10597-89-4, N-乙酰胞壁酸, N-Acetylmuramic acid, MurNAc, CAS:10597-89-4

10597-89-4, N-乙酰胞壁酸,
N-Acetylmuramic acid,
CAS:10597-89-4
C11H19NO8 / 293.27
MFCD00221511

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.

CAS Number	10597-89-4
Product Name	(R)-2-Acetamido-3-O-(1-carboxyethyl)-2-deoxy-D-glucose
IUPAC Name	(2R)-2-[(2R,3R,4R,5R)-2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxypropanoic acid
Molecular Formula	C11H19NO8
Molecular Weight	293.27 g/mol
InChI	InChI=1S/C11H19NO8/c1-5(11(18)19)20-10(9(17)8(16)4-14)7(3-13)12-6(2)15/h3,5,7-10,14,16-17H,4H2,1-2H3,(H,12,15)(H,18,19)/t5-,7+,8-,9-,10-/m1/s1
InChI Key	SOARVSUSWULNDI-TVVSKHENSA-N
SMILES	CC(C(=O)O)OC(C(C=O)NC(=O)C)C(C(CO)O)O
Synonyms	2-acetamido-3-O-((S)-1-carboxyethyl)-2-deoxy-D-glucose, 2-acetamido-4-O-(1-carboxyethyl)-2-deoxyglucose, 2-acetamido-4-O-(1-carboxyethyl)-2-deoxyglucose, (beta-D)-isomer, 4-O-NAcMur, acetylmuramic acid, N-acetylisomuramic acid, N-acetylmuramic acid
Canonical SMILES	CC(C(=O)O)OC(C(C=O)NC(=O)C)C(C(CO)O)O
Isomeric SMILES	C[C@H](C(=O)O)O[C@H]([C@H](C=O)NC(=O)C)[C@@H]([C@@H](CO)O)O

CAS No: 10597-89-4 Synonyms: 2-Acetamido-2-deoxy-3-O-(D-1-carboxyethyl)-D-glucopyranoseMurNAcNAMA MDL No: MFCD00221511 Chemical Formula: C11H19NO8 Molecular Weight: 293.27

References: 1. Herbold DR, Glasser L, JBC 1975, 250, 5, p16762. Nathan S, Osawa T, Flowers HM, et al., J. Biol. Chem. 1966

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