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Published on 27/04/2020
Lipidated “fatty” amino acids have a number of intriguing applications, the most well-known being the prolongation of circulation half-life of peptide therapeutics by binding to serum albumin. This ubiquitous serum protein is able to prolong the plasma half-life of otherwise rapidly cleared drugs. Well-known examples of this application are the blockbuster drugs Liraglutide and Semaglutide.
Fatty acid linkers of Semaglutide (FAA7640) and Liraglutide (FAA3790)
Besides the above-mentioned applications, fatty amino acids have various other interesting properties. They may increase cell permeability of compounds and even allow substances to cross the blood-brain barrier (Blanchfield et al. 2003; Bulaj et al. 2008). Lipidation can be a means to make use of albumin as a carrier for cancer therapeutics (Hoogenboezem et al. 2018). Moreover, lipopeptides are able to trigger a T-cell dependent immune response and are thus of great interest for vaccine development (Zhu et al. 2004; Zhang et al. 2005). Finally, lipidated peptides are increasingly found in cosmetics as anti-ageing agents (Robinson et al. 2005).
We have recently added a large variety of lipidated amino acids to our portfolio. Among those are:
✓ Derivatives of Lys, Ser and Asp that give easy access to isostructural analogues
✓ Derivatives with a variety of terminal functional groups
✓ Production routes are scalable
✓ Longer homologues of norleucine & longer fatty amino acid homologues with different terminal functional groups are in development and can be supplied on custom synthesis basis.
✓ Derivatives of Arg, Asn, Cys, Gln, His, Hyp, Gly, Pro, Trp, Tyr that give easy access to new analogues.
✓ Two fatty acid residues can be attached on the same amino acid in some cases.
✓ Published applications: antimicrobial peptides, adjuvants, cancer vaccines, novel receptor agonist, cancer imaging, and peptide amphiphiles (PAs) with unusual thermal stability.
✓ Production routes are scalable.