WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H596808
CAS#: 87173-03-3
Description: Tripalmitoyl pentapeptide is a Mitogen from E coli lipoprotein; synthetic lipopeptide; analogue of the N-terminal part of bacterial lipoprotein; constitutes a potent macrophage & B lymphocyte activator.
Hodoodo Cat#: H596808
Name: Tripalmitoyl pentapeptide
CAS#: 87173-03-3
Chemical Formula: C67H124N6O14S
Exact Mass: 1,268.89
Molecular Weight: 1,269.810
Elemental Analysis: C, 63.37; H, 9.84; N, 6.62; O, 17.64; S, 2.52
This product is not in stock, which may be available by custom synthesis.
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Synonym: Tripalmitoyl pentapeptide; P3C-Ssna; P3C Ssna P3CSsna; Bppp-cssaa; Bppp cssaa; Bpppcssaa
IUPAC/Chemical Name: S-(2,3-bis(palmitoyloxy)propyl)-N-palmitoyl-L-cysteinyl-L-seryl-L-seryl-L-asparaginyl-L-alanine
InChi Key: LXPAYSRLFXJBQQ-NXCWWGNDSA-N
InChi Code: InChI=1S/C67H124N6O14S/c1-5-8-11-14-17-20-23-26-29-32-35-38-41-44-60(77)70-58(66(83)73-57(49-75)65(82)72-56(48-74)64(81)71-55(47-59(68)76)63(80)69-53(4)67(84)85)52-88-51-54(87-62(79)46-43-40-37-34-31-28-25-22-19-16-13-10-7-3)50-86-61(78)45-42-39-36-33-30-27-24-21-18-15-12-9-6-2/h53-58,74-75H,5-52H2,1-4H3,(H2,68,76)(H,69,80)(H,70,77)(H,71,81)(H,72,82)(H,73,83)(H,84,85)/t53-,54?,55-,56-,57-,58-/m0/s1
SMILES Code: C[C@@H](C(O)=O)NC([C@H](CC(N)=O)NC([C@H](CO)NC([C@H](CO)NC([C@H](CSCC(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O)NC(CCCCCCCCCCCCCCC)=O)=O)=O)=O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 1,269.81 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Levy O, Coughlin M, Cronstein BN, Roy RM, Desai A, Wessels MR. The adenosine system selectively inhibits TLR-mediated TNF-alpha production in the human newborn. J Immunol. 2006 Aug 1;177(3):1956-66. PubMed PMID: 16849509; PubMed Central PMCID: PMC2881468.
2: Nakata T, Yasuda M, Fujita M, Kataoka H, Kiura K, Sano H, Shibata K. CD14 directly binds to triacylated lipopeptides and facilitates recognition of the lipopeptides by the receptor complex of Toll-like receptors 2 and 1 without binding to the complex. Cell Microbiol. 2006 Dec;8(12):1899-909. Epub 2006 Jul 11. PubMed PMID: 16848791.
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5: Kellner J, Erhard M, Schranner I, Lösch U. The influence of various adjuvants on antibody synthesis following immunization with an hapten. Biol Chem Hoppe Seyler. 1992 Jan;373(1):51-5. PubMed PMID: 1536694.
6: Bessler WG. Synthetic lipopeptide immunomodulators derived from bacterial lipoprotein: tools for the standardization of in vitro assays. Dev Biol Stand. 1992;77:49-56. PubMed PMID: 1426672.
7: Kleine B, Biesert L, Bessler WG. The membrane protein compositions of lipopolysaccharide- or lipoprotein-activated B lymphoblasts from C57BL LPS-responder and non-responder mice are qualitatively indistinguishable. Res Immunol. 1989 Sep;140(7):685-95. PubMed PMID: 2595080.
8: Lovett DH, Bursten SL, Gemsa D, Bessler W, Resch K, Ryan JL. Activation of glomerular mesangial cells by gram-negative bacterial cell wall components. Am J Pathol. 1988 Dec;133(3):472-84. PubMed PMID: 3059803; PubMed Central PMCID: PMC1880810.
9: Hauschildt S, Wagner-Roos LM, Wiesmüller KH, Jung G, Bessler WG. Phosphatidylinositol metabolism and protein kinase C activation in leukocytes by lipopeptides. Immunobiology. 1988 Jul;177(3):267-77. PubMed PMID: 3169841.
10: Brade L, Bessler WG, Brade H. Mitogenic activities of synthetic Escherichia coli lipid A and a synthetic partial structure (tripalmitoyl pentapeptide) of E. coli lipoprotein. Infect Immun. 1988 May;56(5):1382-4. PubMed PMID: 3281910; PubMed Central PMCID: PMC259838.
11: Kleine B, Sprenger R, Martinez-Alonso C, Bessler WG. Polyclonal B-cell activation by a synthetic analogue of bacterial lipoprotein is functionally different from activation by bacterial lipopolysaccharide. Immunology. 1987 May;61(1):29-34. PubMed PMID: 3495485; PubMed Central PMCID: PMC1453309.
12: Biesert L, Scheuer W, Bessler WG. Interaction of mitogenic bacterial lipoprotein and a synthetic analogue with mouse lymphocytes. Isolation and characterization of binding proteins. Eur J Biochem. 1987 Feb 2;162(3):651-7. PubMed PMID: 3549292.
13: Lex A, Wiesmüller KH, Jung G, Bessler WG. A synthetic analogue of Escherichia coli lipoprotein, tripalmitoyl pentapeptide, constitutes a potent immune adjuvant. J Immunol. 1986 Oct 15;137(8):2676-81. PubMed PMID: 3531339.
14: Scheuer WV, Biesert L, Bessler WG. Binding of a synthetic analogue of mitogenic bacterial lipoprotein to murine major histocompatibility complex (MHC) gene products. Biol Chem Hoppe Seyler. 1986 Oct;367(10):1085-94. PubMed PMID: 3491614.
15: Bessler WG, Bessler U, Eck G, Scheuer WV, Suhr B. [In vitro methods for testing of plant derived, bacterial and synthetic agents and toxins with the use of leukocyte primary cell cultures and cell lines]. Arzneimittelforschung. 1985;35(8):1209-15. German. PubMed PMID: 2416324.
16: Johnson RB, Köhl S, Wiesmüller K, Jung G, Bessler WG. Synthetic analogues of the N-terminal lipid part of bacterial lipoprotein are B-lymphocyte mitogens in vitro and in vivo. Immunobiology. 1983 Jul;165(1):27-35. PubMed PMID: 6350164.
17: Wiesmüller KH, Bessler W, Jung G. Synthesis of the mitogenic S-[2,3-bis(palmitoyloxy)propyl]-N-palmitoylpentapeptide from Escherichia coli lipoprotein. Hoppe Seylers Z Physiol Chem. 1983 May;364(5):593-606. PubMed PMID: 6347861.
