Detection of DBD-Carbamoyl Amino Acids in Amino Acid Sequence and Configuration Determination of Peptides with Fluorogenic Edman Reagent 7-[(N,N-Dimethylamino)sulfonyl]-2,1,3- benzoxadiazol-4-yl Isothiocyanate

Huang, Yong; Matsunaga, Hirokazu; Toriba, Akira; Santa, Tomofumi; Fukushima, Takeshi; Imai, Kazuhiro

doi:10.1006/abio.1999.4031

Cited by 14 publications

(12 citation statements)

References 30 publications

(34 reference statements)

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“…DBD-TC-Pro was prepared by coupling DBD-NCS (20 mM Â 10 mL) with free proline in 50% pyridine at 50°C for 15 min and dried with a centrifugal evaporator at 50°C for 15 min. The oxidation of DBD-TC-Pro was carried out in the same conditions as previously described (Huang et al, 1999). Briefly, the DBD-TC-Pro dissolved in 10 mL of CH 3 CN was added with 5 mL of 4 M HCl and 5 mL of 0.5 M NaNO 2 in water, and reacted at room temperature for 10 min.…”

Section: Methodsmentioning

confidence: 99%

“…These results suggested that the cyclization reaction proceeded preferentially with the minor desulfurized product in the oxidation of DBD-TC-secondary amines with NaNO 2 /H . However, in the oxidation of DBD-TC-primary amines, the desulfurization reaction proceeded preferentially and the cyclized compounds were scarcely observed in the chromatogram (Huang et al, 1999).…”

Section: Identi®cation Of the Reaction Productmentioning

confidence: 97%

“…Although most of DBD-TC-amino acids were oxidized to the corresponding DBD-CA-amino acids, DBD-TC-Pro was not easily oxidized to DBD-CA-Pro [l max (excitation), 384 nm; l max (emission), 520 nm in acetonitrile/water], and instead converted to another unidentified fluorescent compound [l max (excitation), 440 nm; l max (emission), 575 nm in acetonitrile/water] (Huang et al, 1999). In this paper, we will describe the structure of the compound, and discuss the reaction mechanism of DBD-TC-amines with NaNO 2 /H .…”

Section: Introductionmentioning

confidence: 99%

“…In previous papers we have established a modified Edman procedure using the fluorogenic Edman reagent,1, isothiocyanate (DBD-NCS) (Uzu et al, 1993;Matsunaga et al, 1995), in which the liberated DBD-TZ-amino acids were hydrolyzed to DBD-thiocarbamoyl (TC)-amino acids, followed by the oxidation with NaNO 2 /H to the corresponding DBD-carbamoyl (CA)-amino acids, and thus the generated DBD-CA-amino acids were fluorometrically detected (Huang et al, 1999). Although most of DBD-TC-amino acids were oxidized to the corresponding DBD-CA-amino acids, DBD-TC-Pro was not easily oxidized to DBD-CA-Pro [l max (excitation), 384 nm; l max (emission), 520 nm in acetonitrile/water], and instead converted to another unidentified fluorescent compound [l max (excitation), 440 nm; l max (emission), 575 nm in acetonitrile/water] (Huang et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

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Fluorescent oxidation products derived from DBD-thiocarbamoyl amino acid in the modified Edman sequencing analysis

Huang

Santa

Uchiyama

et al. 2000

Biomed. Chromatogr.

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Section: Methodsmentioning

confidence: 99%

Section: Identi®cation Of the Reaction Productmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Fluorescent oxidation products derived from DBD-thiocarbamoyl amino acid in the modified Edman sequencing analysis

Huang

Santa

Uchiyama

et al. 2000

Biomed. Chromatogr.

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“…26 A mixture of the corresponding amine sample (2.0 µmol), KAP-NH01 (2.0 µmol) and a base in ethanol (100 µl) was stirred at room temperature for 20 min in a screw-capped vial. After the reaction, the solvent was removed under a nitrogen stream, and the residue was dissolved in methanol to measure the mass spectra.…”

Section: Derivatization Of Primary Amine Compounds Using Kap-nh01mentioning

confidence: 99%

Design and Synthesis of Labeling Reagents (MS Probes) for Highly Sensitive Electrospray Ionization Mass Spectrometry and Their Application to the Detection of Carbonyl, Alcohol, Carboxylic Acid and Primary Amine Samples

et al. 2004

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Liquid-MS systems, including liquid chromatography-MS instruments (LC/MS), have been used as the most promising qualitative and quantitative analytical methods for a number of substances, including nonvolatile or high molecular-weight substances. [1][2][3][4][5] In this context, electrospray ionization (ESI) is rapidly developing as a method for producing gas-phase ions from analyte species in solution for subsequent analysis by mass spectrometry. The combination of ESI with mass spectrometry, first demonstrated by Fenn and co-workers, 6 has proven to be useful in the analysis of nonvolatile, polar and thermally labile compounds, especially in high-molecular-weight biopolymer analysis, in large part (peptides, proteins, DNA) because these analytes give multi-charged molecular ions, which are observed in the modest m/z range (i.e., m/z < 4000) in mass analyzers. [7][8][9][10][11] However, not all analytes are suitable for ESI-MS measurements due to limitations in the transfer of analytes from solution to the gas phase as ions via the electrospray ionization process. 12-14In order to achieve effective ionization of the sample analyte to be detected by an ESI-MS system, a protic solvent acting via Brφnsted or Lewis acid chemistry (formic acid, acetic acid, trifluoroacetic acid, etc.) or an inorganic salt (ammonium acetate, sodium salt, potassium salt, etc.) is often added to the mobile phase (methanol, water and acetonitrile, etc.) to produce an ionic species [M+H] + , a molecular ion with a proton. However, these solvents and salt additives often result in poor ionization for neutral and nonpolar molecules, and cause problems in the ESI-MS system, such as the following: [15][16][17] i) In the positive ion MS mode, an acid additive such as trifluoroacetic acid lowers the sensitivity due to pairing of the Novel labeling reagents, called MS probes, which possess a positively charged quaternary amine moiety and can transform a neutral analyte into a charged compound by simply mixing with the analyte and allowing the mixture to stand from several minutes to 30 min at room temperature or while heating to 50˚C, were designed and synthesized for the highly sensitive detection of carbonyl, alcohol, carboxylic acid and primary amine samples by electrospray ionization mass spectrometry (ESI-MS). The positively charged products can be detected with high sensitivity in an ESI-MS system, which is the most popular liquid MS instrument. All of the labeled products showed a remarkably large increase in the molecular-ion peak abundance detection sensitivity of over 500-fold at picomolar concentration levels compared to that of unlabeled analytes in an ESI-MS system. These MS probes, used together with liquid MS detection, are widely applicable as a convenient method for the highly sensitive detection of less than picomolar levels of analytes, and therefore greatly enhance the power of ESI-MS analysis.

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Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

Uchiyama

Santa

Okiyama

et al. 2001

Biomedical Chromatography

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151

101

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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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Detection of DBD-Carbamoyl Amino Acids in Amino Acid Sequence and Configuration Determination of Peptides with Fluorogenic Edman Reagent 7-[(N,N-Dimethylamino)sulfonyl]-2,1,3- benzoxadiazol-4-yl Isothiocyanate

Cited by 14 publications

References 30 publications

Fluorescent oxidation products derived from DBD-thiocarbamoyl amino acid in the modified Edman sequencing analysis

Fluorescent oxidation products derived from DBD-thiocarbamoyl amino acid in the modified Edman sequencing analysis

Design and Synthesis of Labeling Reagents (MS Probes) for Highly Sensitive Electrospray Ionization Mass Spectrometry and Their Application to the Detection of Carbonyl, Alcohol, Carboxylic Acid and Primary Amine Samples

Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

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