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A novel electrophilic reagent, 4-(N-chloroformylmethyl-N-methyl)amino- 7-N,N-dimethylaminosulphonyl-2,1,3-benzoxadiazole (DBD-COCl) for fluorometric detection of alcohols, phenols, amines and thiols.
Biomed Chromatogr. 1994 May-Jun; 8(3):107-13.BC

Abstract

A novel electrophilic reagent for alcohols, phenols, amines and thiols, 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulph onyl-2,1,3- benzoxadiazole (DBD-COCl) was synthesized. The reactivity of the reagent to these nucleophiles was studied using high-performance liquid chromatography (HPLC) with precolumn derivatization techniques. DBD-COCl reacted in benzene solution at the room temperature or 60 degrees C with androsterone (a representative of hydroxyls), (-)-mandelic and D,L-lactic acid (hydroxy acid), estrone (phenol), benzylamine (primary amine), phenetidine (aromatic amine) and alpha-mercapto-N,2-naphthylacetamide (thiol) to give fluorescent products bearing fluorescence wavelengths at between 543 nm and 555 nm (excitation at between 437 nm and 445 nm). The base catalyst, quinuclidine was required to complete the reaction with the nucleophiles except aromatic amines. The reaction solution was subjected to a reversed phase HPLC and the detection limits of the derivatives were at the femto mol range on column.

Authors+Show Affiliations

Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

8075519

Citation

Imai, K, et al. "A Novel Electrophilic Reagent, 4-(N-chloroformylmethyl-N-methyl)amino- 7-N,N-dimethylaminosulphonyl-2,1,3-benzoxadiazole (DBD-COCl) for Fluorometric Detection of Alcohols, Phenols, Amines and Thiols." Biomedical Chromatography : BMC, vol. 8, no. 3, 1994, pp. 107-13.
Imai K, Fukushima T, Yokosu H. A novel electrophilic reagent, 4-(N-chloroformylmethyl-N-methyl)amino- 7-N,N-dimethylaminosulphonyl-2,1,3-benzoxadiazole (DBD-COCl) for fluorometric detection of alcohols, phenols, amines and thiols. Biomed Chromatogr. 1994;8(3):107-13.
Imai, K., Fukushima, T., & Yokosu, H. (1994). A novel electrophilic reagent, 4-(N-chloroformylmethyl-N-methyl)amino- 7-N,N-dimethylaminosulphonyl-2,1,3-benzoxadiazole (DBD-COCl) for fluorometric detection of alcohols, phenols, amines and thiols. Biomedical Chromatography : BMC, 8(3), 107-13.
Imai K, Fukushima T, Yokosu H. A Novel Electrophilic Reagent, 4-(N-chloroformylmethyl-N-methyl)amino- 7-N,N-dimethylaminosulphonyl-2,1,3-benzoxadiazole (DBD-COCl) for Fluorometric Detection of Alcohols, Phenols, Amines and Thiols. Biomed Chromatogr. 1994 May-Jun;8(3):107-13. PubMed PMID: 8075519.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A novel electrophilic reagent, 4-(N-chloroformylmethyl-N-methyl)amino- 7-N,N-dimethylaminosulphonyl-2,1,3-benzoxadiazole (DBD-COCl) for fluorometric detection of alcohols, phenols, amines and thiols. AU - Imai,K, AU - Fukushima,T, AU - Yokosu,H, PY - 1994/5/1/pubmed PY - 1994/5/1/medline PY - 1994/5/1/entrez SP - 107 EP - 13 JF - Biomedical chromatography : BMC JO - Biomed Chromatogr VL - 8 IS - 3 N2 - A novel electrophilic reagent for alcohols, phenols, amines and thiols, 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulph onyl-2,1,3- benzoxadiazole (DBD-COCl) was synthesized. The reactivity of the reagent to these nucleophiles was studied using high-performance liquid chromatography (HPLC) with precolumn derivatization techniques. DBD-COCl reacted in benzene solution at the room temperature or 60 degrees C with androsterone (a representative of hydroxyls), (-)-mandelic and D,L-lactic acid (hydroxy acid), estrone (phenol), benzylamine (primary amine), phenetidine (aromatic amine) and alpha-mercapto-N,2-naphthylacetamide (thiol) to give fluorescent products bearing fluorescence wavelengths at between 543 nm and 555 nm (excitation at between 437 nm and 445 nm). The base catalyst, quinuclidine was required to complete the reaction with the nucleophiles except aromatic amines. The reaction solution was subjected to a reversed phase HPLC and the detection limits of the derivatives were at the femto mol range on column. SN - 0269-3879 UR - https://www.unboundmedicine.com/medline/citation/8075519/A_novel_electrophilic_reagent_4__N_chloroformylmethyl_N_methyl_amino__7_NN_dimethylaminosulphonyl_213_benzoxadiazole__DBD_COCl__for_fluorometric_detection_of_alcohols_phenols_amines_and_thiols_ L2 - https://doi.org/10.1002/bmc.1130080303 DB - PRIME DP - Unbound Medicine ER -