PMID: 6413692Oct 1, 1983Paper

Synthesis and transport applications of 3-aminobicyclo[3.2.1] octane-3-carboxylic acids

Journal of Medicinal Chemistry
H N ChristensenC Avendaño

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-2-carboxylic acid as to specificity to the Na+-independent membrane transport system L of the Ehrlich ascites tumor cell 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 analogue 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 second component of Na+-independent amino acid transport, beyond system L, increases the importance of securing a variety of possibly discriminatory model substrates.

Citations

Nov 1, 1990·Developmental Biology·L J Van WinkleR L Garton
Sep 9, 1985·Biochimica Et Biophysica Acta·D L Yudilevich, J H Sweiry
Aug 13, 1987·Biochimica Et Biophysica Acta·L J Van Winkle, A L Campione
Dec 1, 1990·Bioscience Reports·A FelipeX Remesar
Jun 19, 2002·CNS Drug Reviews·Konstanty Wiśniewski, Halina Car
Sep 3, 1984·Biochimica Et Biophysica Acta·H N Christensen
Jun 22, 1988·Biochimica Et Biophysica Acta·L J Van WinkleJ M Gorman

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