Reversible fluorescence derivatization of amino groups using dansylaminomethylmaleic acid via its anhydride

Kayo Sakata, Kenji Hamase, Shigeki Sasaki, Minoru Maeda, Kiyoshi Zaitsu

Research output: Contribution to journalArticle

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Abstract

A new derivatizing reagent, dansylaminomethylmaleic acid (DAM), was synthesized and utilized for the reversible fluorescence labeling of amino groups. The reagent DAM was dehydrated in the presence of (trimethylsilyl)ethoxyacetylene, a dehydrating agent, and the resulting anhydride reacted with amino groups, and could then be liberated under mild acidic conditions. With this reagent, benzylamine was derivatized as a model amino compound. The resultant fluorescent derivative, N-benzyl-2- dansylaminomethylmaleamic acid (BDAM), could be detected at 520 nm with fluorescence excitation at 340 nm. The fluorescence detection limit of BDAM (100 fmol, S/N=3)was smaller than that of intact benzylamine (200 pmol, S/N=10, absorbance at 254 nm). Under mild acidic conditions of pH 5.0, 82% of benzylamine was regenerated from BDAM within a day. With this reagent, insulin was successfully derivatized and 56% of insulin was regenerated.

Original languageEnglish
Pages (from-to)1095-1099
Number of pages5
Journalanalytical sciences
Volume15
Issue number11
DOIs
Publication statusPublished - Jan 1 1999

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Anhydrides
Fluorescence
Acids
Insulin
Labeling
Derivatives
benzylamine

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry

Cite this

Reversible fluorescence derivatization of amino groups using dansylaminomethylmaleic acid via its anhydride. / Sakata, Kayo; Hamase, Kenji; Sasaki, Shigeki; Maeda, Minoru; Zaitsu, Kiyoshi.

In: analytical sciences, Vol. 15, No. 11, 01.01.1999, p. 1095-1099.

Research output: Contribution to journalArticle

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abstract = "A new derivatizing reagent, dansylaminomethylmaleic acid (DAM), was synthesized and utilized for the reversible fluorescence labeling of amino groups. The reagent DAM was dehydrated in the presence of (trimethylsilyl)ethoxyacetylene, a dehydrating agent, and the resulting anhydride reacted with amino groups, and could then be liberated under mild acidic conditions. With this reagent, benzylamine was derivatized as a model amino compound. The resultant fluorescent derivative, N-benzyl-2- dansylaminomethylmaleamic acid (BDAM), could be detected at 520 nm with fluorescence excitation at 340 nm. The fluorescence detection limit of BDAM (100 fmol, S/N=3)was smaller than that of intact benzylamine (200 pmol, S/N=10, absorbance at 254 nm). Under mild acidic conditions of pH 5.0, 82{\%} of benzylamine was regenerated from BDAM within a day. With this reagent, insulin was successfully derivatized and 56{\%} of insulin was regenerated.",
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AU - Hamase, Kenji

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AU - Zaitsu, Kiyoshi

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