3-Methoxycarbonyl-5-nitrophenyl boronic acid: high affinity diol recognition at neutral pH

Several boronic acids were screened for their ability to bind to diols. 3-Methoxycarbonyl-5-nitrophenyl boronic acid bound to both a catechol dye as well as fructose with a comparable affinity to that of an ortho-methylamino substituted boronic acid. This work suggests a greater role for appropriate...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2004-01, Vol.14 (1), p.25-27
Hauptverfasser:	Mulla, Hormuzd R., Agard, Nicholas J., Basu, Amit
Format:	Artikel
Sprache:	eng
Schlagworte:	B derivatives Binding Sites Boronic Acids - chemistry Boronic Acids - metabolism Chemistry Exact sciences and technology Fructose - metabolism Hydrogen-Ion Concentration Organic chemistry Organometalloidal and organometallic compounds Preparations and properties
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Zusammenfassung:	Several boronic acids were screened for their ability to bind to diols. 3-Methoxycarbonyl-5-nitrophenyl boronic acid bound to both a catechol dye as well as fructose with a comparable affinity to that of an ortho-methylamino substituted boronic acid. This work suggests a greater role for appropriately functionalized electron deficient boronic acids in diol and carbohydrate recognition. The nitro-boronic acid can be a substitute for the ortho-aminomethyl aryl-boronic acid motif for carbohydrate recognition.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2003.10.017