β-d-Glucosyl and α-d-Galactosyl Yariv Reagents:  Syntheses from p-Nitrophenyl-d-glycosides by Transfer Reduction Using Ammonium Formate

Yariv β-d-glucosyl (4a) and Yariv α-d-galactosyl (4b) reagents are multivalent phenylglycosides. The β-d-glucosyl reagent is considered diagnostic for arabinogalactan proteins (AGPs) to which it can reversibly bind, stain, and precipitate. The α-d-galactosyl reagent does not bind AGPs and is used as...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2004-12, Vol.52 (25), p.7453-7456
Main Authors: Basile, Dominick V, Ganjian, Iraj
Format: Article
Language:English
Subjects:
ammonium formate
arabinogalactan proteins
arabinogalactans
Biological and medical sciences
chemical analysis
chemical reactions
emulsifiers
Food engineering
Food industries
Formates - chemistry
Fundamental and applied biological sciences. Psychology
General aspects
Glucosides - chemical synthesis
glycoproteins
glycosides
Glycosides - chemistry
Nitrophenols - chemistry
phenolic compounds
Phloroglucinol - analogs & derivatives
Phloroglucinol - chemical synthesis
synthesis
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Summary:Yariv β-d-glucosyl (4a) and Yariv α-d-galactosyl (4b) reagents are multivalent phenylglycosides. The β-d-glucosyl reagent is considered diagnostic for arabinogalactan proteins (AGPs) to which it can reversibly bind, stain, and precipitate. The α-d-galactosyl reagent does not bind AGPs and is used as a control. In a new strategy, we accomplished the large scale synthesis of the Yariv reagents in one continuous step by a transfer reduction method and without a need for any specialized apparatus. As the starting material, p-nitrophenyl-d-glycosides (1) were reduced to p-aminophenyl-d-glycosides (2) using ammonium formate as the hydrogen donor. The excess formate was converted to formic acid and ammonia, which then were removed from the reaction by simple distillation. Without isolation, p-aminophenyl-d-glycosides were diazotized (3) and coupled to phloroglucinol to give the Yariv reagents in ∼40% yield. AGPs are a major component of gum arabic, an emulsifying agent widely used in the food and pharmaceutical industries. Increasing interest in AGPs prompted the development of a relatively easy and inexpensive method for the synthesis of these reagents. Keywords: Yariv reagents; arabinogalactan proteins; ammonium formate; synthesis; transfer reduction
ISSN:0021-8561
1520-5118
DOI:10.1021/jf0401571