High-Performance Liquid Chromatographic Determination of Amino Acids and Oligopeptides by Pre-column Fluorescence Derivatization with 9-Fluorenyl-methoxy Carbonyl Succinimide

You, Jing; Fan, Xingjun; Wang, Hong‐En; Wang, Guojun; Su, Ji Xin; Zhou, Chunming

doi:10.1080/10826079808006611

Cited by 10 publications

(3 citation statements)

References 19 publications

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“…In general, they do not react with aromatic amines, phenols, or alcohols [4]. Some fluorescent or chromogenic succinimidyl esters have been reported for amine derivatization, such as succinimido phenylcarbamate (SIPC) [5], succinimido p-bromophenylcarbamate (SIBr-PC) [5], succinimido 1-naphthylcarbamate (SINC) [5], 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) [6 -9], N-hydroxysuccinimidyl-a-naphthylacetate (SINA) [10], N-hydroxysuccinimidyl-3-indolyl acetate (SIIA) [11], N-hydroxysuccinimicyl-a-(9-phenanthrene)-acetate (HSMPA) [12], 9-fluorenylmethoxy carbonyl succinimide (Fmoc-OSu) [13], N-hydroxysuccinomodyl-a-(9-acridine)-acetate (HSAA) [14], 5-carboxyfluorescein succinimidyl ester (CFSE) [15], Nhydroxysuccinimidyl fluorescein-O-acetate (SIFA) [16], and N-hydroxysuccinimidyl 4,3,29-naphthapyrone-4-acetate (NPA-OSu) [17], etc. Also, 4-(6,7-dihydro-5,8-dioxothiazolo(4,5-g)phthalazin-2-yl)benzoic acid N-hydroxysuccinimide ester (TPB-Suc) has been used as a highly sensitive chemiluminescence derivatizing reagent for amines in LC [18].…”

Section: Introductionmentioning

confidence: 99%

2,6-Dimethyl-4-quinolinecarboxylic acidN-hydroxysuccinimide ester: A fluorogenic hydrophilic derivatizing reagent for liquid chromatographic analysis of aliphatic amines

et al. 2006

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The use of a fluorogenic, hydrophilic, and amine-reactive reagent, 2,6-dimethyl-4-quinolinecarboxylic acid N-hydroxysuccinimide ester (DMQC-OSu) has been investigated in the procolumn derivatization for the LC separation of aliphatic amines. In pH 8.0 aqueous medium, DMQC-OSu reacted with amines at 50 degrees C within 20 min to form highly fluorescent carboxamides and the excess reagent hydrolyzed to the corresponding carboxylic acid. The separation of representative amine derivatives with DMQC-OSu has been performed using a C18 column with the fluorescence detection at 326/409 nm. The detection limits reached nanomolar level. The proposed method has been applied to the analysis of real samples with recoveries of 94-108%. Compared with other succinimidyl esters used in the derivatization of amino compounds, DMQC-OSu and its hydrolysate had negligible fluorescence (phi(fl) = 0.09 and 0.02, respectively), which implied that small peaks appeared in chromatograms and slight interference was introduced to the determination.

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Section: Introductionmentioning

confidence: 99%

2,6-Dimethyl-4-quinolinecarboxylic acidN-hydroxysuccinimide ester: A fluorogenic hydrophilic derivatizing reagent for liquid chromatographic analysis of aliphatic amines

et al. 2006

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“…A variety of succinimidyl ester reagents with fluorophores or chromophores have recently been developed and used as labeling reagents for amino compounds in high-performance liquid chromatography (HPLC) with absorbance or fluorescence detection; examples include 6-aminoquinolyl-N-hydroxysuccinmidyl carbamate (AQC) [1 31, 9-fluorenylmethoxy carbonyl succinimide (Fmoc-OSu) [4], N-hydroxysuccinimidyl-c~-(9-phenanthrene) acetate [5], and N-hydroxysuccinimidyl-3-indolyl acetate (SIIA) [6]. These reagents react readily with amines under mild conditions to give stable amine conjugates without forming by-products.…”

Section: Introductionmentioning

confidence: 99%

4:3-β-naphthapyrone-4-acetic acidN-hydroxysuccinimidyl ester as a fluorescent labeling reagent for amino acids and oligopeptides in high-performance liquid chromatography

et al. 2001

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KeyWordsColumn liquid chromatography 4:3-fl-Naphthapyrone-4-acetic acid N-hydroxysuccinimidyl ester (NPA-OSu) Amino acid Oligopeptide Fluorescent derivatizing reagent Summary 4:3-~-Naphthapyrone-4-acetic acid N-hydroxysuccinimidyl ester (NPA-OSu) is a highly sensitive and moderately reactive derivatizing reagent with a naphthapyrone moiety as fluorophore and an N-hydroxysuccinimidyl active ester as reactive group toward amino compounds. It is readily prepared in lvvo steps. The fluorescence properties of NPA-OSu and its hydrolysis product have been studied in detail, and the conditions for derivatization and separation of the NPA-OSu derivatives of some amino acids and oligopeptides have been investigated. At 2ex = 352 nm and ~em = 422 nm the detection limits (signal-to-noise ratio = 3) for amino acids and oligopeptides reached frnol levels for injection of 20 gL; this sensitivity was comparable with that obtained by use of 7-(diethylamino)coumarin-3-carboxylic acid succinimidyl ester as derivatizing reagent in the analysis of amino acids by capillary electrophoresis with laser-induced-fluorescence detection.

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“…During reaction with amino groups, the excess of the reagents is hydrolyzed to the corresponding carboxylic acids. Recently, some reagents with the substituent of N-hydroxysuccinimidyl ester have been reported as the derivatizing reagents in the determination of amino acids and peptides by chromatographic methods (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13), such as 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) (1-7), N-hydroxysuccinimidyl-3-indolylacetate (SIIA) (9), and N-hydroxysuccinimidyl-α-(9-acridine)-acetate (HSAA) (13). These kinds of reagents provide ideal candidates for the analysis of amino acids and peptides.…”

Section: Introductionmentioning

confidence: 99%

N-Hydroxysuccinimidyl-Fluorescein-O-Acetate for Precolumn Fluorescence Derivatization of Amino Acids and Oligopeptides in Liquid Chromatography

Wang

Jin

Yang

et al. 2001

Journal of Chromatographic Science

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A new fluorescent derivatizing reagent, N-hydroxysuccinimidyl-fluorescein-O-acetate, is used for the high-performance liquid chromatographic analysis of amino acids and oligopeptides. This reagent has the advantages of high-detection sensitivity in the visible region, specifically with amino groups, mild derivatization conditions, and little interference induced. The fluorescence properties of the reagent and its derivatives with amino acids and oligopeptides are studied. The conditions of the derivatization are investigated in detail. In the mobile phase of methanol-water (42:58, v/v) containing a 10 mM pH 5.0 citric acid-Na2HPO4 buffer, six amino acids and oligopeptides are separated in 20 min with fluorescence detection at excitation and emission wavelengths of 492 and 513 nm, respectively, with the detection limits for injected standards ranging from 0.64 to 12 fmol.

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High-Performance Liquid Chromatographic Determination of Amino Acids and Oligopeptides by Pre-column Fluorescence Derivatization with 9-Fluorenyl-methoxy Carbonyl Succinimide

Cited by 10 publications

References 19 publications

2,6-Dimethyl-4-quinolinecarboxylic acidN-hydroxysuccinimide ester: A fluorogenic hydrophilic derivatizing reagent for liquid chromatographic analysis of aliphatic amines

2,6-Dimethyl-4-quinolinecarboxylic acidN-hydroxysuccinimide ester: A fluorogenic hydrophilic derivatizing reagent for liquid chromatographic analysis of aliphatic amines

4:3-β-naphthapyrone-4-acetic acidN-hydroxysuccinimidyl ester as a fluorescent labeling reagent for amino acids and oligopeptides in high-performance liquid chromatography

N-Hydroxysuccinimidyl-Fluorescein-O-Acetate for Precolumn Fluorescence Derivatization of Amino Acids and Oligopeptides in Liquid Chromatography

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