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Analysis of the susceptibility of reducing disaccharides composed of d-glucose to glycation using the Maillard reaction and a novel sensitive method that measures the percentage of the open-ring form.

Carbohydrate research (2020-05-16)
Yasuro Shinohara, Yurika Ozawa, Akimi Okita, Koichi Kato, Taku Chiba, Nobuaki Miura, Jun-Ichi Furukawa
ABSTRACT

The susceptibility to glycation of all d-glucose-containing reducing disaccharides (kojibiose, sophorose, nigerose, laminaribiose, maltose, cellobiose, isomaltose, and gentiobiose) was evaluated by Maillard browning and the percentages of their acyclic forms estimated using a novel method to evaluate reactivity toward oxime formation were compared for the first time. This new method is facile and applicable to non-labeled carbohydrates, and it is extremely sensitive, more so than any other previously reported methods. The disaccharides linked by 1-6 bonds displayed both high browning intensity and oxime formation reactivity, and they had the greatest amount of the acyclic form. On the other hand, the proportion of acyclic form was generally very low when glucoses were linked by 1-2, 1-3 and 1-4 bonds. The stability of the 1-3 linkage was drastically reduced when basicity was increased due to β-elimination and the production of a highly reactive dehydrated hexose. The 1-4-linked structures, involved in the formation of amylose and cellulose, respectively, were found to be advantageous due to their relatively low susceptibility to glycation.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Kojibiose, ≥98% (HPLC)
Sigma-Aldrich
D-Altrose, ≥97.0% (HPLC)
Sigma-Aldrich
β-Gentiobiose, ≥85% (remainder primarily α-anomer)
Sigma-Aldrich
D-Allose, 98%
Sigma-Aldrich
3-O-Methyl-D-glucopyranose, ≥98%
Sigma-Aldrich
Maltose solution, BioReagent, for molecular biology, ~20% in H2O
Sigma-Aldrich
L-Rhamnose, natural sourced, 99%, FG