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Theoretical Study on Proton‐Transfer Reaction of Intracellular Second‐messenger 3′,5′‐Cyclic Nucleotide
Author(s) -
ZHANG AiHua,
YANG BaoHua,
LI ZongHe
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890248
Subject(s) - chemistry , molecule , nucleotide , proton , intracellular , water gas shift reaction , catalysis , reaction mechanism , second messenger system , gas phase , stereochemistry , computational chemistry , photochemistry , organic chemistry , biochemistry , physics , quantum mechanics , gene
The gas‐phase proton‐transfer reaction mechanism of intracellular second‐messenger 3′,5′‐cyclic nucleotide (cAMPm) has been theoretically investigated at the B3LYP/6‐31G∗ ∗ level. One or two H 2 O molecules have been used to simulate the catalyst. It is found that H shift reaction between conformation Bm and conformation Dm of cAMPm involves a cyclic transition state with one or two water molecules as a shuttle. Furthermore, H shift reaction proceeds easily with the participation of two water molecules. The results provide evidence in theory to study proton‐transfer reaction mechanism of related phosphodiesters. Our present calculations have rationalized all the possible reaction channels.