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Pam3CSK4

Pam3CSK4 is a toll-like receptor 1/2 (TLR1/2) agonist with an EC50 of 0.47 ng/mL for human TLR1/2

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CAT No: P4102

CAS No: 112208-00-1

Synonyms/Alias: Pam3CSK4;112208-00-1;(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(hexadecanoylamino)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoic acid;Pam3Cys-Ser-(Lys)4;N-Palmitoyl-5,6-dipalmitoylcysteinyl-seryl-lysine(4);Pam3CSK4 TFA;P3C-SK4;P3CSK4;Pam(3)-Cys-Ser-(Lys)4;Pam(3)-Cys-Ser-Lys(4);SCHEMBL183536;CHEMBL506348;SCHEMBL25219115;AKOS024458265;AT35618;FP109571;(2S)-6-AMINO-2-[(2S)-6-AMINO-2-[(2S)-6-AMINO-2-[(2S)-6-AMINO-2-[(2S)-2-[(2R)-3-{[2,3-BIS(HEXADECANOYLOXY)PROPYL]SULFANYL}-2-HEXADECANAMIDOPROPANAMIDO]-3-HYDROXYPROPANAMIDO]HEXANAMIDO]HEXANAMIDO]HEXANAMIDO]HEXANOIC ACID;(N-palmitoyl-S-[2,3-bis(palmitoyloxy)-(2rs)-propyl]-[r]-cysteinyl-[s]-seryl-[s]-lysyl-[s]-lysyl-[s]-lysyl-[s]-lysine);L-Lysine, N2-(N2-(N2-(N2-(N-(S-(2,3-bis((1-oxohexadecyl)oxy)propyl)-N-(1-oxohexadecyl)-L-cysteinyl)-L-seryl)-L-lysyl)-L-lysyl)-L-lysyl)-;Palmitoyl-Cys((RS)-2,3-di(palmitoyloxy)-propyl)-Ser-Lys-Lys-Lys-Lys-OH trifluoroacetate salt;

Chemical Name: (2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(hexadecanoylamino)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoic acid

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC81H156N10O13S
M.W/Mr.1510.2
SequenceOne Letter Code:XSKKKK
Biological ActivityTLR1/TLR2 agonist. Synthetic analog of the triacylated N-terminal part of bacterial lipoproteins. Potent adjuvant in vivo. Potent activator of Balb/c splenocytes.
InChIInChI=1S/C81H156N10O13S/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-55-73(93)86-72(65-105-64-66(104-75(95)57-42-39-36-33-30-27-24-21-18-15-12-9-6-3)63-103-74(94)56-41-38-35-32-29-26-23-20-17-14-11-8-5-2)80(100)91-71(62-92)79(99)89-68(52-44-48-59-83)77(97)87-67(51-43-47-58-82)76(96)88-69(53-45-49-60-84)78(98)90-70(81(101)102)54-46-50-61-85/h66-72,92H,4-65,82-85H2,1-3H3,(H,86,93)(H,87,97)(H,88,96)(H,89,99)(H,90,98)(H,91,100)(H,101,102)/t66?,67-,68-,69-,70-,71-,72-/m0/s1
InChI KeyOEDPHAKKZGDBEV-GFPBKZJXSA-N
Canonical SMILESCCCCCCCCCCCCCCCC(=O)NC(CSCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)O
Isomeric SMILESCCCCCCCCCCCCCCCC(=O)N[C@@H](CSCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)O
References1. Irvine KL, et al. The molecular basis for recognition of bacterial ligands at equine TLR2, TLR1 and TLR6. Vet Res. 2013 Jul 4;44:50.
2. Chen Y, et al. TLR2 agonist Pam3CSK4 enhances the antibacterial functions of GM-CSF induced neutrophils to methicillin-resistant Staphylococcus aureus. Microb Pathog. 2019 May;130:204-212.
3. Du X, et al. Systemic stimulation of TLR2 impairs neonatal mouse brain development. PLoS One. 2011 May 6;6(5):e19583.

1. Low bone turnover and low BMD in Down syndrome: effect of intermittent PTH treatment

2. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function

3. Cationic cell-penetrating peptides are potent furin inhibitors

4. Constitutive and inflammation-dependent antimicrobial peptides produced by epithelium are differentially processed and inactivated by the commensal Finegoldia magna and the pathogen Streptococcus pyogenes

5. Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line

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