<i>N</i>-Methyl-4-hydrazino-7-nitrobenzofurazan as a New Reagent for Air Monitoring of Aldehydes and Ketones

Büldt, Andrea; Kärst, Uwe

doi:10.1021/ac980946f

Cited by 50 publications

(50 citation statements)

References 17 publications

(28 reference statements)

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“…In our study, a single and intense fragment ion at m/z 151 was observed in the product ion spectra, which might be favorable for the detection in MRM. Although the attained detection limits in this study were comparable to those obtained with cyclohexanediones or a little less sensitive than those obtained with 4-(N,N-dimethylaminosulfonyl)-7-hydrazino-2,1,3-benzoxadiazole (DBD-H) and 4-aminosulfonyl-7-hydrazino-2,1,3-benzoxadiazole (ABD-H) (Uzu et al, 1990) for fluorescent detection, and N-methyl-4-hydrazino-7-nitrobenzofurazan (MNBDH) (Buldt and Karst, 1999) and 4-(N,N-dimethylaminosulfonyl)-7-Nmethylhydrazino-2,1,3-benzoxadiazole (MDBDH) (Jackmann and Karst, 2001) for ultraviolet/visible detection. Hydrazino or methylhydrazino groups were appropriate as the reaction group for aldehydes, since these reagents reacted with aldehydes rapidly under mild conditions.…”

Section: Resultssupporting

confidence: 79%

Synthesis of 4‐[2‐(N,N‐dimethylamino)ethylaminosulfonyl]‐7‐N‐methylhydrazino‐2,1,3‐benzoxadiazole (DAABD‐MHz) as a derivatization reagent for aldehydes in liquid chromatography/electrospray ionization–tandem mass spectrometry

Santa

Al-Dirbashi

Ichibangase

et al. 2007

Biomedical Chromatography

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Benzofurazan derivatization reagent, 4-[2-(N,N-dimethylamino)ethylaminosulfonyl]-7-N-methylhydrazino-2,1,3-benzoxadiazole (DAABD-MHz), for aldehydes in liquid chromatography/electrospray ionization-tandem mass spectrometry (LC/ESI-MS/MS), was synthesized. DAABD-MHz reacted with aliphatic aldehydes under mild conditions. The generated derivatives were separated on a reversed-phase column and detected by ESI-MS/MS with detection limits of 30-60 fmol on-column. Upon collision-induced dissociation, a single and intense fragment ion at m/z 151 was observed. These results suggested that DAABD-MHz was suitable as a derivatization reagent in LC/ESI-MS/MS.

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Section: Resultssupporting

confidence: 79%

Synthesis of 4‐[2‐(N,N‐dimethylamino)ethylaminosulfonyl]‐7‐N‐methylhydrazino‐2,1,3‐benzoxadiazole (DAABD‐MHz) as a derivatization reagent for aldehydes in liquid chromatography/electrospray ionization–tandem mass spectrometry

Santa

Al-Dirbashi

Ichibangase

et al. 2007

Biomedical Chromatography

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“…560 nm). MNBDH was converted to fluorescent N-methyl-4-amino-7-nitro-2,1,3-benzoxadiazole by the reaction with ozone or nitrogen dioxide (Büldt and Karst, 1999a). The detemination of nitrite using MNBDH was also reported (Büldt and Karst, 1999b).…”

Section: For Carboxylic Acids Nbd-pzmentioning

confidence: 99%

Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

Uchiyama

Santa

Okiyama

et al. 2001

Biomedical Chromatography

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Fluorogenic and fluorescent labeling reagents having a benzofurazan (2,1,3-benzoxadiazole) skeleton such as 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F), 4-N,N-dimethylaminosulfonyl-7-fluoro-2,1,3-benzoxadiazole (DBD-F), 4-aminosulfonyl-7-fluoro-2,1,3-benzoxadiazole (ABD-F), ammonium 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate (SBD-F), 4-hydrazino-7-nitro-2,1,3-benzoxadiazole (NBD-H), 4-N,N-dimethylaminosulfonyl-7-hydrazino-2,1,3-benzoxadiazole (DBD-H), 4-nitro-7-N-piperazino-2,1,3-benzoxadiazole (NBD-PZ), 4-N,N-dimethylaminosulfonyl-7-N-piperazino-2,1,3-benzoxadiazole (DBD-PZ), 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole (DBD-COCl) and 7-N,N-dimethylaminosulfonyl-4-(2,1,3-benzoxadiazolyl) isothiocyanate (DBD-NCS) are reviewed in terms of synthetic method, reactivity, fluorescence characteristics, sensitivity and application to analytes.

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“…To test the reactions with 2, we selected two arylhydrazines (3 and 4) that are commonly used as aldehyde-specific dyes. [12,13] The reactions of aldehydenucleotide 2 with 3 or 4 proceeded at room temperature for approximately 20 hours and gave the corresponding orange (5) or violet (6) hydrazones, which were fully characterized (see the Supporting Information). As the formation of hydrazone in water is inherently a reversible reaction, the yields for the isolated products of 51 and 31 %, respectively, were acceptable and useful.…”

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confidence: 99%

Direct Polymerase Synthesis of Reactive Aldehyde‐Functionalized DNA and Its Conjugation and Staining with Hydrazines

et al. 2010

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Apart from a wide range of novel applications of functionalized DNA in chemical biology, nanotechnology, and material sciences, [1] attachment of reactive functional groups to nucleic acids is needed for further transformations or bioconjugates. The introduction of alkyne, azide, or diene groups either by chemical phosphoramidite synthesis or by enzymatic polymerase synthesis has been achieved and the modified DNA was used for click-chemistry, [2,3] Staudinger ligation, [4] and Diels-Alder reactions.[5] An aldehyde functional group is a very attractive group because of its high and specific reactivity with diverse reagents. However, it was considered too reactive and fragile to be incorporated directly (chemically or enzymatically) [6] and the few successful examples were prepared indirectly by a click reaction with azide derivatives of reducing sugars, [3] or by introduction of 2,3-dihydroxypropyl or 3,4-dihydroxypyrrolidine moieties [7,8] and subsequent oxidative cleavage of the vicinal diols to (di)aldehydes. The syntheses of the nucleoside/nucleotide monomers were laborious multistep procedures and additional post-synthetic steps were required to release the aldehyde function in DNA. [7,8] Metallization [7] or interstrand cross-linking [8] were demonstrated to be very useful applications of aldehyde-modified oligonucleotides (ONs) or DNA. Therefore we decided to develop a simple and efficient direct protocol for construction of aldehyde-modified DNA by application of our two-step (cross-coupling polymerase incorporation) method. [9,10] In addition, we wished to develop a methodology for additional conjugation and staining of aldehyde-modified DNA by hydrazone formation.The methodology of choice involved Suzuki cross-coupling of a halogenated nucleoside triphosphate (dNTP) with an aldehyde-containing boronic acid, and subsequent polymerase incorporation into DNA.[9, 10] Furthermore, we wanted to develop a general methodology for hydrazone formation in aqueous media. To test the first and last steps of our proposed route, we performed the reactions on the model compound 5-iodo-dCMP (1; dCMP = 2'-deoxycytidine-5'-O-monophosphate). Commercially available 5-formylthiophene-2-boronic acid was selected as a suitable carrier for the aldehyde group, and its aqueous-phase cross-coupling with monophosphate 1 proceeded within 40 minutes and gave aldehyde-modified dCMP 2 in 50 % yield (Scheme 1). The next task was the formation of the hydrazone species, which is usually only performed in dry organic solvents (owing to the formation of water in the reaction). To make the reaction amenable to aqueous conditions, we have adapted the protocol developed by Dawson and co-workers [11] for aqueous conjugation of peptides, which uses aqueous ammonium acetate and aniline to facilitate the condensation. To test the reactions with 2, we selected two arylhydrazines (3 and 4) that are commonly used as aldehyde-specific dyes. [12,13] The reactions of aldehydenucleotide 2 with 3 or 4 proceeded at room temperature for approximately 20 ho...

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N-Methyl-4-hydrazino-7-nitrobenzofurazan as a New Reagent for Air Monitoring of Aldehydes and Ketones

Cited by 50 publications

References 17 publications

Synthesis of 4‐[2‐(N,N‐dimethylamino)ethylaminosulfonyl]‐7‐N‐methylhydrazino‐2,1,3‐benzoxadiazole (DAABD‐MHz) as a derivatization reagent for aldehydes in liquid chromatography/electrospray ionization–tandem mass spectrometry

Synthesis of 4‐[2‐(N,N‐dimethylamino)ethylaminosulfonyl]‐7‐N‐methylhydrazino‐2,1,3‐benzoxadiazole (DAABD‐MHz) as a derivatization reagent for aldehydes in liquid chromatography/electrospray ionization–tandem mass spectrometry

Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

Direct Polymerase Synthesis of Reactive Aldehyde‐Functionalized DNA and Its Conjugation and Staining with Hydrazines

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