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670820

Sigma-Aldrich

Pam3-Cys-OH

≥98.0% (TLC), for peptide synthesis

Synonym(s):

N-α-Palmitoyl-S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-L-cysteine, Palmitoyl-Cys((RS)-2,3-di(palmitoyloxy)-propyl)-OH

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About This Item

Empirical Formula (Hill Notation):
C54H103NO7S
CAS Number:
Molecular Weight:
910.46
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22

product name

Pam3-Cys-OH, ≥98.0% (TLC)

Quality Level

Assay

≥98.0% (TLC)

reaction suitability

reaction type: solution phase peptide synthesis

application(s)

peptide synthesis

SMILES string

CCCCCCCCCCCCCCCC(=O)N[C@@H](CSCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(O)=O

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

General description

Pam3-Cys-OH is a lipopeptide containing a cysteine residue at the C-terminus, often used in solid phase peptide synthesis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Nishi Shakya et al.
Peptides, 32(10), 2131-2133 (2011-10-01)
Prophylactic potential of synthetic bacterial lipopeptide and a TLR2 agonist, Pam3Cys was first evaluated against experimental visceral leishmaniasis in rodent model. After establishing the potential its effect on therapeutic efficacy of miltefosine was also studied. Pam3Cys showed 74.64% inhibition in
Lipoconjugates for the noncovalent generation of microarrays in biochemical and cellular assays
A Hoff, et al.
Chembiochem, 3, 1183-1191 (2002)
Pitchaimani Kandasamy et al.
The Journal of biological chemistry, 286(10), 7841-7853 (2011-01-06)
Mycoplasma pneumoniae is a human pathogen causing respiratory infections that are also associated with serious exacerbations of chronic lung diseases. Membranes and lipoproteins from M. pneumoniae induced a 4-fold increase in arachidonic acid (AA) release from RAW264.7 and a 2-fold
Amrita D Joshi et al.
Journal of leukocyte biology, 83(2), 314-324 (2007-11-22)
Macrophages play a pivotal role in innate and acquired immune responses to Schistosoma mansoni. Classical (M1) or alternative (M2) activation states of these cells further delineate their roles in tissue damage through innate immunity or fibrotic remodeling, respectively. In the
Peter M Moyle et al.
Current medicinal chemistry, 15(5), 506-516 (2008-02-22)
Despite the important role of adjuvants for vaccine development, relatively few adjuvants have been successfully incorporated into vaccines intended for human administration. This is in part due to the high toxicity associated with many experimental adjuvants. This lack of choice

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