Lipopeptides

A lipid molecule is added to a peptide sequence during lipidation, a peptide modification process. Since lipopeptide in skin carecan be used instead of potentially harmful adjuvants while still eliciting a thorough immune response, they are particularly interesting for vaccine development. Because synthetic peptides by themselves are insufficient to elicit an immune response, immunoadjuvants are frequently used to strengthen the reaction. In the development of peptide vaccines, alternatives to the traditional Freund's adjuvants have met with some success. These include conjugations to viral and bacterial carrier proteins, immunostimulating complexes, and branching multiple antigenic peptides (MAPS).

After Hopp and colleagues discovered in the early 1980s that a peptide conjugated to a dipalmityl-lysine moiety increased anti-hepatitis surface antigen response, lipopeptideswere initially used in vaccine development.[1] This result is explained by the fact that, despite the possibility of short peptides containing cytotoxic T cells (CTL) that bind to MHC class I molecules, they are unable to prime CD8+ T-cell responses in vivo. This was further supported by Rammensee and colleagues, who demonstrated in the early 1990s that an influenza lipopeptide (without the need for an adjuvant) evoked CTL responses but the comparable peptide without lipid conjugation did not.

Myristic acid, palmitoyl, dipalmitoyl, geranyl, farnesyl, geranylgeranyl, and other lipids are only a few of the lipids that may be linked to nearly any peptide sequence by CPC due to its significant experience and knowledge in the synthesis of peptides containing lipid moieties.

Common Lipid Abbreviations

	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

References

Hopp, Thomas P. “Immunogenicity of a synthetic HBsAg peptide: enhancement by conjugation to a fatty acid carrier.” Molecular Immunology 21, no. 1 (1984): 13-16.

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