E11.1: The beta-phosphate of UTP is attacked by the nucleophilic hydroxyl group, and inorganic phosphate is expelled. This is the first such phosphoryl transfer reaction that we have seen (we have seen the beta-phosphate of ATP attacked by an alcohol in section 10.2C, but that attack was from the 'other side' - it resulted in expulsion of AMP and formation of an organic diphosphate).
a) cycic ketal formation:
b) cyclic ketal hydrolysis:
C11.2: See Biochemistry 1994, 33, 13792, mechanism II.
C11.3: See Biochemistry 2000, 39, 8603.
C11.4: See J. Am. Chem. Soc. 2005, 127, 16412.
C11.5: See J. Biol. Chem. 2010, 285, 18684, fig 5A.
- Organic Chemistry With a Biological Emphasis, Tim Soderberg (University of Minnesota, Morris)