Muramic acid, 胞壁酸

Muramic acid hydrate

Muramic acid hydrate is a methylated, fluorinated glycosidic compound. It is a complex carbohydrate that is structurally related to the monosaccharide D-glucuronic acid. Muramic acid hydrate has been modified by the addition of an oligosaccharide and polysaccharide chain at its termini. The modification increases its stability in water, making it suitable for use as a sugar substitute. This product has been synthesized from D-glucose by an enzymatic process with high purity and high quality.

Amino sugar found (as the N-acetyl derivative) in peptidoglycan, the main skeletal component of the bacterial cell wall of Gram negative and Gram positive bacteria. Used as a chemical marker for the detection of bacterial contamination.

Muramic acid is a marker for Gram-positive bacteria.

Muramic acid, also known as muramate or murexide, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Muramic acid exists as a solid, soluble (in water), and a weakly acidic compound (based on its pKa). Muramic acid has been found in human spleen tissue. Within the cell, muramic acid is primarily located in the cytoplasm.

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.

COA:

Product name: Muramic acid，2-Amino-3-O-(1-carboxyethyl)-2-deoxy-D-glucose

CAS: 1114-41-6           M.F.: C₉H₁₇NO₇                  M.W.: 251.23