Reactions of the melatonin metabolite N(1)-acetyl-5-methoxykynuramine with carbamoyl phosphate and related compounds

Journal of Pineal Research
Jana T KueselNelia Aeckerle

Abstract

N-[2-(6-methoxyquinazolin-4-yl)-ethyl] acetamide (MQA) is a compound formed from the melatonin metabolite N(1)-acetyl-5-methoxykynuramine (AMK). We followed MQA production in reaction systems containing various putative reaction partners, in the absence and presence of hydrogen peroxide and/or copper(II). Although MQA may be formally described as a condensation product of either N(1)-acetyl-N(2)-formyl-5-methoxykynuramine (AFMK) with ammonia, or AMK with formamide, none of these combinations led to substantial quantities of MQA. However, MQA formation was observed in mixtures containing AMK, hydrogen peroxide, hydrogen carbonate and ammonia, or AMK, hydrogen peroxide, copper(II) and potentially carbamoylating agents, such as potassium cyanate or, more efficiently, carbamoyl phosphate. In the presence of hydrogen peroxide, copper(II) and carbamoyl phosphate, MQA was the major product obtained from AMK, but the omission of copper(II) mainly led to another metabolite, 3-acetamidomethyl-6-methoxycinnolinone (AMMC). This was caused by nitric oxide (NO) generated under oxidative conditions from carbamoyl phosphate, as shown by an NO spin trap. MQA formation with carbamoyl phosphate was not due to the possible decomposition product, f...Continue Reading

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Citations

Oct 22, 2011·Journal of Experimental Botany·Dun-Xian TanRussel J Reiter
Oct 2, 2014·International Journal of Molecular Sciences·Andrzej T SlominskiTobias W Fischer
Jul 28, 2011·Journal of Pineal Research·Ioannis StratosBrigitte Vollmar
Sep 25, 2012·Journal of Pineal Research·Annia GalanoRussel J Reiter
Nov 24, 2011·Journal of Pineal Research·Sergio A Rosales-CorralRussel J Reiter
Nov 22, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rüdiger Hardeland
Mar 3, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Annia GalanoRussel J Reiter
Jun 12, 2018·Journal of Pineal Research·Annia Galano, Russel J Reiter
Jul 20, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rüdiger Hardeland

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