Kdo2-Lipid A (KLA)

• CAT Number: I030023
• CAS Number: 1246298-62-3
• Molecular Formula: C110H214N6O39P2
• Molecular Weight: 2306.87
• Purity: 98%
• Synonyms: Kdo2-Lipid A (KLA); Di[3-deoxy-D-manno-octulosonyl]-lipid A (ammonium salt)
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: ammonium (2R,4R,6R)-2-(((2R,4R,5R,6R)-2-carboxylato-6-((R)-1,2-dihydroxyethyl)-2-(((2R,3S,4R,5R,6R)-5-((R)-3-(dodecanoyloxy)tetradecanamido)-6-(((2R,3S,4R,5R,6R)-3-hydroxy-6-((hydroxyoxidophosphoryl)oxy)-5-((R)-3-hydroxytetradecanamido)-4-(((R)-3-hydroxytetradecanoyl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)-3-((hydroxyoxidophosphoryl)oxy)-4-(((R)-3-(tetradecanoyloxy)tetradecanoyl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)-5-hydroxytetrahydro-2H-pyran-4-yl)oxy)-6-((R)-1,2-dihydroxyethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-carboxylate
• InChI: InChI=1S/C110H202N2O39P2.4H3N/c1-7-13-19-25-31-37-38-44-50-56-62-68-92(123)142-82(66-60-54-48-42-35-29-23-17-11-5)72-94(125)146-104-96(112-90(121)71-81(65-59-53-47-41-34-28-22-16-10-4)141-91(122)67-61-55-49-43-36-30-24-18-12-6)105(144-88(102(104)150-152(133,134)135)78-140-109(107(129)130)74-86(98(127)101(148-109)85(119)76-114)147-110(108(131)132)73-83(117)97(126)100(149-110)84(118)75-113)139-77-87-99(128)103(145-93(124)70-80(116)64-58-52-46-40-33-27-21-15-9-3)95(106(143-87)151-153(136,137)138)111-89(120)69-79(115)63-57-51-45-39-32-26-20-14-8-2;;;;/h79-88,95-106,113-119,126-128H,7-78H2,1-6H3,(H,111,120)(H,112,121)(H,129,130)(H,131,132)(H2,133,134,135)(H2,136,137,138);4*1H3/t79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,95-,96-,97?,98-,99-,100-,101-,102-,103-,104-,105-,106-,109-,110-;;;;/m1..../s1
• InChIKey: HBSUHPVFGADBOQ-IIEJLJSISA-N
• SMILES: O[C@H]([C@@H](CO[C@@H]([C@@H]1NC(C[C@H](OC(CCCCCCCCCCC)=O)CCCCCCCCCCC)=O)O[C@H](CO[C@]2(C([O-])=O)C[C@@H](O[C@@]3(C([O-])=O)O[C@H]([C@H](O)CO)C(O)[C@H](O)C3)[C@@H](O)[C@@H]([C@H](O)CO)O2)[C@@H](OP([O-])(O)=O)[C@@H]1OC(C[C@H](OC(CCCCCCCCCCCCC)=O)CCCCCCCCCCC)=O)O[C@H](OP(O)([O-])=O)[C@@H]4NC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H]4OC(C[C@H](O)CCCCCCCCCCC)=O.[NH4+].[NH4+].[NH4+].[NH4+]

Kdo2-Lipid A (KLA) (Cat.No:I030023) is a nearly homogeneous Re lipopolysaccharide (LPS) substructure with endotoxin activity equal to that of native LPS. KLA is comparable to LPS and its activity is reduced by >103 in cells from TLR-4 deficient mice. The advantage of KLA over LPS is that it is a reproducible, defined natural product, and it can be detected by ESI/MS at the low concentrations used to stimulate animal cells. The purity of KLA should also facilitate the structural analysis of its complexes with signaling receptors, such as TLR-4/MD2.

Reference

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