Results
Title

The Oligomerization of Glucose Under Plausible Prebiotic Conditions.

Authors

Li, Zhao; Li, Li; McKenna, Kristin R.; Schmidt, Merranda; Pollet, Pamela; Gelbaum, Leslie; Fernández, Facundo M.; Krishnamurthy, Ramanarayanan; Liotta, Charles L.

Abstract

The prebiotic origin of polysaccharides, the largest class of biopolymers by mass in extant biology, has seldom been investigated experimentally. Herein, we report on the acid-catalyzed condensation of aqueous solutions of glucose, a model monosaccharide, under plausible prebiotic conditions employing a wet-dry (night-day) protocol with 0.01 M HCl at 50 °C. This protocol leads to the formation of oligosaccharides containing up to eight monomeric units identified by high resolution mass spectrometry. The regio- and stereochemistry of the oligomeric acetal linkages, as well as the quantitative analysis of glucose conversion, are elucidated by combining 1H, 13C and 2D NMR spectroscopy. Ten out of eleven possible acetal linkages, including α- and β- anomers, have been identified with the α- and β- 1,6-acetals being the dominant linkages observed. In addition, the acid-catalyzed oligomerization of several glucose disaccharides such as cellobiose, maltose, and gentiobiose are presented along with an accompanying comparison with the corresponding oligomerization of glucose.

Subjects

GLUCOSE analysis; GLUCOSE; OLIGOMERIZATION; MONOSACCHARIDES; DISACCHARIDES; NUCLEAR magnetic resonance spectroscopy

Publication

Origins of Life & Evolution of the Biosphere, 2019, Vol 49, Issue 4, p225

ISSN

0169-6149

Publication type

Academic Journal

DOI

10.1007/s11084-019-09588-3