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
CAS Number	1114-41-6 ;
3D model (JSmol)	Interactive image;
3DMet	L03117
Beilstein Reference	2334586
ChEBI	CHEBI:7027 ;
ChemSpider	7992151 α-muramic acid ; 389857 muramic acid (mixture of anomers) ; 394190 β-muramic acid ;
ECHA InfoCard	100.012.923
EC Number	214-214-9
KEGG	C06470 ;
PubChem CID	441038 (2R),(3R,4R,5S,6R); 12313001 (),(3R,4R,5S,6R); 44123550 (2R),(2R,4R,6R); 45039974 (2R),(); 433580;
UNII	D42T32747Z ;
	InChI InChI=1S/C9H17NO7/c1-3(8(13)14)16-7-5(10)9(15)17-4(2-11)6(7)12/h3-7,9,11-12,15H,2,10H2,1H3,(H,13,14)/t3-,4-,5-,6-,7-,9-/m1/s1 Key: MSFSPUZXLOGKHJ-KTZFPWNASA-N ;
	SMILES CC(OC1C(N)C(O)OC(CO)C1O)C(O)=O;
Properties
Chemical formula	C9H17NO7
Molar mass	251.23378
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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]

Chlamydia bacterial species notably lack muramic acid in their cell wall, thus do not gram stain.

References

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