If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.



Glucose To Sorbose In A Single Step

Acidic zeolite mediates simplified and stereospecific sugar isomerization

by Mitch Jacoby
June 3, 2013 | A version of this story appeared in Volume 91, Issue 22

A Ti-doped zeolite catalyzes this isomerization via a C5-C1 hydride shift.
Reaction scheme shows a Ti-doped zeolite catalyzing an isomierization via a C5-C1 hydride shift.
A Ti-doped zeolite catalyzes this isomerization via a C5-C1 hydride shift.

Some 100,000 tons of l-ascorbic acid (vitamin C) are produced annually worldwide from d-glucose by way of l-sorbose intermediates. The conversion typically follows a multistep indirect pathway, such as sequential hydrogenation of d-glucose to d-sorbitol in the presence of a nickel-based catalyst followed by selective oxidation of d-sorbitol using microbial enzymes. Caltech chemical engineers Rajamani Gounder and Mark E. Davis have come up with a simpler conversion method. The team reports that d-glucose can be isomerized to l-sorbose stereospecifically in a single step by using an acidic zeolite catalyst (ACS Catal. 2013, DOI: 10.1021/cs400273c). Specifically, the team found that the conversion is mediated by Ti4+ Lewis acid sites in a titanium-doped zeolite known as Ti-Beta. Zeolites are a family of porous crystalline aluminosilicates that are widely used as catalysts in oil refining and other industrial processes. On the basis of isotope labeling studies, the Caltech group proposes that the Ti-Beta-mediated isomerization proceeds through an intramolecular C5-C1 hydride shift.


This article has been sent to the following recipient:

Chemistry matters. Join us to get the news you need.