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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:
87420-41-5
Molecular Weight:
910.46
MDL number:
MFCD00153468
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24885087
NACRES:
NA.22

product name

Pam3-Cys-OH, ≥98.0% (TLC)

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

Related Categories

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ7225
BCCD0173
BCCC0039
BCBV8395
BCBQ5485V

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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
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
Lipoconjugates for the noncovalent generation of microarrays in biochemical and cellular assays
A Hoff, et al.
Chembiochem, 3, 1183-1191 (2002)
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
Gerben Ferwerda et al.
Cellular microbiology, 10(10), 2058-2066 (2008-06-14)
The beta-glucan receptor dectin-1 and Toll-like receptors TLR2 and TLR4 are the main receptors for recognition of Candida albicans by the innate immune system. It has been reported that dectin-1 amplifies TLR2-dependent induction of cytokines in mouse models. In the
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