Nucleophilic addition to the 9 position of 9‐phenylcarboxylate‐10‐methylacridinium protects against hydrolysis of the ester
作者:
Philip W. Hammond,
Wendy A. Wiese,
Alex A. Waldrop,
Norman C. Nelson,
Lyle J. Arnold,
期刊:
Journal of Bioluminescence and Chemiluminescence
(WILEY Available online 1991)
卷期:
Volume 6,
issue 1
页码: 35-43
ISSN:0884-3996
年代: 1991
DOI:10.1002/bio.1170060108
出版商: John Wiley&Sons, Ltd.
关键词: Acridinium ester;chemiluminescence;DNA probes;ester protection;nucleophilic addition
数据来源: WILEY
摘要:
AbstractThe chemiluminescent reaction of an acridinium ester (AE) requires addition of peroxide to the 9 position of the acridinium ring. The addition of a hydroxide ion to the 9 position of an acridinium ester to form the carbinol adduct has also been well documented. We have observed a similar addition of other nucleophiles to the acridinium ring to form an acridan adduct. The adduct formed with bisulphite has been particularly well‐characterized for rate of formation, rate of reversion, and reaction equilibrium. The formation of an adduct (other than H2O2) has been demonstrated to decrease significantly the reactivity of the adjacent ester bond to alkaline hydrolysis. The resulting, more stable adduct is very useful when the acridinium ester is used as a label in DNA probe‐based assays. The adduct is highly resistant to hydrolysis under the conditions often desired for DNA probe‐based assays (high temperature, elevated pH, extended sto
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