Using molecular iodine in direct oxidative condensation of aldoses with diamines: an improved synthesis of aldo-benzimidazoles and aldo-naphthimidazoles for carbohydrate analysis.
A practical method has been developed for conversion of unprotected and unmodified aldoses to aldo-benzimidazoles and aldo-naphthimidazoles. Using iodine as an oxidant or promoter in acetic acid solution, a series of mono-, di-, and trialdoses, including those containing carboxyl and acetamido groups, undergo an oxidative condensation reaction with o-phenylenediamine or 2,3-naphthalenediamine at room temperature to give the aldo-benzimidazole and aldo-naphthimidazole products in high yields. No cleavage of the glycosidic bond occurs under such mild reaction conditions. The composition analysis of saccharides is realized by the HPLC analysis of the fluorescent naphthimidazole derivatives.
Lin
Chunchi
C
The Genomics Research Center, Academia Sinica, Taipei, Taiwan.
Lai
Po-Ting
PT
Liao
Sylvain Kuo-Shiang
SK
Hung
Wei-Ting
WT
Yang
Wen-Bin
WB
Fang
Jim-Min
JM
D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000032:analysis* / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D001562:Benzimidazoles; D002241:Carbohydrates; D003959:Diamines; D007093:Imidazoles; D007455:Iodine