Tripalmitoyl pentapeptide | CAS#87173-03-3 | Mitogen from E coli lipoprotei

MedKoo Cat#: 596808 | Name: Tripalmitoyl pentapeptide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Tripalmitoyl pentapeptide

CAS#87173-03-3

Theoretical Analysis

MedKoo Cat#: 596808

Name: Tripalmitoyl pentapeptide

CAS#: 87173-03-3

Chemical Formula: C67H124N6O14S

Exact Mass: 1268.8896

Molecular Weight: 1269.81

Elemental Analysis: C, 63.37; H, 9.84; N, 6.62; O, 17.64; S, 2.52

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

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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

Instruction

View handling instruction

Preparing Stock Solutions

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

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. 3: Bessler WG, Heinevetter L, Wiesmüller KH, Jung G, Baier W, Huber M, Lorenz AR, Esche UV, Mittenbühler K, Hoffmann P. Bacterial cell wall components as immunomodulators--I. Lipopeptides as adjuvants for parenteral and oral immunization. Int J Immunopharmacol. 1997 Sep-Oct;19(9-10):547-50. PubMed PMID: 9637352. 4: Dmitriev BA, Ovchinnikov MV, Lapina EB, Pluzhnikova GN, Lopyrev IV, Chernyak AYa. Glycopeptidolipids--a new class of artificial antigens with carbohydrate determinants. Synthesis of artificial antigen with type-specific oligosaccharide hapten from Neisseria meningitidis group B. Glycoconj J. 1992 Aug;9(4):168-73. PubMed PMID: 1422136. 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.