CAS 86559-73-1

α-D-Glucopyranose, 2-deoxy-2-[[(3R)-3-hydroxy-1-oxotetradecyl]amino]-, 1-(dihydrogen phosphate) 3-[(3R)-3-hydroxytetradecanoate]

Description:

α-D-Glucopyranose, 2-deoxy-2-[[(3R)-3-hydroxy-1-oxotetradecyl]amino]-, 1-(dihydrogen phosphate) 3-[(3R)-3-hydroxytetradecanoate] is a complex chemical compound characterized by its structural components, which include a glucopyranose sugar moiety, a long-chain fatty acid derivative, and phosphate groups. This compound features a deoxy modification at the second carbon of the glucopyranose ring, which alters its reactivity and biological interactions. The presence of a hydroxy group and an amide linkage contributes to its potential biological activity, possibly influencing membrane dynamics or cellular signaling pathways. The phosphate group suggests that this compound may play a role in energy transfer or signaling within biological systems. Its long hydrophobic fatty acid chain indicates that it may have amphiphilic properties, allowing it to interact with both aqueous and lipid environments. Overall, this compound's unique structure may confer specific biochemical functions, making it of interest in fields such as biochemistry, pharmacology, and materials science.

Formula: C₃₄H₆₆NO₁₂P

InChI: InChI=1/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26-,27-,28-,31-,32-,33-,34-/m1/s1

InChI key: InChIKey=HEHQDWUWJVPREQ-XQJZMFRCSA-N

SMILES: N(C(C[C@@H](CCCCCCCCCCC)O)=O)[C@@H]1[C@@H](OC(C[C@@H](CCCCCCCCCCC)O)=O)[C@H](O)[C@@H](CO)O[C@@H]1OP(=O)(O)O

Synonyms:

• α-D-Glucopyranose, 2-deoxy-2-[[(3R)-3-hydroxy-1-oxotetradecyl]amino]-, 1-(dihydrogen phosphate) 3-[(3R)-3-hydroxytetradecanoate]
• α-D-Glucopyranose, 2-deoxy-2-[(3-hydroxy-1-oxotetradecyl)amino]-, 1-(dihydrogen phosphate) 3-(3-hydroxytetradecanoate), [2(R),3(R)]-
• lipid X
• Phosphoric acid dihydrogen [2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-α-D-glucopyranosyl] ester
• 2,3-Di(3-hydroxymyristoyl)glucosamine 1-phosphate
• 2-[[(3R)-3-Hydroxymyristoyl]amino]-2-deoxy-3-O-[(3R)-3-hydroxymyristoyl]α-D-glucopyranose 1-phosphoric acid
• N,3-O-Bis[(R)-3-hydroxytetradecanoyl]-α-D-glucosamine 1-phosphoric acid
• Compound 401

Lipid X

CAS: 86559-73-1

Lipid X is a monosaccharide precursor of E coli lipid A.

Formula: C₃₄H₆₆NO₁₂P

Color and Shape: Solid

Molecular weight: 711.86

Ref: TM-T32778

Lipid X

CAS: 86559-73-1

Lipid X is a monosaccharide precursor of E. coli lipid A. It is an N-acyl-D-glucosamine 1-phosphate where the N-acyl group is (R)-3-hydroxytetradecanoyl and carrying an additional (R)-3-hydroxytetradecanoyl, and it is a component of the cell wall of Gram-negative bacteria. Due to its physiological functions and biological properties, Lipid X can be used to treat infectious diseases, autoimmune diseases, and HIV infection. It has also been shown to inhibit the production of inflammatory cytokines such as tumor necrosis factor alpha (TNF-α) and interleukin-1β (IL-1β). This effect is due to its ability to disrupt hydrogen bonds between lipids in the cell membrane. As a biosynthetic intermediate of Lipid A, it seems to play a role in bacterial virulence and can trigger an immune response in humans, and protect against endotoxins.

Formula: C₃₄H₆₆NO₁₂P

Purity: Min. 95%

Molecular weight: 711.86 g/mol

Ref: 3D-ML76134

Lipid X

Controlled Product

CAS: 86559-73-1

Formula: C₃₄H₆₆NO₁₂P

Color and Shape: Neat

Molecular weight: 711.861

Ref: TR-L468735