Characterization of Nitrosocarbonyl Compounds by Neutralization‐Reionization Mass Spectrometry

O'bannon, P. E.; Sülzle, Detlev; Schwarz, Helmut

doi:10.1002/hlca.19910740841

Cited by 11 publications

(10 citation statements)

References 26 publications

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“…The direct spectroscopic observation of acyl nitroso compounds has been accomplished in the gas phase using both charge reversal and neutralization-reionization mass spectrometry [120,121] and more recently in solution using nanosecond timeresolved IR spectroscopy [122].…”

Section: The Intermediacy Of Acyl Nitroso Species In Reactionsmentioning

confidence: 99%

Donors of HNO

Miranda

Nagasawa

Toscano

2005

CTMC

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Recent comparisons of the pharmacological effects of nitric oxide (NO) and nitroxyl (HNO) donors have demonstrated that the responses to these redox-related nitrogen oxides are nearly universally dissimilar. These analyses have suggested the existence of mutually exclusive signaling pathways as a result of discrete chemical interactions of HNO and NO with a variety of critical biomolecules. Although the mechanisms of action are currently unresolved, the pharmacological responses to HNO are promising for clinical treatment of cardiovascular diseases such as heart failure, myocardial infarction and stroke. This review provides a detailed discussion of the most commonly utilized donors of HNO as well as a guideline for the characterization of novel donors.

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Section: The Intermediacy Of Acyl Nitroso Species In Reactionsmentioning

confidence: 99%

Donors of HNO

Miranda

Nagasawa

Toscano

2005

CTMC

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“…Acylnitroso species could not be isolated and W. G. Kirby pointed out that the only evidence for their existence were products 5-7 resulting from nucleophilic attack at the acylnitroso carbonyl 4 (Scheme 2) [2]. The first direct spectroscopic evidence for acylnitroso species came from the work of H. Schwarz et al as they generated these species by retro-Diels-Alder reactions of cycloadducts and were directly detected by neutralization-re-ionization mass spectrometry [8]. Very recently, these species have directly been detected in solution by time-resolved IR spectroscopy [9].…”

Section: Synthesis Of Acylnitroso Intermedia-tesmentioning

confidence: 99%

Synthesis of Acylnitroso Intermediates and Their Synthetic Applications

Iwasa¹,

Fakhruddin²,

Nishiyama³

2005

MROC

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Acylnitroso intermediates are usually known as super reactive species, always prepared in situ and can be readily trapped via hetero-Diels-Alder reactions with dienes or with olefins via ene reactions, which open a magnificent access to produce a variety of complicated and very demanding organic molecules. Both of these reactions of acylnitroso species have been proved as the key synthetic tool in the total synthesis of natural products. The synthetic methods used to prepare these intermediates as well as their recent synthetic applications to the total synthesis of natural products are briefly described in this minireview.

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“…Charge-reversal and neutralization-reionization mass spectrometry experiments provide the first spectroscopic evidence for the existence of acyl nitroso compounds in the gas phase [63,64]. More recently, timeresolved infrared spectroscopic measurements reveal evidence for the first direct observation of an acyl nitroso compound in solution [65].…”

Section: Acyl Nitroso Compounds As Hno Donorsmentioning

confidence: 96%

N-Hydroxyurea and Acyl Nitroso Compounds as Nitroxyl (HNO) and Nitric Oxide (NO) Donors

Sb¹

2005

CTMC

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Hydroxyurea has emerged as a new therapy for sickle cell disease but a complete mechanistic description of its beneficial actions does not exist. Patients taking hydroxyurea show evidence for the in vivo conversion of hydroxyurea to nitric oxide (NO), which also has drawn interest as a sickle cell disease treatment. While the chemical oxidation of hydroxyurea produces NO or NO-related products, NO formation from the reactions of hydroxyurea and hemoglobin do not occur fast enough to account for the observed increases in patients taking hydroxyurea. Both horseradish peroxidase and catalase catalyze the rapid formation of nitric oxide and nitroxyl (HNO) from hydroxyurea. In these reactions, hydroxyurea is converted to an acyl nitroso species that hydrolyzes to form HNO. The ferric heme protein then oxidizes HNO to NO that combines with the heme iron to form a ferrous-NO complex that may act as an NO donor. In general, acyl nitroso compounds, regardless of the method of their preparation, hydrolyze to form HNO and the corresponding carboxylic acid derivative. Similarly, the incubation of blood and hydroxyurea with urease rapidly form NO-related species suggesting the initial urease-mediated hydrolysis of hydroxyurea to hydroxylamine, which then reacts quickly with hemoglobin to form these products. These studies present two NO releasing mechanisms from hydroxyurea that are kinetically competent with clinical observations.

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Characterization of Nitrosocarbonyl Compounds by Neutralization‐Reionization Mass Spectrometry

Abstract: ~~The neutral molecules nitrosoformaldehyde (la), 1-nitrosoacetaldehyde (Ib), and 2,2,2-trifluoro-1-n1troso-acetaldehyde (lc) have been generated and detected by neutralization-reionization mass spectrometry (NR-MS)

Cited by 11 publications

References 26 publications

Donors of HNO

Donors of HNO

Synthesis of Acylnitroso Intermediates and Their Synthetic Applications

N-Hydroxyurea and Acyl Nitroso Compounds as Nitroxyl (HNO) and Nitric Oxide (NO) Donors

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