A new pathway to aspartic acid from urea and maleic acid affected by ultraviolet light.
The photochemistry of a mixture of urea and maleic acid, which are thought to have been widely present on the primitive Earth, was studied in order to examine a possibility of the formation of amino acids. When an aqueous solution of urea and maleic acid was irradiated with an ultraviolet light of wavelength 172 nm, urea was revealed to be rather resistant to photochemical decomposition. In contrast, maleic acid was completely decomposed within 4 h, reflecting the reactivity of a C-C double bond in the molecule. In the reaction mixture, 2-isoureidosuccinic acid was detected. The acid was considered to be formed by addition of an isoureido radical which had been produced from urea by the action of a hydroxyl radical, to a C-C double bond of maleic acid. The isoureido group of the product was revealed to undergo thermal rearrangement to afford 2-ureidosuccinic acid (N-carbamoylaspartic acid). The result suggested a novel pathway leading to the formation of aspartic acid from non-amino acid precursors, possibly effected by UV-light on the primitive Earth. The formation of ureidocarboxylic acids is of another significance, since they are capable of undergoing thermal polymerization, resulting in formation of polyamino acids.
Department of Chemistry, University of Tsukuba, Tsukuba 305-8571, Japan.
Masanori
M
Terasaki
Shinya
S
Nomoto
Hajime
H
Mita
Akira
A
Shimoyama
D001224:Aspartic Acid / Q000737:chemistry / Q000528:radiation effects*; D008298:Maleates / Q000737:chemistry* / Q000528:radiation effects; D008958:Models, Molecular; D015394:Molecular Structure; D014466:Ultraviolet Rays; D014508:Urea / Q000737:chemistry* / Q000528:radiation effects
D008298:Maleates; D001224:Aspartic Acid; D014508:Urea; C030272:maleic acid