Journal of Applied Glycoscience
Online ISSN : 1880-7291
Print ISSN : 1344-7882
ISSN-L : 1344-7882
Regular Paper
Efficient Alkaline Isomerization of Lactose to Lactulose in the Presence of an Organogermanium Compound
Sugar Isomerization with an Organogermanium Compound
Takae Nagasawa Katsuyuki SatoTakafumi Kasumi
Author information
JOURNAL FREE ACCESS FULL-TEXT HTML

2017 Volume 64 Issue 2 Pages 27-32

Details
Abstract

Lactulose, a disaccharide widely used in pharmaceuticals and functional foods, is produced by lactose isomerization. Lactose and lactulose have an aldose–ketose relationship. Less than 25 % conversion of lactose into lactulose is achieved using the Lobry de Bruyn–Alberda van Ekenstein transformation with heating, whereas the conversion is increased to 80 % by the addition of an approximately equimolar concentration of the organogermanium compound 3-(trihydroxygermyl)propanoic acid (THGP) to the reaction mixture. To further understand this phenomenon, in this study, we analyzed the affinity between THGP and sugar isomers using 1H nuclear magnetic resonance spectroscopy. For the dimethyl derivative of THGP with lactose and lactulose, the complex formation ratios at 0.1 M (1:1 mixing ratio) were 14 and 59 %, respectively, with complex formation constants of 1.8 and 43 M–1, respectively. The complex formation capacity was approximately 24-fold higher for lactulose than for lactose. Moreover, THGP is considered to protect lactulose from alkaline degradation, resulting in high production yield of lactulose. Therefore, we concluded that high affinity for the isomerization product may promote isomerization and that promotion of sugar isomerization using an organogermanium compound is an effective method for converting lactose to lactulose.

Content from these authors
© 2017 by The Japanese Society of Applied Glycoscience
Previous article Next article
feedback
Top