S. Nomoto et al., UNDER-FLAME REACTION OF SULFUR-CONTAINING AMINO-ACIDS BY A HYDROGEN-OXYGEN FLAME, Bioscience, biotechnology, and biochemistry, 62(4), 1998, pp. 643-649
Methionine was subjected to a flame-induced reaction in water or in an
aqueous formic acid solution by using a hydrogen (50%)-oxygen (50%),
hydrogen (87%)-oxygen (13%) and hydrogen diffusion flame. Besides the
already-known stepwise oxidation by a hydroxyl radical, the contributi
on of a hydrogen atom from the flame to the reaction was recognized wh
en the hydrogen-rich mixtures were employed. Homoserine was obtained u
nder all the reaction conditions employed here, and glutamic acid when
employing aqueous formic acid as a solvent. A common intermediate, th
e 3-carboxy-3-aminopropyl radical, appeared to exist in the reaction p
athway. A coupling reaction of this radical with a hydrogen atom, hydr
oxyl radical and hydroxycarbonyl radical afforded 2-aminobutyric acid,
homoserine and glutamic acid, respectively. Lanthionine and S-methylc
ysteine underwent the same reactions. Increasing the hydrogen content
of the fuel and adding formic acid to the solvent resulted in retardin
g the reaction rate. The latter modification of the reaction system al
so brought about greater stability of the reaction products.