Muramyl dipeptide

Muramyl dipeptide
IUPAC name (4R)-4-[ [(2S)-2-[ [(2R)-2-[(2R,5S)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
Other names Acetylmuramyl-Alanyl-Isoglutamine
Identifiers
CAS number	53678-77-6
PubChem	11620162
ChemSpider	9794910 Y
MeSH	Muramyl+dipeptide
Jmol-3D images	Image 1
SMILES O=C(N)[C@H](NC(=O)[C@@H](NC(=O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1NC(=O)C)CO)C)C)CCC(=O)O
InChI InChI=1S/C19H32N4O11/c1-7(17(30)23-10(16(20)29)4-5-12(26)27)21-18(31)8(2)33-15-13(22-9(3)25)19(32)34-11(6-24)14(15)28/h7-8,10-11,13-15,19,24,28,32H,4-6H2,1-3H3,(H2,20,29)(H,21,31)(H,22,25)(H,23,30)(H,26,27)/t7-,8+,10+,11+,13+,14+,15+,19?/m0/s1 Y Key: BSOQXXWZTUDTEL-QAQREVAFSA-N Y InChI=1/C19H32N4O11/c1-7(17(30)23-10(16(20)29)4-5-12(26)27)21-18(31)8(2)33-15-13(22-9(3)25)19(32)34-11(6-24)14(15)28/h7-8,10-11,13-15,19,24,28,32H,4-6H2,1-3H3,(H2,20,29)(H,21,31)(H,22,25)(H,23,30)(H,26,27)/t7-,8+,10+,11+,13+,14+,15+,19?/m0/s1 Key: BSOQXXWZTUDTEL-QAQREVAFBN
Properties
Molecular formula	C19H32N4O11
Molar mass	492.47758
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Muramyl dipeptide is a peptidoglycan constituent of both Gram positive and Gram negative bacteria. It is composed of N-acetylmuramic acid linked by its lactic acid moiety to the N-terminus of an L-alanine D-isoglutamine dipeptide.^[1]

See also

• Dipeptide
• Mifamurtide, a synthetic analogue for the treatment of osteosarcoma

References

1. ^ Inohara, N.; Ogura, Y.; Fontalba, A.; Gutierrez, O.; Pons, F.; Crespo, J.; Fukase, K.; Inamura, S. et al. (2003). "Host Recognition of Bacterial Muramyl Dipeptide Mediated through NOD2. Implications for Crohn's Disease". Journal of Biological Chemistry 278 (8): 5509. doi:10.1074/jbc.C200673200. PMID 12514169.  edit

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