Synthesis and transport applications of 3-aminobicyclo[3,2,1]octane-3-carboxylic acids
- 1 October 1983
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 26 (10), 1374-1378
- https://doi.org/10.1021/jm00364a008
Abstract
The isomeric 3-aminobicyclo[3.2.1]octane-3-carboxylic acids were synthesized and compared with the widely used (1R,2S,4S)-2-aminobicyclo[2.2.1]heptane-2carboxylic acid as to specificity to the Na+-independent membrane transport system L of the Ehrlich ascites tumor cell [mouse] and of the rat hepatoma cell line HTC. The presence of an additional methylene group in the ring system leads to an optically symmetrical amino acid, with the advantages that the product is devoid of isomeric contamination. Hence optical resolution is not necessary to secure a homogeneous test substrate for discrimination of amino acid transport systems. Through its inhibitory action on the cellular uptake of known system-specific amino acids, the bicyclo[3.2.1]octane amino acid proved more reactive than the bicycloheptane analog with the Na+-independent amino acid transport system of the test cells and not perceptibly reactive with the accompanying Na+-dependent systems. Recent evidence of the presence of a 2nd component of Na+-independent amino acid transport, beyond system L, increases the importance of securing a variety of possibly discriminatory model substrates.This publication has 11 references indexed in Scilit:
- The cluster-tray method for rapid measurement of solute fluxes in adherent cultured cellsAnalytical Biochemistry, 1981
- Characteristics of system ASC for transport of neutral amino acids in the isolated rat hepatocyte.Journal of Biological Chemistry, 1981
- l-Tryptophan transport in human red blood cellsBiochimica et Biophysica Acta (BBA) - Biomembranes, 1980
- The structure of cis-bicyclo[3.3.O]octane-3-spiro-5'-hydantoinActa crystallographica Section B, Structural science, crystal engineering and materials, 1979
- SYNTHETIC AMINO ACIDS AND THE NATURE OF l‐DOPA TRANSPORT AT THE BLOOD‐BRAIN BARRIERJournal of Neurochemistry, 1975
- A Distinct Na+-requiring Transport System for Alanine, Serine, Cysteine, and Similar Amino AcidsJournal of Biological Chemistry, 1967
- Discrimination of Single Transport SystemsThe Journal of general physiology, 1966
- Induction of tyrosine alpha-ketoglutarate transaminase by steroid hormones in a newly established tissue culture cell line.Proceedings of the National Academy of Sciences, 1966
- Distinct Mediating Systems for the Transport of Neutral Amino Acids by the Ehrlich CellJournal of Biological Chemistry, 1963
- Uptake of Pyridoxal and Pyridoxal Phosphate by Ehrlich Ascites Tumor CellsJournal of Biological Chemistry, 1961