1656-83-3Relevant academic research and scientific papers
Is the Mirror Image a True Reflection? Intrinsic Membrane Chirality Modulates Peptide Binding
Henriques, Sónia Troeira,Peacock, Hayden,Benfield, Aurélie H.,Wang, Conan K.,Craik, David J.
, p. 20460 - 20469 (2019)
Peptides with pharmaceutical activities are attractive drug leads, and knowledge of their mode-of-action is essential for translation into the clinic. Comparison of native and enantiomeric peptides has long been used as a powerful approach to discriminate membrane-or receptor-mediated modes-of-action on the basis of the assumption that interactions with cell membranes are independent of peptide chirality. Here, we revisit this paradigm with the cyclotide kalata B1, a drug scaffold with intrinsic membrane-binding activity whose enantiomer is less potent than native peptide. To investigate this chirality dependence, we compared peptide-lipid binding using mirror image model membranes. We synthesized phospholipids with non-natural chirality and demonstrate that native kalata B1 binds with higher affinity to phospholipids with chirality found in eukaryotic membranes. This study shows for the first time that the chiral environment of lipid bilayers can modulate the function of membrane-active peptides and challenges the view that peptide-lipid interactions are achiral.
Synthetic phospholipids as specific substrates for plasma endothelial lipase
Papillon, Julien P.N.,Pan, Meihui,Brousseau, Margaret E.,Gilchrist, Mark A.,Lou, Changgang,Singh, Alok K.,Stawicki, Todd,Thompson, James E.
, p. 3514 - 3517 (2016/07/21)
We designed and prepared synthetic phospholipids that generate lyso-phosphatidylcholine products with a unique mass for convenient detection by LC–MS in complex biological matrices. We demonstrated that compound 4, formulated either as a Triton X-100 emulsion or incorporated in synthetic HDL particles can serve as a substrate for plasma EL with useful specificity.
Differential interaction of an AmB Analogue and ergosterol in enantiomeric membranes
Jeon, Ock-Youm,Carreira, Erick M.
supporting information; experimental part, p. 1772 - 1775 (2010/09/07)
An amphotericin B derivative exhibits differential interaction with vesicles formed from either natural (R)-or unnatural (S)-POPC and ergosterol. This implicates a close association between the polyene macrolide and the phospholipid bilayer and may account for its increased antifungal activity.
The efficient synthesis of mixed diacyl phospholipids with polyunsaturated fatty acid in sn-2 position of glycerol
Xia, Jie,Hui, Yong-Zheng
, p. 3019 - 3021 (2007/10/03)
A convenient method for synthesis of the mixed-diacyl phospholipid using boron trichloride as an efficient reagent for the removal of benzyl protecting group from polyunsaturated diacylglycerols without affecting the double bond and acyl migration is desc
