl group) results in total loss of antimicrobial activity. A metal ion may be essential for the antimicrobial activity of bacitracin (4-1 1). The antimicrobial activity is stimulated by various metal ions and inhibited by metal-chelating agents, such as EDTA. Spectroscopic evidence for the interaction of bacitracin with metal ions has been obtained. The chelation may involve both the nitrogen of the thiazoline ring and the adjacent free amino-group in isoleucine; this chelation could assist in stabilizing the thiazoline ring, thus hindering the deamination to bacitracin F (10). It has been further postulated that in the zinc-bacitracin A complex, the zinc also coordinates through the imidazole of the histidine residue and the peptide nitrogen of the histidine residue, thus forming a oneto-one complex with bacitracin (10).Various biochemical lesions induced by bacitracin have been reported (9). Several effects, such as inhibition of induced enzyme synthesis and stimulation of efflux of K+ ions, could be ascribed to alterations in cell-membrane function. The antibiotic also inhibits incorporation of ['4C]aminoacids into cell walls and induces the accumulation of uridine-nucleotide precursors of the wall under conditions in which incorporation of amino acids into protein is unaffected (12-15). However, since bacitracin affects protoplasts of bacteria, its action is not limited to effects on cell walls. The precise site of action in cell wall synthesis has been defined as inhibition of the dephosphorylation of C55-isoprenyl pyrophosphate. This reaction is essential for regeneration of the lipid carrier required for the cyclic synthesis of peptidoglycan (16, 17). In the present paper, data are presented which suggest that bacitracin acts by forming a complex with C55-isoprenyl pyrophosphate (a component of the cell membrane) and divalent cations. The metal ion may serve as a bridge between the antibiotic and the substrate. MATERIALS AND METHODSThe C55-isoprenyl pyrophosphatase used was that present in membranes of Streptococcus fecalis. The membranes were prepared and washed with EDTA and 2 M LiCl as described previously (through step 2 of the procedure) (Staudenbauer, W. L., and J. L., Strominger, J. Biol. Chem., submitted). The residual LiCl was removed by washing with water and then dialysis against water. Finally, the memb...

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Bagshaped Macromolecules—A New Outlook on Bacterial Cell Walls

Weidel¹,

Pelzer²

1964

Advances in Enzymology - And Related Areas of Molecular Biology

206

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The incorporation of amino acids into the cell-wall mucopeptide of staphylococci and the effect of antibiotics on the process

Cited by 146 publications

References 26 publications

Preparation and properties of the mucopeptides of cell walls of gram-negative bacteria

Preparation and properties of the mucopeptides of cell walls of gram-negative bacteria

Mechanism of Action of Bacitracin: Complexation with Metal Ion and C ₅₅ -Isoprenyl Pyrophosphate

Bagshaped Macromolecules—A New Outlook on Bacterial Cell Walls

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The incorporation of amino acids into the cell-wall mucopeptide of staphylococci and the effect of antibiotics on the process

Cited by 146 publications

References 26 publications

Preparation and properties of the mucopeptides of cell walls of gram-negative bacteria

Preparation and properties of the mucopeptides of cell walls of gram-negative bacteria

Mechanism of Action of Bacitracin: Complexation with Metal Ion and C 55 -Isoprenyl Pyrophosphate

Bagshaped Macromolecules—A New Outlook on Bacterial Cell Walls

Contact Info

Product

Resources

About

Mechanism of Action of Bacitracin: Complexation with Metal Ion and C ₅₅ -Isoprenyl Pyrophosphate