N-Oleoyl-L-phenylalanine

N-Oleoylphenylalanine (136560-78-6) is an endogenous lipoamino acid produced via the action of a secreted enzyme PM20D1 produced by adipocytes. N-Oleoylphenylalanine binds directly to mitochondria and functions as an endogenous uncoupler of UCP1-independent respiration and is the most potent in the group of structurally different lipoamino acids evaluated. Mice treated with an analog, C18-1-Leu, were found to have improved glucose homeostasis and increased energy expenditure.1

N-Oleoyl-L-phenylalanine is an N-acyl amide[1].

ChEBI: N-oleoyl-L-phenylalanine is an N-acyl-L-phenylalanine resulting from the formal condensation of the carboxy group of oleic acid with the amino group of L-phenylalanine. It is a N-acyl-L-phenylalanine and a fatty amide. It is functionally related to an oleic acid. It is a conjugate acid of a N-oleoyl-L-phenylalaninate.

[1] JONATHAN Z LONG. The Secreted Enzyme PM20D1 Regulates Lipidated Amino Acid Uncouplers of Mitochondria.[J]. Journal of Chemical Theory and Computation, 2016: 424-435. DOI:10.1016/j.cell.2016.05.071