Related Experiment Video
Updated: Jun 8, 2026
14:18
A Strategy for Sensitive, Large Scale Quantitative Metabolomics
Published on: May 27, 2014
4-Deoxy-4-fluoro-β-D-glucopyranose.
Wenhui Zhang1, Allen G Oliver, Anthony S Serianni
1Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556-5670, USA.
Summary
4-Deoxy-4-fluoro-β-D-glucopyranose exhibits a distorted chair conformation in its crystal structure. This fluorinated sugar shares similar hydrogen bonding and crystal packing with β-D-glucopyranose.
Area of Science:
- Carbohydrate chemistry
- Crystallography
- Structural analysis
Background:
- Understanding the structural nuances of monosaccharides is crucial for various biochemical and pharmaceutical applications.
- Fluorine substitution in carbohydrates can significantly alter their physical and biological properties.
- Comparative structural analysis provides insights into structure-activity relationships.
Purpose of the Study:
- To elucidate the crystal structure of 4-Deoxy-4-fluoro-β-D-glucopyranose.
- To compare its conformation and intermolecular interactions with β-D-glucopyranose.
- To investigate the impact of fluorine substitution on carbohydrate crystal packing.
Main Methods:
- Single-crystal X-ray diffraction analysis.
- Cremer-Pople conformational analysis.
- Comparative analysis of hydrogen bonding and crystal packing.
Main Results:
- 4-Deoxy-4-fluoro-β-D-glucopyranose crystallizes in a distorted (4)C(1) chair conformation, differing from β-D-glucopyranose.
- The fluorinated sugar's conformation is skewed towards a B(C3,O5) boat conformer.
- Identical patterns of intermolecular hydrogen bonding and crystal packing were observed for both compounds.
Conclusions:
- Fluorine substitution at the 4-position of β-D-glucopyranose leads to a subtle but distinct change in the ring conformation.
- The exocyclic hydroxymethyl group conformation remains conserved between the two sugars.
- Crystal packing and hydrogen bonding networks are remarkably similar, suggesting robust intermolecular interactions in these monosaccharides.
More Related Videos
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
09:27Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
Related Concept Videos
01:21Glycolysis: Preparatory Phase
In cellular metabolism (the complete breakdown of glucose to extract energy), glycolysis is the first step. Glycolysis takes place in the cytoplasm of both prokaryotic and eukaryotic cells. Glucose enters heterotrophic cells in two ways. One method is through secondary active transport, where the transport takes place against the glucose concentration gradient. The other mechanism uses a group of integral proteins called GLUT proteins, also known as glucose transporter proteins. These...
01:26Biosynthesis of Polysaccharides
Polysaccharides such as glycogen and starch are synthesized from nucleoside diphosphate sugars, primarily uridine diphosphate glucose (UDPG) and adenosine diphosphate glucose (ADPG). These activated glucose donors act as key intermediates in carbohydrate metabolism and biosynthesis. UDPG primarily involves glycogen synthesis in animals and many bacteria, while ADPG plays a fundamental role in starch synthesis in plants and certain bacteria.UDPG is formed when glucose-1-phosphate reacts with...
01:20Energy-requiring Steps of Glycolysis
Glucose is the source of nearly all energy used by organisms. The first step of converting glucose into usable energy is called glycolysis. Glycolysis occurs in the cytosol of the cell over two phases: an energy-requiring phase and an energy-releasing phase. Over the first three steps, glucose is converted into different forms and attached to two phosphate groups donated by two ATP molecules, resulting in an unstable sugar. In the next two stages, the unstable sugar splits into two sugar...
01:24Other Glycolytic Pathways
The pentose phosphate pathway (PPP) operates in parallel with glycolysis, facilitating the metabolism of both pentoses and glucose. This pathway consists of two distinct phases: the oxidative and non-oxidative phases. While it does not directly generate ATP, the intermediates formed during the process can integrate into glycolysis, contributing to cellular energy metabolism when required.Oxidative Phase: NADPH ProductionThe oxidative phase of the pentose phosphate pathway is primarily...
01:24Oligosaccharide Assembly
Protein glycosylation starts in the ER lumen and continues in the Golgi apparatus. Glycosyltransferases catalyze the addition of sugar molecules or glycosylation of proteins. Usually, these enzymes add sugars to the hydroxyl groups of selected serine or threonine residues to form O-linked glycans or the amino groups of asparagine residues to form N-linked glycans. Different positions on the same polypeptide chain can contain differently linked glycans.
Multiple sugar molecules that may or may...
Multiple sugar molecules that may or may...
02:18Fischer Projections
Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...