A1 Refereed original research article in a scientific journal
Hydrolytic reactions of cyclic bis(3 '-5 ')diadenylic acid (c-di-AMP)
Authors: Ora M, Martikainen K, Lautkoski K
Publisher: WILEY-BLACKWELL
Publication year: 2013
Journal: Journal of Physical Organic Chemistry
Journal name in source: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
Journal acronym: J PHYS ORG CHEM
Number in series: 3
Volume: 26
Issue: 3
First page : 218
Last page: 225
Number of pages: 8
ISSN: 0894-3230
DOI: https://doi.org/10.1002/poc.3070(external)
Abstract
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.
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.
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