The Oligomerization of Glucose Under Plausible Prebiotic Conditions
Autor: | Li Li, Charles L. Liotta, Kristin R. McKenna, Pamela Pollet, Zhao Li, Ramanarayanan Krishnamurthy, Merranda Schmidt, Facundo M. Fernández, Leslie T. Gelbaum |
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Rok vydání: | 2019 |
Předmět: |
chemistry.chemical_classification
Anomer Evolution Chemical Magnetic Resonance Spectroscopy Stereochemistry Acetal Origin of Life General Medicine Cellobiose Maltose Polysaccharide 01 natural sciences Mass Spectrometry chemistry.chemical_compound Glucose chemistry Space and Planetary Science 0103 physical sciences Gentiobiose Monosaccharide 010303 astronomy & astrophysics Two-dimensional nuclear magnetic resonance spectroscopy Ecology Evolution Behavior and Systematics |
Zdroj: | Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life. 49(4) |
ISSN: | 1573-0875 |
Popis: | 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. |
Databáze: | OpenAIRE |
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