Monophosphoryl Lipid A

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Category	Adjuvants
Catalog NO.	BPG-3010
Product Name	Monophosphoryl Lipid A
CAS	1246298-63-4
Molecular Formula	C96H184N3O22P
Molecular Weight	1763.47

Scheme Design
Custom Synthesis
cGMP Manufacturing
Quality Assurance

Product Information
References
Documents
Reviews

Product Information

Description	Monophosphoryl Lipid A is a toll-like receptor 4 agonist with potential immunostimulatory activity, which is commonly used as a vaccine adjuvant.
Synonyms	MPLA (PHAD^®); phosphorylated hexaacyl disaccharide; Glycopyranoside Lipid A
IUPAC Name	azanium;[(2R,3S,4R,5R,6R)-6-[[(2R,3S,4R,5R,6S)-3,6-dihydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxyoxan-2-yl]methoxy]-2-(hydroxymethyl)-5-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-3-yl] hydrogen phosphate
Canonical SMILES	CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)NC1C(C(C(OC1OCC2C(C(C(C(O2)O)NC(=O)CC(CCCCCCCCCCC)O)OC(=O)CC(CCCCCCCCCCC)O)O)CO)OP(=O)(O)O)OC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC.N
InChI	InChI=1S/C96H181N2O22P.H3N/c1-7-13-19-25-31-37-39-45-51-57-63-69-85(104)114-79(67-61-55-49-43-35-29-23-17-11-5)73-84(103)98-90-94(119-88(107)74-80(68-62-56-50-44-36-30-24-18-12-6)115-86(105)70-64-58-52-46-40-38-32-26-20-14-8-2)92(120-121(110,111)112)81(75-99)117-96(90)113-76-82-91(108)93(118-87(106)72-78(101)66-60-54-48-42-34-28-22-16-10-4)89(95(109)116-82)97-83(102)71-77(100)65-59-53-47-41-33-27-21-15-9-3;/h77-82,89-96,99-101,108-109H,7-76H2,1-6H3,(H,97,102)(H,98,103)(H2,110,111,112);1H3/t77-,78-,79-,80-,81-,82-,89-,90-,91-,92-,93-,94-,95+,96-;/m1./s1
InChIKey	UPAZUDUZKTYFBG-HNPUZVNISA-N
Purity	> 99%
Appearance	Powder
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	1762.311
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 65.38%, H 10.52%, N 2.38% ,O 19.96%, P 1.76

References

1. Fisher BS, Dambrauskas N, Trakhimets O, Andrade DV, Smedley J, Sodora DL, Sather DN. Oral Immunization with HIV-1 Envelope SOSIP trimers elicits systemic immune responses and cross-reactive anti-V1V2 antibodies in non-human primates. PLoS One. 2020 May 29;15(5):e0233577. doi: 10.1371/journal.pone.0233577. PMID: 32470041; PMCID: PMC7259690. PubMed ID: 32470041.
2. Richard K, Perkins DJ, Harberts EM, Song Y, Gopalakrishnan A, Shirey KA, Lai W, Vlk A, Mahurkar A, Nallar S, Hawkins LD, Ernst RK, Vogel SN. Dissociation of TRIF bias and adjuvanticity. Vaccine. 2020 Jun 2;38(27):4298-4308. doi: 10.1016/j.vaccine.2020.04.042. Epub 2020 May 7. PMID: 32389496; PMCID: PMC7302928. PubMed ID: 32389496.
3. Boudousquié C, Boand V, Lingre E, Dutoit L, Balint K, Danilo M, Harari A, Gannon PO, Kandalaft LE. Development and Optimization of a GMP-Compliant Manufacturing Process for a Personalized Tumor Lysate Dendritic Cell Vaccine. Vaccines (Basel). 2020 Jan 14;8(1):E25. doi: 10.3390/vaccines8010025. PMID: 31947581. PubMed ID: 31947581.
4. Verma A, Schmidt BA, Elizaldi SR, Nguyen NK, Walter KA, Beck Z, Trinh HV, Dinsarapu AR, Lakshmanappa YS, Rane NN, Matyas GR, Rao M, Shen X, Tomaras GD, LaBranche CC, Reimann KA, Foehl DH, Gach JS, Forthal DN, Kozlowski PA, Amara RR, Iyer SS. Impact of Th1 CD4 TFH skewing on Antibody Responses to an HIV-1 Vaccine in Rhesus Macaques. J Virol. 2019 Dec 11;JVI.01737-19. doi: 10.1128/JVI.01737-19. [Epub ahead of print]. PMID: 31827000. PubMed ID: 31827000.
5. Wang L, Wang Z, Qin Y, Liang W. Delivered antigen peptides to resident CD8α+ DCs in lymph node by micelle-based vaccine augment antigen-specific CD8+ effector T cell response. Eur J Pharm Biopharm. 2020 Feb;147:76-86. doi: 10.1016/j.ejpb.2019.12.013. Epub 2019 Dec 28. PMID: 31887349. PubMed ID: 31887349.
6. 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.
7. Maynard S, Marshall JD, MacGill RS, Yu L, Cann JA, Cheng LI, McCarthy MP, Cayatte C, Robbins SH. Vaccination with synthetic long peptide formulated with CpG in an oil-in-water emulsion induces robust E7-specific CD8 T cell responses and TC-1 tumor eradication. BMC Cancer. 2019 Jun 6;19(1):540. doi: 10.1186/s12885-019-5725-y. PubMed ID: 31170937.
8. Belnoue E, Mayol JF, Carboni S, Di Berardino Besson W, Dupuychaffray E, Nelde A, Stevanovic S, Santiago-Raber ML, Walker PR, Derouazi M. Targeting self and neo-epitopes with a modular self-adjuvanting cancer vaccine. JCI Insight. 2019 Apr 23;5. pii: 127305. doi: 10.1172/jci.insight.127305. PubMed ID: 31013258.
9. Zhao Z, Hu Y, Harmon T, Pentel P, Ehrich M, Zhang C. Effect of Adjuvant Release Rate on the Immunogenicity of Nanoparticle-Based Vaccines: A Case Study with a Nanoparticle-Based Nicotine Vaccine. Mol Pharm. 2019 Jun 3;16(6):2766-2775. doi: 10.1021/acs.molpharmaceut.9b00279. Epub 2019 May 22. PubMed ID: 31075204.
10. Liang T, Leung LM, Opene B, Fondrie WE, Lee YI, Chandler CE, Yoon SH, Doi Y, Ernst RK, Goodlett DR. Rapid microbial identification and antibiotic resistance detection by mass spectrometric analysis of membrane lipids. Anal Chem. 2018 Dec 20. doi: 10.1021/acs.analchem.8b02611. [Epub ahead of print]...PubMed ID: 30571097.

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