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At least 19 recordsLinked to original sources
PubMed1977

Muramic acid as a measure of microbial biomass in estuarine and marine samples.

Muramic acid, a component of the muramyl peptide found only in the cell walls of bacteria and blue-green algae, furnishes a measure of detrital or sedimentary procaryotic biomass. A reproducible assay involving acid hydrolysis, preparative thin-layer chromatographic purification, and colorimetric analysis of lactate released from muramic acid by alkaline hydrolysis is described. Comparison of semitropical estuarine detritus, estuarine muds, and sediments from anaerobic Black Sea cores showed muramic acid levels of 100 to 700 microng/g (dry weight), 34 microng/g, and 1.5 to 14.9 microng/g, respectively. Enzymatic assays of lactate from muramic acid gave results 10- to 20-fold higher. Radioactive pulse-labeling studies showed that [14C]acetate is rapidly incorporated into muramic acid by the detrital microflora. Subsequent loss of 14C, accompanied by nearly constant levels of total muramic acid, indicated active metabolism in procaryotic cell walls.

Acetates↗
PubMed1989

Mass spectrometric quantitation of muramic acid, a bacterial cell wall component, in septic synovial fluids.

This is the first report describing the use of gas chromatography-mass spectrometry for detection of muramic acid in infected synovial fluid (SF). Muramic acid is a ubiquitous component of bacterial cell walls, and it has been proposed that it could serve as a chemical marker for the presence of live bacteria or bacterial debris in rheumatoid joints. Our goal was to determine whether muramic acid was present at detectable levels in septic SF, since this would serve as a positive control for studies of reactive and rheumatoid arthritis. Muramic acid was found to be present at levels of less than 250-1,700 ng/ml in 12 septic SF samples (10 of which were culture positive for Staphylococcus aureus and 1 each for Escherichia coli and Streptococcus pneumoniae). Among these samples, those containing low bacterial colony counts did not contain detectable muramic acid. Muramic acid was also not detected in any SF samples from 20 control patients. We conclude that muramic acid can be used as a marker for the presence of bacterial peptidoglycan in SF. With further lowering of gas chromatography-mass spectrometry detection limits, determination of the quantities of bacterial debris present in joints of patients with rheumatoid or reactive arthritis will be attainable.

Cell Wall↗
PubMed1991

Legume lectins interact with muramic acid and N-acetylmuramic acid.

The inhibitory potency of both muramic acid (MurAc) and N-acetylmuramic acid (MurNAc) on various legume lectins, including Glc/Man- and Gal/GalNAc-specific lectins, was investigated by a haemagglutination inhibition technique. Data indicated that many lectins, especially those specific for Glc/Man, specifically interact with MurAc and MurNAc often to a greater extent than with other monosaccharides and their derivatives, such as N-acetylglucosamine (GlcNAc) and sialic acid. Glc/Man-specific lectins were also shown to interact with the muramyl-dipeptide MurNAc-D-Ala-D-isoGln. These interactions could explain why various lectins readily agglutinate some bacterial strains of which cell walls contain peptidoglycans with high amounts of MurNAc.

Carbohydrate Sequence↗
PubMed1985

Modifications in the alditol acetate method for analysis of muramic acid and other neutral and amino sugars by capillary gas chromatography-mass spectrometry with selected ion monitoring.

Two alditol acetate methods for the gas chromatographic (GC) analysis of neutral and amino sugars were compared. Following sodium borohydride reduction, one method uses methylimidazole as an acetylation catalyst without prior removal of water or borate salts and the other method uses sodium acetate after removal of borate and water. Depending on the acetylation conditions, muramic acid produced different derivatives. With methylimidazole, reliable derivatization of muramic acid was not possible, although other sugars derivatized reliably. With sodium acetate, all sugars tested were reproducibly derivatized. The utility of the sodium acetate method is shown by the trace GC-mass spectrometric analysis of muramic acid and rhamnose derived from bacterial peptidoglycan-polysaccharide complexes in mammalian tissue.

Acetylation↗
PubMed1967

Biosynthesis of streptococcal cell walls: N-acetyl-D-muramic acid.

Glucose-1-(14)C and acetylglucosamine-1-(14)C were added singly and together with equal amounts of the unlabeled reciprocal to Brain Heart Infusion and used for the culture of Streptococcus pyogenes. The labeling pattern of the rhamnose, glucosamine, and muramic acid in the cell wall supported an intermediary role for acetylglucosamine in providing the C1-C6 moiety of muramic acid. Although radioactivity in the C2-C9 portion of muramic acid suggested that some of the lactyl group (C7-C9) came from glycolytic products, there was also considerable contribution to it from noncarbohydrate sources. Using cell-free extracts, we were unable to demonstrate biosynthesis of acetylmuramic acid, either free or nucleotide-bound, while glycolysis was occurring. The formation of uridine diphosphoacetylmuramic acid has been reported by others who used uridine diphospho-N-acetyl-d-glucosamine, phosphoenolpyruvate, reduced nicotinamide adenine dinucleotide, and reduced nicotinamide adenine dinucleotide phosphate. However, we did not detect the formation of this compound.

Acids↗
PubMed1969

Structure of the peptidoglycan of bacterial spores: occurrence of the lactam of muramic acid.

Six major oligosaccharides were released from the peptidoglycan of spores of Bacillus subtilis by lysozyme treatment. They were isolated and characterized as a disaccharide, tetrasaccharide, and hexasaccharide composed of equal amounts of muramic acid and glucosamine and containing two, three, and four acetyl groups, respectively. Three of the compounds were substituted by a single L-alanine residue, and the other three by a single tetrapeptide substituent on the acetylmuramic acid residue at the reducing end of each compound. The other muramic acid residue in the tetrasaccharides (and two of the three in the hexasaccharides) were shown to be present as muramic lactams, a sugar not previously found in nature and, hence, a unique spore constituent. Other features of the structure of spore peptidoglycan are discussed.

Bacillus subtilis↗
PubMed1968

Structure of the cell wall of Lactobacilli. Role of muramic acid phosphate in Lactobacillus fermenti.

1. The polysaccharide and mucopeptide components of the cell wall of Lactobacillus fermenti, serological group F, were separated by mild conditions of acid hydrolysis; the polysaccharide was composed of glucose and galactose. 2. Soluble cell-wall products were isolated from cell wall lysed by lysozyme and a Streptomyces enzyme preparation. The lysozyme-dissolved fraction contained a greater proportion of mucopeptide. 3. The soluble preparations were heated in dilute acid to hydrolyse the linkage between the polysaccharide and mucopeptide components and then incubated with acid phosphatase. 4. Inorganic phosphate was released from products of Streptomyces enzyme action but not from products of lysozyme action. 5. The phosphate was shown to be present in the mucopeptide as muramic acid phosphate. It is concluded that in the intact wall polysaccharide is joined to muramic acid by a phosphodiester linkage.

Acid Phosphatase↗
PubMed1992

Assay for N-acetylmuramyl-L-alanine amidase in serum by determination of muramic acid released from the peptidoglycan of Brevibacterium divaricatum.

A method is reported for the determination of N-acetylmuramyl-L-alanine amidase in serum. Muramic acid, released from the interpeptide bridges of Brevibacterium divaricatum peptidoglycan, is measured by a modified colorimetric method. Using this procedure, it was possible to determine N-acetylmuramyl-L-alanine amidase in aliquots of less than 10 microliters human serum with an incubation time of 10 min. Amidase activity was found in all the sera tested (n = 11). The relevance of this simple and fast assay is discussed.

Adult↗
PubMed1990

Muramic acid is not detectable in Chlamydia psittaci or Chlamydia trachomatis by gas chromatography-mass spectrometry.

By using the powerful separation technique of capillary gas chromatography combined with the selectivity of mass spectrometric detection, muramic acid was not detectable in purified elementary bodies of Chlamydia psittaci Cal 10 (less than or equal to 0.006%) or C. trachomatis serovar E (less than or equal to 0.02%). This confirms previous reports which suggested the absence of a typical peptidoglycan in Chlamydia spp.

Chlamydia trachomatis↗
PubMed1968

Determination of amino sugars in mixtures containing glucosamine, galactosamine and muramic acid.

A colorimetric method is described whereby the direct quantitative determination of glucosamine, galactosamine and muramic acid can be achieved without previous treatment of the cell-wall hydrolysate, for example by column chromatography. Molar ratios of hexosamines in cell-wall preparations, from a number of bacterial species, determined by this method were found to be in general agreement with previously published results.

Amino Sugars↗
PubMed1990

Muramic acid derivatives as glycosyl donors for the synthesis of muramyl-containing glycosphingolipids and fatty acids.

2-Azido-2-deoxy-4,6-O-isopropylidene-3-O-[(1R)-(methoxycarbonyl)ethyl]- alpha-D-glucopyranosyl trichloroacetimidate (3 alpha) has been used as the glycosyl donor in the synthesis of glycosphingolipids 14 and 27. Reaction of 3 alpha with (2S, 3R, 4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol (6) gave (2S, 3R, 4E)-2-azido-1-(2-azido-2-deoxy-4,6-O-isopropylidene-3-O-[(1R)-1-(m ethoxycarbonyl)ethyl]-beta-D-glucopyranosyloxyl)-3-benzoyloxy-4- octadecene (7), which was converted into (2S, 3R, 4E)-1-(2-deoxy-2-hexadecanoylamino-3-O-[(2R)-propanoyl-(L-alanyl-D -isoglutamine benzyl ester)-2-yl]-beta-D-glucopyranosyloxy)-2-hexadecanoylamino-4-oc tadecen-ol (14). Reaction of 3 alpha with tert-butyldimethylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside (15) gave tert-butyldimethylsilyl 2-azido-4-O-(2-azido-2-deoxy-4,6-O-isopropylidene-3-O-[(1R)-1-(methox ycarbonyl)ethyl]-beta-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-be ta- D-gluc opyranoside (16 beta), which was converted into 1,3,6-tri-O-acetyl-2-deoxy-4-O-(4,6-di-O-acetyl-2-deoxy-2-hexadecanoy lam ino-3-O-[2R)-propanoyl-(L-alanyl-D-isoglutamine methyl ester)-2-yl]-beta-D-glucopyranosyl)-2-hexadecanoylamino-D-glucopyranose (27).

Carbohydrate Sequence↗