Volume 87 Issue 24 | p. 26 | Concentrates
Issue Date: June 15, 2009

HNO Generates Unique Chemical Markers

Nitroxyl reacts with organic phosphines, yielding unique amide products that can be used to detect the biologically active nitrogen oxide
Department: Science & Technology
Keywords: nitroxyl, HNO, nitric oxide, congestive heart failure

The first reaction of nitroxyl (HNO) with organic phosphines has been achieved, yielding unique HNO-based amide products that can be used to detect HNO in biological systems (Org. Lett., DOI: 10.1021/ol900914s). HNO, the reduced protonated form of the biological signaling agent nitric oxide, promotes heart contractions and is therefore considered to be the basis for potential congestive heart failure medications. But "the lack of specific HNO detection methods has impeded the understanding of HNO in biological systems," write S. Bruce King and coworkers of Wake Forest University. They report that HNO reacts with triarylphosphines to produce reactive aza-ylides, which then react immediately with a neighboring ester group to generate stable and unique amide products. The amides can thus be used as markers for HNO in biological systems. According to the researchers, these experiments document the reactivity of HNO with triarylphosphines and provide insight into a new method for distinguishing this important biologically active nitrogen oxide.

 
Chemical & Engineering News
ISSN 0009-2347
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