Reaction of Epichlorohydrin with Adenosine and Uridine- 5′-monophosphates

Abstract

The reaction of epichlorohydrin with 5′-AMP and 5′-UMP in aqueous buffer at pH 5.8 and 37[ddot]C gave two principal products for each nucleotide. These products are characterised as N¹-(3-chloro-2-hydroxypropyl) adenine, 1, 3′-O-(3-chloro-2-hydroxypropyl)-5′-AMP, 2, 3′-O-(3-chloro-2-hydroxypropyl)-5′-UMP, 3; and N³-(3- chloro-2-hydroxypropyl)-5′-UMP, 4, The structure of the products are assigned using UV spectroscopy, ¹H and ¹³C-NMR spectroscopy as well as FAB and high resolution mass spectrometry.