Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H19NO8 |
| Molecular Weight | 293.2705 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H](O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O)[C@@H]1NC(C)=O)C(O)=O
InChI
InChIKey=MNLRQHMNZILYPY-MDMHTWEWSA-N
InChI=1S/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11+/m1/s1
| Molecular Formula | C11H19NO8 |
| Molecular Weight | 293.2705 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
N-acetylmuramic acid (MurNAc) is a bacterial cell wall component. Peptidoglycan, also called murein, is a polymer that consists of long glycan chains that are cross-linked via flexible peptide bridges to form a strong but elastic structure that protects the underlying protoplast from lysing due to the high internal osmotic pressure. The peptidoglycan is the only cell wall polymer common to both gram-negative and gram-positive bacteria. The glycan chain is built up of alternating, β-1,4-linked N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) subunits. The chemistry of the glycan chains varies only slightly between different bacteria.
Approval Year
Sample Use Guides
In Vitro Use Guide
Curator's Comment: THP-1 cells were co-treated with the LPS in the presence of N-acetylmuramic acid and N-acetylglucosamine, as components of PGN, and the competition binding assay to CD14 and LBP was performed. N-acetylmuramic acid inhibited the induction of inflammatory cytokine expression by LPS and the binding of LPS to CD14 or LBP whereas N-acetylglucosamine did not show such effect. Collectively, the results suggest that S. sanguinis PGN inhibited the cytokine expression induced by the LPS of periodontopathogens due to the inhibition of LPS binding to LBP and CD14. N-acetylmuramic acid of PGN may play a role in inhibition of the LPS binding of periodontopathogens to CD14 and LBP.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:00:37 GMT 2023
by
admin
on
Sat Dec 16 02:00:37 GMT 2023
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| Record UNII |
44N0ZKC921
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| Record Status |
Validated (UNII)
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| Record Version |
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6323218
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DTXSID70977230
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m7659
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44N0ZKC921
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61633-75-8
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admin on Sat Dec 16 02:00:37 GMT 2023 , Edited by admin on Sat Dec 16 02:00:37 GMT 2023
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