scholarly journals Metabolic Incorporation of N ‐Acetyl Muramic Acid Probes into Bacterial Peptidoglycan

2019 ◽  
Vol 11 (4) ◽  
Author(s):  
Kristen E. DeMeester ◽  
Hai Liang ◽  
Junhui Zhou ◽  
Kimberly A. Wodzanowski ◽  
Benjamin L. Prather ◽  
...  
Keyword(s):  
Muramic Acid ◽  
Bacterial Peptidoglycan

Protected N-Acetyl Muramic Acid Probes Improve Bacterial Peptidoglycan Incorporation via Metabolic Labeling

2021 ◽  
Author(s):  
Ashley R. Brown ◽  
Kimberly A. Wodzanowski ◽  
Cintia C. Santiago ◽  
Stephen N. Hyland ◽  
Julianna L. Follmar ◽  
...  
Keyword(s):  
Metabolic Labeling ◽  
Muramic Acid ◽  
Bacterial Peptidoglycan

Structure of muramic acid TMS derivative mass spectrum's base ion (m/z=185) used for quantification of bacterial peptidoglycan

2002 ◽  
Vol 48 (2-3) ◽  
pp. 267-270 ◽  
Author(s):  
Karol Bal ◽  
Lennart Larsson ◽  
Eugenia Mielniczuk ◽  
Zbigniew Mielniczuk
Keyword(s):  
Muramic Acid ◽  
Bacterial Peptidoglycan

scholarly journals Characterization of the Microbial Community in Indoor Environments: a Chemical-Analytical Approach

2003 ◽  
Vol 69 (6) ◽  
pp. 3103-3109 ◽  
Author(s):  
Aleksandra Sebastian ◽  
Lennart Larsson
Keyword(s):  
Fatty Acids ◽  
Ion Trap ◽  
Internal Standard ◽  
Indoor Environments ◽  
Muramic Acid ◽  
Gram Positive Bacteria ◽  
Branched Chain Fatty Acids ◽  
Branched Chain ◽  
Bacterial Peptidoglycan ◽  
Chain Fatty Acids

ABSTRACT An integrated procedure is presented whereby gas chromatography-ion trap mass spectrometry is used to determine chemical markers of gram-negative bacterial lipopolysaccharide (3-hydroxy fatty acids with 10 to 18 carbon atoms), gram-positive bacteria (branched-chain fatty acids with 15 and 17 carbon atoms), bacterial peptidoglycan (muramic acid), and fungal biomass (ergosterol) in samples of settled house dust. A hydrolysate of 13C-labeled cyanobacterial cells is used as an internal standard for the first three markers. These analyses require two dust samples, one for 3-OH fatty acids, branched-chain fatty acids, and muramic acid and another for ergosterol. The method may be used to characterize microbial communities in environmental samples.

scholarly journals Central pyrogenic activity of muramyl dipeptide.

1980 ◽  
Vol 152 (4) ◽  
pp. 869-877 ◽  
Author(s):  
G Riveau ◽  
K Masek ◽  
M Parant ◽  
L Chedid
Keyword(s):  
Cerebrospinal Fluid ◽  
Muramyl Dipeptide ◽  
Intracerebroventricular Administration ◽  
Muramic Acid ◽  
Endogenous Pyrogen ◽  
Intracisternal Injection ◽  
Bacterial Peptidoglycan ◽  
Pyrogenic Activity

Fever can be elicited in the rabbit by the intravenous administration of relatively large doses of a synthetic immunoadjuvant, N-acetylmuramyl-L-alanyl-D-isoglutamine, or muramyl dipeptide (MDP). This response could be mediated by endogenous pyrogen because MDP has been shown to induce their production both in vivo and in vitro. The results reported here show that intracisternal injection of minute amounts of MDP could elevate fever without activating the release of endogenous pyrogen in the plasma or in the cerebrospinal fluid. Moreover, indomethacin inhibited hyperthermia produced by intracerebroventricular administration of MDP. Therefore, our findings argue in favor of a direct effect of the glycopeptide on the thermoregulatory centers besides its indirect effect through the production of leukocytic pyrogen. This molecule apparently represents the minimal requirement for the pyrogenicity of bacterial peptidoglycan because administration, even by the intracerebral route, of a mixture of muramic acid and of its dipeptide moiety did not elicit fever.

A new method to measure amino sugar isomers and amino acids in soil extracts and soil hydrolysates based on AccQ.Tag-chemistry and reversed phase ultra-high-performance liquid chromatography

2020 ◽  
Author(s):  
Erika Salas ◽  
Alexander König ◽  
Christina Kaiser ◽  
Wolfgang Wanek
Keyword(s):  
Amino Acids ◽  
High Performance Liquid Chromatography ◽  
High Performance ◽  
Amino Sugar ◽  
Reversed Phase ◽  
Amino Sugars ◽  
Muramic Acid ◽  
Soil Extracts ◽  
Soil Microbial ◽  
Bacterial Peptidoglycan

<p>Soil microbial necromass represents a significant proportion (>50%) of soil organic matter (SOM). Microbial necromass consists mainly of particulate organic residues from fragmented cells walls and other slow turnover cytoplasmic components of dead fungi and bacteria. Some of the key components of microbial cell walls, such as peptides and amino sugar polymers, can remain and accumulate in the soil over prolonged times. Amino sugars have been used as biomarkers to quantify the contribution of microbial necromass to stabilized SOM. The different amino sugars present in polymeric form in soils can be released by acid hydrolysis and allow the estimation of the contribution of both fungal and bacterial necromass to the SOM pool. Among the amino sugars, hexosamine isomers (glucosamine, galactosamine, mannosamine) and muramic acid (the ether of lactic acid and glucosamine) are the most abundant ones. Muramic acid is specific to bacterial peptidoglycan while glucosamine is an abundant cell wall component of both, fungal chitin and bacterial peptidoglycan.</p><p>There are several chromatographic methods to measure free and bound amino sugars and amino acids in soil extracts and soil hydrolysates, but none of them allow the combined determination of amino sugar biomarkers and amino acids simultaneously in a single assay for rapid analysis. This is important as a large fraction of soil necromass N (>50%) consists of non-amino sugar-N, such as proteins and nucleic acids. In this study we therefore adopt a method based on 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AccQ.Tag) derivatization of amino compounds and optimized chromatographic (reversed phase) separation to simultaneously measure amino sugars (isomers) and amino acids in soil extracts and soil hydrolysates using ultra-high-performance liquid chromatography coupled to fluorescence or UV detection.</p><p>The use of this method allows for fast, robust and highly sensitive quantification of amino acids and amino sugars in environmental samples at sub-micromolar levels. This approach will help to improve our understanding of soil microbial necromass dynamics and their inherent effect on soil C and N sequestration. The AccQ.Tag chemistry also allows compound detection by electrospray ionization (ESI)-mass spectrometry, enabling isotope (<sup>13</sup>C, <sup>15</sup>N) tracing applications.</p>

Bacterial Peptidoglycan Stapling with Functionalized D-Amino Acids

2019 ◽  
Author(s):  
Sylvia L. Rivera ◽  
Akbar Espaillat ◽  
Arjun K. Aditham ◽  
Peyton Shieh ◽  
Chris Muriel-Mundo ◽  
...  
Keyword(s):  
Cell Wall ◽  
Clinical Success ◽  
Bacterial Species ◽  
Enzymatic Reaction ◽  
Amino Acid Derivative ◽  
Wall Structure ◽  
Live Bacteria ◽  
Cross Links ◽  
Osmotic Lysis ◽  
Bacterial Peptidoglycan

Transpeptidation reinforces the structure of cell wall peptidoglycan, an extracellular heteropolymer that protects bacteria from osmotic lysis. The clinical success of transpeptidase-inhibiting β-lactam antibiotics illustrates the essentiality of these cross-linkages for cell wall integrity, but the presence of multiple, seemingly redundant transpeptidases in many bacterial species makes it challenging to determine cross-link function precisely. Here we present a technique to covalently link peptide strands by chemical rather than enzymatic reaction. We employ bio-compatible click chemistry to induce triazole formation between azido- and alkynyl-D-alanine residues that are metabolically installed in the cell walls of Gram-positive and Gram-negative bacteria. Synthetic triazole cross-links can be visualized by substituting azido-D-alanine with azidocoumarin-D-alanine, an amino acid derivative that undergoes fluorescent enhancement upon reaction with terminal alkynes. Cell wall stapling protects the model bacterium Escherichia coli from β-lactam treatment. Chemical control of cell wall structure in live bacteria can provide functional insights that are orthogonal to those obtained by genetics.<br>

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