N-Acetylmuramic acid

{{short description|Chemical compound}}

{{distinguish|N-Acetylneuraminic acid}}

{{DISPLAYTITLE:N-Acetylmuramic acid}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 443215358

| Name=N-Acetylmuramic acid

| ImageFile = N-Acetylmuramic acid.svg

| ImageSize = 200 px

| IUPACName = N-Acetylmuramic acid

| SystematicName = (2R)-2-{[(2R,3R,4R,5R)-2-Acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxy}propanoic acid

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 10597-89-4

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 246FXU111L

| PubChem = 5462244

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4575341

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 21615

| SMILES = O=C(O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1NC(=O)C)CO)C

| InChI = 1/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1

| InChIKey = MNLRQHMNZILYPY-MKFCKLDKBR

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = MNLRQHMNZILYPY-MKFCKLDKSA-N

}}

|Section2={{Chembox Properties

| C=11 | H=19 | N=1 | O=8

| MolarMass =

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

N-Acetylmuramic acid (NAM or MurNAc) is an organic compound with the chemical formula {{chem|C|11|H|19|N|O|8}}. It is a monomer of peptidoglycan in most bacterial cell walls, which is built from alternating units of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid, cross-linked by oligopeptides at the lactic acid residue of MurNAc.