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Pam3-Cys-OH

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Category
Other Unnatural Amino Acids
Catalog number
BAT-015835
CAS number
87420-41-5
Molecular Formula
C54H103NO7S
Molecular Weight
910.46
Pam3-Cys-OH
IUPAC Name
(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(hexadecanoylamino)propanoic acid
Synonyms
Palmitoyl-S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-L-cysteine; N-Palmitoyl-2,3-bis(palmitoyloxy)-2-propylcysteine; Palmitoyl-Cys((RS)-2,3-di(palmitoyloxy)-propyl)-OH
Density
0.966±0.06 g/cm3
Boiling Point
907.8±65.0 °C at 760 mmHg
Storage
Store at -20°C
InChI
InChI=1S/C54H103NO7S/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-51(56)55-50(54(59)60)48-63-47-49(62-53(58)45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)46-61-52(57)44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h49-50H,4-48H2,1-3H3,(H,55,56)(H,59,60)/t49?,50-/m0/s1
InChI Key
PZFZLRNAOHUQPH-GOOVXGPGSA-N
Canonical SMILES
CCCCCCCCCCCCCCCC(=O)NC(CSCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)O

Pam3-Cys-OH, a synthetic lipopeptide renowned for mimicking bacterial lipoproteins to elicit immune responses, finds diverse applications.

Vaccine Adjuvant: Pam3-Cys-OH acts as an adjuvant, bolstering the immune response by activating toll-like receptor 2 (TLR2). This activation not only enhances vaccine efficacy but also sustains robust immune responses crucial for combatting infectious diseases.

Immunotherapy Research: At the forefront of immunotherapy research, Pam3-Cys-OH sparks immune cell activation, particularly in macrophages and dendritic cells, leading to cytokine production and improved antigen presentation. By leveraging this activation, researchers delve into novel strategies for boosting immune responses against cancer and infectious diseases. Pam3-Cys-OH emerges as a key player in advancing immunotherapeutic approaches, offering new avenues for combating challenging medical conditions.

Toll-like Receptor Studies: Serving as a valuable tool in toll-like receptor investigations, Pam3-Cys-OH provides a well-defined agonist for studying TLR2. Researchers harness its properties to unravel the intricate signaling pathways and physiological responses triggered by TLR activation, deepening our understanding of innate immunity.

Inflammatory Disease Models: In preclinical models, Pam3-Cys-OH is instrumental in studying inflammatory processes and testing anti-inflammatory drugs. By mimicking bacterial components, it allows researchers to simulate infection-induced inflammation and evaluate potential therapeutics. These studies are paramount for shaping treatments against inflammatory diseases like sepsis and rheumatoid arthritis, offering hope for improved patient outcomes and quality of life.

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