Muramic acid

Muramic acid
Names
Preferred IUPAC name
2-[3-Amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoic acid
Systematic IUPAC name
2-{[3-Amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
Identifiers
3DMet B05203
2334586
1114-41-6 
40525-29-9 Yes
ChEBI CHEBI:7027 
ChemSpider 7992151 α-muramic acid 
389857 muramic acid (mixture of anomers) 
394190 β-muramic acid Yes
EC number 214-214-9
Jmol-3D images Image
KEGG C06470 
PubChem 441038 (2R),(3R,4R,5S,6R)
12313001 (),(3R,4R,5S,6R)
44123550 (2R),(2R,4R,6R)
45039974 (2R),()
433580
Properties
C9H17NO7
Molar mass 251.23378
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
  verify (what is: Yes/?)
Infobox references

Muramic acid is an amino sugar acid. In terms of chemical composition, it is the ether of lactic acid and glucosamine. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls.[1] The bacteria Chlamydiae are unusual for not having muramic acid in their cell walls.[2]

References

  1. Muramic acid - Compound Summary, PubChem.
  2. Barbour, A G; Amano, K; Hackstadt, T; Perry, L; Caldwell, H D (July 1982). "Chlamydia trachomatis has penicillin-binding proteins but not detectable muramic acid.". Journal of Bacteriology 151 (1): 420–8. PMID 7085567. Retrieved 13 December 2014.