Lipopeptides

A lipid molecule is added to a peptide sequence during lipidation, a peptide
modification process. Since lipopeptide in skin care can 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, lipopeptides were 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
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

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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