Hydrolytic reactions of cyclic bis(3 '-5 ')diadenylic acid (c-di-AMP)

: Ora M, Martikainen K, Lautkoski K

Publisher: WILEY-BLACKWELL

: 2013

: Journal of Physical Organic Chemistry

: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY

: J PHYS ORG CHEM

: 3

: 26

: 3

: 218

: 225

: 8

: 0894-3230

DOI: https://doi.org/10.1002/poc.3070(external)

Hydrolytic reactions of cyclic bis(3-5)diadenylic acid (c-di-AMP) have been followed by Reversed phase high performance liquid chromatography (RP-HPLC) over a wide pH range at 90 degrees C. Under neutral and basic conditions (pH7), disappearance of the starting material (first-order in [OH]) was accompanied by formation of a mixture of adenosine 2-monophosphate and 3-monophosphate (2-AMP and 3-AMP). Under very acidic conditions (from H0=0.7 to 0.2), c-di-AMP undergoes two parallel reactions (first-order in [H+]): the starting material is cleaved to 2-AMP and 3-AMP and depurinated to adenine (i.e., cleavage of the N-glycosidic bond), the former reaction being slightly faster than the latter one. At pH 13, isomerization to cyclic bis(2-5)diadenylic acid competes with the depurination. Copyright (c) 2012 John Wiley & Sons, Ltd.