Aminooxyacetic acid

Tiburzy (22,31) obtained similar results by application of the PAL inhibitor aminooxyacetic acid (AOA). However, AOA does not specifically inhibit PAL (99), and PAL is not only involved in lignin biosynthesis (100). Thus, AOA and the related inhibitor aminooxyphenyl propionic acid (AOPP) (101,102) inhibit the biosynthesis of lignin (103,104), anthocyanins (105), other flavonoids (106), and conjugates of cinnamic acids (107) via PAL, as well as ethylene (108-110) via a pyridoxal phosphate dependent enzyme (110,111). In view of the possible function of phenolic compounds as phytoalexins (21,112,113) and the well documented role of ethylene in some resistance reactions (114-116), the above cited experiments with AOA (22,... 

A solution of the step 1 product (0.023 mol) dissolved in 100 ml of chloroform was treated with Boc-aminooxyacetic acid (1.5 eq) and l-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide (1.5 eq) and then stirred overnight under nitrogen. The mixture was concentrated, the residue was chromatographed as described in step 1, and 4.6 g of product isolated. 

Osterloh, J. Xiwen, H. (1990) Effects of 1,3-dichloropropene on the kidney of Fisher 344 rats after pretreatment with diethyl maleate, buthionine sulfoximine, and aminooxyacetic acid. J. Toxicol, environ. Health, 28, 247-255... 

Similar trends were noted in fasted male Sprague-Dawley rats following a 4-h inhalation exposure to 180-200 ppm [720-800 mg/m ] vinylidene chloride (Cavelier et al., 1996). Analysis of urine and serum for biochemical markers of toxicity 24 h after exposure revealed increased toxicity following vinylidene chloride exposure. Levels of marker enzymes were similar to control values following pretreatment with aminooxyacetic acid. No effect was noted on vinylidene chloride toxicity following acivicin treatment and only slight increases in vinylidene chloride toxicity were obsen ed following methimazole pretreatment. 

Displacement of the methylthio group from (679) with aminooxyacetic acid gave (680), which cyclized to (681) upon attempted esterification (70TL1879). 

Aminooxyacetic acid Significantiy reduces toxicity of DCVC in vivo and in vitro Inhibits (S-lyase activity... 

Figure 9 Handling of 6-PG in renal proximal tubular cells. Abbreviations BBM, brush border plasma membrane BLM, basolateral plasma membrane 6-MP, 6-mercaptopurine 6-PG, S-(6-purinyl) glutathione 6-PC, S-(6-purinyl)-L-cysteine NAcPC, w-acetyl-S-(6-purinyl)-L-cysteine GGT, y-glutamyltransferase DP, dipeptidase P-lyase, cysteine conjugate P-lyase PLP, pyridoxal phosphate XO, xanthine oxidase 6-ThXan, 6-thioxanthine 6-ThUrate, 6-thiourate AOAA, aminooxyacetic acid and Av /, membrane potential. (Adapted from Ref. 30.)...

There exists a large body of literature on the turnover of GABA in brain In this review I have recommended the use of specific GABA-T inhibitors, such as 7-vinyl-GABA, gabaculine, and aminooxyacetic acid, that can be administered either systemically or intracerebrally... 

Pericic D, Eng N, and Walters J R (1978) Postmortem and aminooxyacetic acid-induced accumulation of GABA- Effect of 7-butyrolactone and picrotoxin. /. Neurochem 30, 767-774,... 

Walaas I. and Fonnum F (1980) Biochemical evidence for glutamate as a transmitter in hippocampal efferents to the basal forebrain and hypothalamus in rat brain Neuroscience 5, 1691-1698 Wallach D P. (1961) Studies on the GABA pathway. I. The inhibition of 7-aminobutyric acid-a-ketoglutanc acid transaminase in vitro and in vivo by U-7524 (aminooxyacetic acid) Biochem Pharmacol. 5, 323-331. 

Walters J R., Eng N, Pericic D, and Miller L. P (1978) Effects of aminooxyacetic acid and L-glutamic acid-7-hydrazide on GABA metabolism in specific brain regions. / Neurochem 30, 759-766... 

D-phenylalanine, the sterioisomer of the naturally occurring L-phenylalanine, inhibits the PAL activity. Szkutnicka and Lewak (18) found that the application of this compound to germinating seeds caused an increase in the PAL level. They attributed this to the decrease in the production of cinnamic acid and compounds derived therefrom. Similar results have been obtained by Amrhein and Gerhardt (19) with the PAL-inhibitors, L-a-aminooxy-8-phenylpropionic acid and a-aminooxyacetic acid on gherkin seedlings. They found that the synthesis of hydroxycinnamic acids was inhibited and that the PAL level increased. This increase was suppressed when tr<2 s-cinnamic acid was applied. 

Keywords Phenylpropanoids - phenylalanine ammonia-lyase phenylalanine transamination - aminooxyacetic acid - aminooxyphenyIpropionic acid... 

This indicates that repression by accumulating products may play a regulatory role in the cinnamic acid metabolism of Cucumis, In other organisms, however, e.g., in Fagopyrum esculen-turn, this regulatory principle could not be substantiated. Here PAL activity after illumination showed a similar time course with and without a-aminooxyacetic acid. 

Fisher MA, Hagen DQ, Colvin RB. Aminooxyacetic acid Interactions with gamma-aminobutyric acid and the blood—brain barrier. Science. 1966 153 1668-1670. 

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