Monophosphoryl 3-deacyl Lipid A ammonium salt

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Category	Adjuvants
Catalog NO.	BPG-3013
Product Name	Monophosphoryl 3-deacyl Lipid A ammonium salt
CAS	1699735-79-9
Molecular Formula	C82H158N3O20P
Molecular Weight	1537.11

Monophosphoryl 3-deacyl Lipid A ammonium salt

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Product Information

Description	Monophosphoryl 3-deacyl Lipid A ammonium salt is a remarkable biomedical innovation, aiding in studying infectious diseases. As an exquisitely crafted immunostimulating adjuvant, it is widely used for developing vaccines.
Synonyms	3D-PHAD^®
IUPAC Name	azanium;[(2R,3S,4R,5R,6R)-5-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]-2-(hydroxymethyl)-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxy-6-[[(2R,3S,4R,5R,6S)-3,4,6-trihydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]oxan-2-yl]methoxy]oxan-3-yl] hydrogen phosphate
Canonical SMILES	CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(C(OC(C1OP(=O)(O)[O-])CO)OCC2C(C(C(C(O2)O)NC(=O)CC(CCCCCCCCCCC)O)O)O)NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC.[NH4+]
InChI	InChI=1S/C82H155N2O20P.H3N/c1-6-11-16-21-26-31-33-38-43-48-53-58-72(89)99-66(56-51-46-41-36-29-24-19-14-9-4)61-71(88)84-76-80(103-74(91)62-67(57-52-47-42-37-30-25-20-15-10-5)100-73(90)59-54-49-44-39-34-32-27-22-17-12-7-2)79(104-105(95,96)97)68(63-85)102-82(76)98-64-69-77(92)78(93)75(81(94)101-69)83-70(87)60-65(86)55-50-45-40-35-28-23-18-13-8-3;/h65-69,75-82,85-86,92-94H,6-64H2,1-5H3,(H,83,87)(H,84,88)(H2,95,96,97);1H3/t65-,66-,67-,68-,69-,75-,76-,77-,78-,79-,80-,81+,82-;/m1./s1
InChIKey	XERJCJBCCDONJL-WOBTUNBLSA-N
Purity	>99%
Related CAS	1465797-24-3 (free acid)
Appearance	Powder
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	1536.118
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 64.07%, H 10.36%, N 2.73%, O 20.82%, P 2.02%

References

1. Singh P, Matyas GR, Anderson A, Beck Z. Biophysical characterization of polydisperse liposomal adjuvant formulations. Biochem Biophys Res Commun. 2020 Aug 20;529(2):362-365. doi: 10.1016/j.bbrc.2020.05.156. Epub 2020 Jul 1. PMID: 32703436. PubMed ID: 32703436.
2. Martin ML, Bitzer AA, Schrader A, Bergmann-Leitner ES, Soto K, Zou X, Beck Z, Matyas GR, Dutta S. Comparison of immunogenicity and safety outcomes of a malaria vaccine FMP013/ALFQ in rhesus macaques (Macaca mulatta) of Indian and Chinese origin. Malar J. 2019 Nov 27;18(1):377. doi: 10.1186/s12936-019-3014-5. PubMed ID: 31775762.
3. Hernandez A, Luan L, Stothers CL, Patil NK, Fults JB, Fensterheim BA, Guo Y, Wang J, Sherwood ER, Bohannon JK. Phosphorylated Hexa-Acyl Disaccharides Augment Host Resistance Against Common Nosocomial Pathogens. Crit Care Med. 2019 Nov;47(11):e930-e938. doi: 10.1097/CCM.0000000000003967. PubMed ID: 31567352.
4. Beugeling M, De Zee J, Woerdenbag HJ, Frijlink HW, Wilschut JC, Hinrichs WLJ. Respiratory syncytial virus subunit vaccines based on the viral envelope glycoproteins intended for pregnant women and the elderly. Expert Rev Vaccines. 2019 Sep;18(9):935-950. doi: 10.1080/14760584.2019.1657013. Epub 2019 Aug 25. PubMed ID: 31446807.
5. Singh P, Bodycomb J, Travers B, Tatarkiewicz K, Travers S, Matyas GR, Beck Z. Particle size analyses of polydisperse liposome formulations with a novel multispectral advanced nanoparticle tracking technology. Int J Pharm. 2019 Jul 20;566:680-686. doi: 10.1016/j.ijpharm.2019.06.013. Epub 2019 Jun 6. PubMed ID: 31176851.
6. Smith RJ, Bryant RG. Metal substitutions incarbonic anhydrase: a halide ion probe study. Biochem Biophys Res Commun. 1975 Oct 27;66(4):1281-6. PubMed ID: 31043512.
7. Cawlfield A, Genito CJ, Beck Z, Bergmann-Leitner ES, Bitzer AA, Soto K, Zou X, Hadiwidjojo SH, Gerbasi RV, Mullins AB, Noe A, Waters NC, Alving CR, Matyas GR, Dutta S. Safety, toxicity and immunogenicity of a malaria vaccine based on the circumsporozoite protein (FMP013) with the adjuvant army liposome formulation containing QS21 (ALFQ). Vaccine. 2019 Jun 27;37(29):3793-3803. doi: 10.1016/j.vaccine.2019.05.059. Epub 2019 May 28. PubMed ID: 31151801.
8. Taleghani N, Bozorg A, Azimi A, Zamani H. Immunogenicity of HPV and HBV vaccines: adjuvanticity of synthetic analogs of monophosphoryl lipid A combined with aluminum hydroxide. APMIS. 2019 Mar;127(3):150-157. doi: 10.1111/apm.12927. PubMed ID: 30746792.

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