Investigation of hydrolytic deamination of 1-(2-hydroxy-1-phenylethyl)adenosine.
The ring nitrogen of adenosine reacts at both the alpha- (benzylic) and beta-carbons of styrene oxide to form 1-substituted products. The 1-(2-hydroxy-1-phenylethyl)adenosines formed by oxirane ring opening at the alpha-position are prone to an unusually facile hydrolytic deamination. By conducting hydrolysis reactions in [18O]water and analyzing the reaction products by electrospray mass spectrometry, we find that deamination occurs by direct attack of water at the 6-position of the adenine ring system with displacement of the exocyclic amino group.
Barlow
T
T
Chemistry of Carcinogenesis Laboratory, NCI-Frederick Cancer Research and Development Center, Maryland 21702, USA. barlowt@ncifcrf.gov
Ding
J
J
Vouros
P
P
Dipple
A
A
D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry; D003500:Cyclization; D003641:Deamination; D004852:Epoxy Compounds / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
C110143:1-(2-hydroxy-1-phenylethyl)adenosine; D004852:Epoxy Compounds; C013690:styrene oxide; D000241:Adenosine