Spirodihydantoin is a minor product of 5-hydroxyisourate in urate oxidation.
[reaction: see text] Spirodihydantoin is a minor product from oxidation of uric acid ( approximately 0.15% yield), while spiroiminodihydantoin is a major product from oxidation of 8-oxo-7,8-dihydroguanine (37% yield, pH 10.2). High pH and temperature favor the formation of both spiro compounds. (18)O labeling experiments and in situ generation and decomposition of 5-hydroxy-N7-methylisouric acid indicate that spirodihydantoin and allantoin and spiroiminodihydantoin and guanidinohydantoin are products of 5-hydroxyisourate and 5-hydroxy-8-oxo-7,8-dihydroguanine intermediates, respectively.
Yu
Hongbin
H
Biological Engineering Division and Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Room 56-731A, Cambridge, Massachusetts 02139, USA.
Niles
Jacquin C
JC
Wishnok
John S
JS
Tannenbaum
Steven R
SR
D002384:Catalysis; D006827:Hydantoins / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D014527:Uric Acid / Q000737:chemistry* / Q000378:metabolism
D006827:Hydantoins; D013141:Spiro Compounds; C504054:spirodihydantoin; D014527:Uric Acid