N-乙酰胞壁酸, N-Acetylmuramic acid

N-Acetylmuramic acid (MurNAc) is a component of the glycan strands in bacterial peptidoglycan. It is linked to N-acetylglucosamine (GlcNAc) by β-1,4 linkages in an alternating pattern, as well as to the peptide side chains via its lactyl side chain, in native peptidoglycan.

Aldehydo-N-acetylmuramic acid is a N-acetylmuramic acid. It derives from an aldehydo-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.