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Lipidated Custom Peptides

Lipidation is a peptide modification that involves the addition of lipid molecule to a peptide sequence. Lipopeptides are of particular interest for vaccine development because it avoids the use of the sometimes toxic adjuvants while still generating a comprehensive immune response. Synthetic peptides alone are not enough to generate an immune response and therefore an immunoadjuvant is typically employed to enhance the response. Alternatives to the classical Freund's adjuvants have had some success in peptide vaccine work that include conjugations to bacterial and viral carrier proteins, immunostimulating complexes, and branched multiple antigenic peptides (MAPS).

peptide lipid conjugates

Lipopeptides first entered into vaccine development after the observation in the early 1980's by Hopp and co-workers that found improved anti-hepatitis surface antigen response in a peptide conjugated to a dipalmityl-lysine moiety. The reason for this finding is that while short peptides may contain cytotoxic T lymphocytes (CTL) that bind to MHC class I molecules, they fail to prime CD8+ T-cell responses in vivo. This was further confirmed in the early 1990's by Rammensee and co-workers who showed that an influenza lipopeptide (without the need for an adjuvant) elicited CTL responses whereas the corresponding peptide without lipid conjugation did not.

CPC Scientific has extensive experience and knowledge in synthesizing peptides containing lipid moieties and can link virtually any peptide sequence to lipids that include, palmitoyl, dipalmitoyl, myristic acid, geranyl, farnesyl, geranylgeranyl, and more.

Custom Peptide Synthesis NOTA chelate

Noland, Cameron L., et al. "Structural insights into lipoprotein N-acylation by Escherichia coli apolipoprotein N-acyltransferase." Proceedings of the National Academy of Sciences 114.30 (2017): E6044-E6053.

Custom Lipopeptide Citations

"The peptide library in Table S1 (Supporting Information) was synthesized for initial screening with FAM-conjugated lysine at the C-terminal end of the membrane-interactive peptide and with or without D[KLAKLAK]2 on the C-terminus using standard Fmoc chemistry by the Koch Institute Swanston Biotechnology Center. All peptides were synthesized with N-terminal myristic acid and C-terminal amine. They were resynthesized to 80% purity in small lots for follow-up in vitro studies. For the animal studies, larger quantities of the peptides were synthesized by CPC Scientific to 90% purity"

1. Kwon, Ester J., et al. "Porous Silicon Nanoparticle Delivery of Tandem Peptide Anti-Infectives for the Treatment of Pseudomonas aeruginosa Lung Infections." Advanced Materials 29.35 (2017).Learn More »

"Myristoyl-transportan−LyP-1 tandem peptide was synthesized by CPC Scientific (sequence: myr-GGWTLNSAGYLLGKINLKALAALAKKIL-GGGG-CGNKRTRGC, Cys−Cys bridge). Fluorescently labeled peptide was synthesized bySelleckchem, with a tetramethylrhodamine (TAMRA)-tagged lysine inserted into the glycine spacer. FAM-labeled LyP-1 bearing an azide (azidoacetyl-GGG-cyclo-(EGNKRTRGK)), FAM-labeled LyP-1 bearing a cysteine (C-K(5FAM)-C6-cyclo-(CGNKRTRGC)) and transportan bearing a C-terminal cysteine (myristic acid-GGWTLNSAGYLLGKINLKALAALAKKILC) were synthesized by CPC Scientific, Inc."

2. Lo, Justin H., et al. "A comparison of modular PEG incorporation strategies for stabilization of peptide-siRNA nanocomplexes." Bioconjugate Chemistry (2016): 27 (10), pp 2323–2331Learn More »

"[palmitoylated peptides] were synthesized by CPC Scientific Inc. (Sunnyvale, CA, USA), each obtained as a white lyophilised powder and stored at 4 °C protected from light. All peptides were synthesized by peptide solid phase synthesis."

3. Longo, Edoardo, et al. "The effect of palmitoylation on the conformation and physical stability of a model peptide hormone." International Journal of Pharmaceutics 472.1 (2014): 156-164.Learn More »

"[The peptides] were synthesized by CPC Scientific with N-terminal myristic acid."

4. Kwon, Ester J., et al. "Neuron-targeted nanoparticle for siRNA delivery to traumatic brain injuries." ACS Nano 10.8 (2016): 7926-7933.Learn More »

"pTP-TAMRA-iRGD (CH3(CH)15-GWTLNSAGYLLGKINLKALAALAKKILGGK(TAMRA)GGCRGDKGPDC, Cys-Cys bridge) was synthesized by CPC Scientific. Myristoyl-transportan-LyP-1 tandem peptide was synthesized by CPC Scientific (sequence: myr-GGWTLNSAGYLLGKINLKALAALAKKIL-GGGG-CGNKRTRGC, Cys-Cys bridge). Fluorescently-labeled peptide was synthesized by Selleckchem, with a tetramethylrhodamine (TAMRA) tagged lysine inserted into the glycine spacer. FAM-labeled LyP-1 bearing an azide (Azidoacetyl-GGG-cyclo-(EGNKRTRGK)), FAM-labeled LyP-1 bearing a 62 cysteine (C-K(5FAM)-C6-cyclo(CGNKRTRGC)) and transportan bearing a C-terminal cysteine (myristic acid-GGWTLNSAGYLLGKINLKALAALAKKILC) were synthesized by CPC Scientific, Inc...pTP-SWCEPGWCR (“pTP-PANC”) peptide (full sequence: palmitoylGWTLNSAGYLLGKINLKALAALAKKILGGKKKKGGSWCEPGWCR) was synthesized by CPC Scientific."

5. Lo, Justin Han Je. Targeting nucleic acids for pancreatic cancer: disease modeling and therapy. Diss. Massachusetts Institute of Technology, 2015.Learn More »

"Pal peptideshort (Pam2Cys-SSNKNGGK-Biotin; CPC Scientific, Inc.)"

6. Noland, Cameron L., et al. "Structural insights into lipoprotein N-acylation by Escherichia coli apolipoprotein N-acyltransferase." Proceedings of the National Academy of Sciences 114.30 (2017): E6044-E6053.Learn More »

ABBREV. FULL NAME IUPAC NAME
PAL Palmitic acid Hexadecanoic acid
MYR Myristic acid Tetradecanoic acid
GER Geranyl group (2E)-3,7-dimethylocta-2,6-dien-1-yl
FAR Farnesyl group (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl
GGER Geranylgeranyl group (2E,4E,6E)-3,5,7,11-Tetramethyldodeca-2,4,6,10-tetraene-1-yl