Peptide lipidation in lysophospholipid micelles and lysophospholipid-enriched membranes

Ismail, Vian S.; Britt, Hannah M.; Mosely, Jackie A.; Sanderson, John M.

doi:10.1039/d1fd00030f

Cited by 1 publication

(2 citation statements)

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“…It has also been demonstrated that peptides are able to undergo similar processes with lysolipids. 280 A consequence of peptide lipidation in this manner is expected to be an increase in the membrane affinity of the lipidated peptide. This will be reflected by irreversible membrane binding.…”

Section: Intrinsic Lipidationmentioning

confidence: 99%

“…Generally, both higher temperatures and increased salt concentrations favored the reaction, but the effects of other parameters were found to be small. It has also been demonstrated that peptides are able to undergo similar processes with lysolipids . A consequence of peptide lipidation in this manner is expected to be an increase in the membrane affinity of the lipidated peptide.…”

Section: Aminolysis and Transesterificationmentioning

confidence: 99%

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The Chemical Reactivity of Membrane Lipids

Duché,

Sanderson

2024

Chem. Rev.

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It is well-known that aqueous dispersions of phospholipids spontaneously assemble into bilayer structures. These structures have numerous applications across chemistry and materials science and form the fundamental structural unit of the biological membrane. The particular environment of the lipid bilayer, with a water-poor low dielectric core surrounded by a more polar and better hydrated interfacial region, gives the membrane particular biophysical and physicochemical properties and presents a unique environment for chemical reactions to occur. Many different types of molecule spanning a range of sizes, from dissolved gases through small organics to proteins, are able to interact with membranes and promote chemical changes to lipids that subsequently affect the physicochemical properties of the bilayer. This Review describes the chemical reactivity exhibited by lipids in their membrane form, with an emphasis on conditions where the lipids are well hydrated in the form of bilayers. Key topics include the following: lytic reactions of glyceryl esters, including hydrolysis, aminolysis, and transesterification; oxidation reactions of alkenes in unsaturated fatty acids and sterols, including autoxidation and oxidation by singlet oxygen; reactivity of headgroups, particularly with reactive carbonyl species; and E/Z isomerization of alkenes. The consequences of reactivity for biological activity and biophysical properties are also discussed. CONTENTS

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Section: Intrinsic Lipidationmentioning

confidence: 99%

Section: Aminolysis and Transesterificationmentioning

confidence: 99%