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In chemistry, a Haworth projection is a common way of writing a structural formula to represent the cyclic structure of monosaccharides with a simple three-dimensional perspective. Haworth projection approximate the shapes of the actual molecules better for furanoses —which are in reality nearly planar—than for pyranoses that exist in ...
The aldohexose that is most important in biochemistry is D-glucose, which is the main "fuel" for metabolism in many living organisms. The 2-ketohexoses psicose, fructose and tagatose occur naturally as the D-isomers, whereas sorbose occurs naturally as the L-isomer. D-Sorbose is commonly used in the commercial synthesis of ascorbic acid. [10]
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The highest numbered chiral carbon (typically to the left of the oxygen in a Haworth projection) determines whether or not the structure has a d-configuration or L-configuration. In an l -configuration furanose, the substituent on the highest numbered chiral carbon is pointed downwards out of the plane, and in a D -configuration furanose, the ...
Haworth Projection of β-D-glucopyranose. Hermann Emil Fischer won the Nobel Prize in Chemistry (1902) for his work in determining the structure of the D-aldohexoses. [1] However, the linear, free-aldehyde structures that Fischer proposed represent a very minor percentage of the forms that hexose sugars adopt in solution.
Different projections of α-D-glucopyranose. 1 = Fischer projection with C-1 at the top of the anomeric centre. C-5 is the anomeric reference atom. 2, 3 = Haworth projections.
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The stereochemical structure of a cyclic monosaccharide can be represented in a Haworth projection. In this diagram, the α-isomer for the pyranose form of a D -aldohexose has the −OH of the anomeric carbon below the plane of the carbon atoms, while the β-isomer has the −OH of the anomeric carbon above the plane.