Permeability of membranes to amino acids and modified amino acids: Mechanisms involved in translocation

  title={Permeability of membranes to amino acids and modified amino acids: Mechanisms involved in translocation},
  author={Ajoy C. Chakrabarti},
  journal={Amino Acids},
SummaryThe amino acid permeability of membranes is of interest because they are one of the key solutes involved in cell function. Membrane permeability coefficients (P) for amino acid classes, including neutral, polar, hydrophobic, and charged species, have been measured and compared using a variety of techniques. Decreasing lipid chain length increased permeability slightly (5-fold), while variations in pH had only minor effects on the permeability coefficients of the amino acids tested in… 

Different effects of cholesterol on membrane permeation of arginine and tryptophan revealed by bias-exchange metadynamics simulations.

Improved microscopic understanding of amino-acid permeation through cholesterol-containing DPPC membrane systems is provided and strong but different orientation dependence between Arg+ and Trp permeations is observed.

Dynamic covalent transport of amino acids across lipid bilayers.

The results demonstrate the potential of hemiaminal formation for the facilitated transport of substrates containing primary and secondary amino groups for transmembrane transport of amino acids by the formation of a three-component assembly.

Effects of Phospholipid Composition on the Transfer of a Small Cationic Peptide Across a Model Biological Membrane.

The study reveals that protonated lysine residues can be buried further inside an ether lipid membrane than an ester lipid membrane, while branched lipids are found to stabilize less the charged form compared to their unbranched lipid chain counterparts.

A membrane transporter for tryptophan composed of RNA.

A specific passive membrane transporter whose properties overlap those of single-molecule transporter proteins, can be made of RNA alone, suggesting that RNA aggregation is required for both binding and enhanced tryptophan permeability.

Preferential Equilibrium Partitioning of Positively Charged Tryptophan into Phosphatidylcholine Bilayer Membranes

It is demonstrated that Trp+ partitions into the lipid bilayer membrane to a greater degree than Trp– by interacting with the ester linkage of a phosphatidylcholine lipid, where it is stabilized by the electron withdrawing glycerol functional group.

Amino acid capture by aqueous interfaces. Implications for biological uptake.

It is shown that neutral tautomers exhibit a noticeable affinity for the interface that increases with increasing hydrophobicity of the side chain, and a two-step mechanism for the water-to-organic phase transfer that involves neutralization of a partially hydrated zwitterion in the organic layer prior to uptake into the bulk is suggested.

Unassisted transport of N-acetyl-L-tryptophanamide through membrane: experiment and simulation of kinetics.

The permeation of a blocked tryptophan through a 1,2-dioleoyl-sn-glycero-3-phosphocholine membrane is investigated to probe unassisted or physical transport and suggests critical dependence of transport time on permeant size and hydrophilicity.

Kinetics and thermodynamics of chlorpromazine interaction with lipid bilayers: effect of charge and cholesterol.

A detailed study on the kinetics and thermodynamics for the interaction of chlorpromazine (CPZ), an antipsychotic drug used in the treatment of schizophrenia, with neutral and negatively charged lipid bilayers is described.

Chiral selective transmembrane transport of amino acids through artificial channels.

Peptide-appended pillar[n]arene derivatives have been synthesized andKinetic measurements using the fluorescent labeling method with lipid vesicles revealed that these molecules can efficiently mediate the transport of amino acids across lipid membranes at a very low channel-to-lipid ratio.

In vitro intestinal absorption of amino acid mixtures extracted from codfish (Gadus morhua L.) salting wastewater

Values for apparent permeability coefficients suggest that amino acids are very likely to be absorbed in humans, and results show that isotonic mixture of amino acids extracted from codfish salting wastewater could be used in food, feed, cosmetic and pharmaceutical formulations.



Selective diffusion of neutral amino acids across lipid bilayers.

Permeability of lipid bilayers to amino acids and phosphate.

Permeability of amino acids into liposomes.

Influence of charge, charge distribution, and hydrophobicity on the transport of short model peptides into liposomes in response to transmembrane pH gradients.

It is concluded that different charge distributions in short peptides of identical amino acid composition can strongly influence the ability of these groups to associate with and permeate across lipid bilayers.

Effects of surface charges and cholesterol content on amino acid permeabilities of small unilamellar vesicles.

The permeabilities of amino acids through bilayer lipid membranes were determined using small unilamellar vesicles (SUV) and an increase in the amount of negative charges introduced by dicetylphosphate enhanced the permeability of the positively charged amino acid.

Uptake of basic amino acids and peptides into liposomes in response to transmembrane pH gradients.

Permeability of lipid bilayers to water and ionic solutes.

Co- and counter-transport mechanisms in cell membranes.

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    Annual review of physiology
  • 1980
This review concerns only the specific transport mechanisms that permit the coupling of transport between molecules that are cases of facilitated transport.

Permeability of small nonelectrolytes through lipid bilayer membranes

Diffusion of small nonelectrolytes through planar lipid bilayer membranes was examined by correlating the permeability coefficients of 22 solutes with their partition coefficients between water and four organic solvents, and the molecular volume dependence of solute permeability suggests that the membrane barrier behaves more like a polymer than a liquid hydrocarbon.