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Hydrolytic reactions of cyclic bis(3′‐5′)diadenylic acid (c‐di‐AMP)
Author(s) -
Ora Mikko,
Martikainen Kaisa,
Lautkoski Kristian
Publication year - 2013
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3070
Subject(s) - chemistry , depurination , hydrolysis , isomerization , high performance liquid chromatography , glycosidic bond , bond cleavage , adenosine monophosphate , adenosine , cleavage (geology) , medicinal chemistry , stereochemistry , organic chemistry , enzyme , catalysis , biochemistry , dna , geotechnical engineering , fracture (geology) , engineering
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 °C. Under neutral and basic conditions (pH ≥ 7), 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 H 0 = −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 1–3, isomerization to cyclic bis(2′‐5′)diadenylic acid competes with the depurination. Copyright © 2012 John Wiley & Sons, Ltd.