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Atomfair 6-O-Stearoyl-N-acetylmuramyl-alanylisoglutamine 6-SMDP, L18-MDP(ala) C37H66N4O12

Description 6-O-Stearoyl-N-acetylmuramyl-alanylisoglutamine (CAS No. 62150-45-2) is a synthetic muramyl dipeptide (MDP) derivative with the molecular formula C37H66N4O12. This high-purity compound features a stearoyl (C18) fatty acid chain esterified at the 6-O position of the N-acetylmuramyl backbone, conjugated with alanyl-isoglutamine. It is widely utilized in immunological research as a potent immunostimulant and adjuvant due to its structural similarity to bacterial cell wall components. The IUPAC name, (2R)-2-[[(2S)-2-[2-[(2S,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(octadecanoyloxymethyl)oxan-4-yl]oxypropanoylamino]propanoyl]amino]-5-amino-5-oxopentanoic acid , reflects its complex peptidoglycan-like architecture. Suitable for in vitro and in vivo studies, this product is provided as a lyophilized powder with ??95% purity (HPLC). Store at -20??C protected from moisture.

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Description

Description

6-O-Stearoyl-N-acetylmuramyl-alanylisoglutamine (CAS No. 62150-45-2) is a synthetic muramyl dipeptide (MDP) derivative with the molecular formula C37H66N4O12. This high-purity compound features a stearoyl (C18) fatty acid chain esterified at the 6-O position of the N-acetylmuramyl backbone, conjugated with alanyl-isoglutamine. It is widely utilized in immunological research as a potent immunostimulant and adjuvant due to its structural similarity to bacterial cell wall components. The IUPAC name, (2R)-2-[[(2S)-2-[2-[(2S,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(octadecanoyloxymethyl)oxan-4-yl]oxypropanoylamino]propanoyl]amino]-5-amino-5-oxopentanoic acid, reflects its complex peptidoglycan-like architecture. Suitable for in vitro and in vivo studies, this product is provided as a lyophilized powder with ??95% purity (HPLC). Store at -20??C protected from moisture.

  • CAS No: 62150-45-2
  • Molecular Formula: C37H66N4O12
  • Molecular Weight: 758.9
  • Exact Mass: 758.46772355
  • Monoisotopic Mass: 758.46772355
  • IUPAC Name: (2R)-2-[[(2S)-2-[2-[(2S,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(octadecanoyloxymethyl)oxan-4-yl]oxypropanoylamino]propanoyl]amino]-5-amino-5-oxopentanoic acid
  • SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)NC(=O)C)OC(C)C(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)N)C(=O)O)O
  • Synonyms: 6-Smdp, L18-Mdp(ala), 6-O-Stearoyl-muramyl dipeptide, 6-O-Stearoyl-N-acetylmuramyl-alanylisoglutamine, 6-O-Stearoyl-N-acmu-ala-iso-gln

Application

6-O-Stearoyl-N-acetylmuramyl-alanylisoglutamine is a key tool for studying innate immune responses via NOD2 receptor activation. Researchers employ it as a synthetic analog of bacterial peptidoglycan to investigate macrophage activation, cytokine production, and vaccine adjuvant mechanisms. Its lipophilic stearoyl modification enhances cellular uptake and bioactivity compared to unmodified MDP. Applications include experimental models of autoimmune diseases, infectious immunity, and cancer immunotherapy development.

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