Abstract
Acyl transfer from lipids to peptides is able to occur in the absence of enzyme catalysis. This innate reactivity is of fundamental interest, with the potential to influence a number of membrane processes. The kinetics and selectivity of the acylation reaction between melittin (H-GIGAVLKVLTTGLPALISWIKRKRQQ-NH2) and lipids have been revealed by LC-MS and LC-MS/MS approaches. The major sites of acylation on melittin are at the N-terminus and the side chain of Lys-23. With phosphocholines, acylated melittin products are detectable by LC-MS within 4 hours, with little selectivity for transfer from the sn-1 vs the sn-2 position. In PS/PC mixtures, acyl transfer is only observed from the PC component. In PG/PC mixtures, transfer is observed from both the PG and PC components, albeit at a reduced rate when compared to PC-only membranes. Small amounts of double-acylated melittin products are also formed.
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