Lipid Membranes

Permeability depends on chirality

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Science  16 Jul 2021:
Vol. 373, Issue 6552, pp. 292-293
DOI: 10.1126/science.373.6552.292-b

In biological systems, nucleic acids, proteins, and lipids, which are the building blocks of cells, have set chirality, whereas natural secondary metabolites and synthetic drugs can have more varied stereochemistry, even when using familiar elements such as amino acids or sugars. Hu et al. investigated how varying the chirality of alkyne-labeled amino acids changed their permeability through a phospholipid bilayer in a specially designed microfluidics setup. There were considerable differences for some amino acids and dipeptides, which could be eliminated by using achiral lipids or reversed by using abiological lipids of opposite chirality.

Nat. Chem. 10.1038/s41557-021-00708-z (2021).

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