Muramic Acid
Title: Muramic Acid
CAS Registry Number: 1114-41-6
Additional Names: (R)-2-Amino-3-O-(1-carboxyethyl)-2-deoxy-D-glucose; 3-O-a-carboxyethyl-D-glucosamine
Molecular Formula: C9H17NO7
Molecular Weight: 251.23
Percent Composition: C 43.03%, H 6.82%, N 5.58%, O 44.58%
Literature References: Amino sugar found (as the N-acetyl derivative) in peptidoglycan, the main skeletal component of the bacterial cell wall. Discovery: J. T. Park, J. Biol. Chem. 194, 885 (1952). Isoln from spores of Bacillus megatherium: R. E. Strange, F. A. Dark, Nature 177, 186 (1956). Identification and synthesis: R. E. Strange, L. H. Kent, Biochem. J. 71, 333 (1959). Stereospecific synthesis: Y. Matsushima, J. T. Park, J. Org. Chem. 27, 3581 (1962); eidem, Biochem. Prep. 10, 109 (1963); T. Osawa, R. W. Jeanloz, J. Org. Chem. 30, 448 (1965). Review of peptidoglycan structure: H. J. Rogers, Ann. N.Y. Acad. Sci. 235, 29-51 (1974). Use to determine bacterial levels in mammalian tissues: J. Gilbart et al., J. Microbiol. Methods 5, 271 (1986); in airborne dust: A. Fox et al., Appl. Environ. Microbiol. 59, 4354 (1993).
Properties: Crystals from water, mp 152-154° (dec); [a]D25 +103° (c = 0.26 in water) (Matsushima, Park). Also reported as crystals from 90% ethanol, mp 160-162° (dec); [a]D22 +146° (6 minutes) ® +116° (31 hrs) (c = 0.57 in water) (Osawa, Jeanloz).
Melting point: mp 152-154° (dec); mp 160-162° (dec)
Optical Rotation: [a]D25 +103° (c = 0.26 in water) (Matsushima, Park); [a]D22 +146° (6 minutes) ® +116° (31 hrs) (c = 0.57 in water) (Osawa, Jeanloz)
 
Derivative Type: N-Acetylmuramic acid
CAS Registry Number: 10597-89-4
CAS Name: (R)-2-(Acetylamino)-3-O-(1-carboxyethyl)-2-deoxy-D-glucose
Molecular Formula: C11H19NO8
Molecular Weight: 293.27
Percent Composition: C 45.05%, H 6.53%, N 4.78%, O 43.64%
Properties: Crystals from ethyl acetate + methanol, mp 119-121°. [a]D20 +56° (10 minutes) ® +40° (24 hrs) (c = 0.68 in water).
Melting point: mp 119-121°
Optical Rotation: [a]D20 +56° (10 minutes) ® +40° (24 hrs) (c = 0.68 in water)
 
Use: As chemical marker for the detection of bacterial contamination.

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