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a) L-fucose is also known as 6-deoxy-L-galactose. Note that D-galactose is a C-4 epimer of D-glucose. Draw the Fisher projections for D-glucose, D-galactose and L-fucose. (Hints: D- and L-isomers are enantiomers. 6-deoxy means that the hydroxyl group at C-6 is removed leaving just the methyl group). L-fucose D-glucose: D-galactose: (6-deoxy-L-galactose): b) L-fucose can cyclize into a pyranose and form two anomers. Draw the Haworth diagrams for the a- and ß- anomers of L-fucose. a-L-fucopyranose: B-L-fucopyranose:

a) L-fucose is also known as 6-deoxy-L-galactose. Note that D-galactose is a C-4 epimer of D-glucose. Draw the Fisher projections for D-glucose, D-galactose and L-fucose. (Hints: D- and L-isomers are enantiomers. 6-deoxy means that the hydroxyl group at C-6 is removed leaving just the methyl group). L-fucose D-glucose: D-galactose: (6-deoxy-L-galactose): b) L-fucose can cyclize into a pyranose and form two anomers. Draw the Haworth diagrams for the a- and ß- anomers of L-fucose. a-L-fucopyranose: B-L-fucopyranose:

Biochemistry
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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### Section VI: Monosaccharide Configuration in Glycoproteins **Overview:** Most biologically relevant sugars possess the D-configuration; however, L-fucose is a common monosaccharide in glycoproteins. Glycosylated antibodies (IgGs) show higher levels of fucose in those with active tuberculosis (TB) compared to latent TB patients. Latent TB is characterized by controlled bacterial proliferation, resulting in an asymptomatic and non-infectious state. These individuals test positive for TB via tuberculin or blood tests. **a) Structural Projections:** L-fucose, or 6-deoxy-L-galactose, is structurally related to D-glucose and D-galactose. D-galactose is a C-4 epimer of D-glucose. The task is to draw Fisher projections for the mentioned sugars. Fisher projections are a method of depicting stereochemistry in sugars, indicating the orientation of hydroxyl groups. - **D-glucose** - Standard configuration with hydroxyl groups oriented in a specific pattern. - **D-galactose** - Similar to glucose but as a C-4 epimer, meaning there’s a specific configuration at the fourth carbon. - **L-fucose (6-deoxy-L-galactose)** - Differs by lacking the hydroxyl group on the sixth carbon, substituted by a methyl group. **b) Cyclization and Anomer Formation:** L-fucose can cyclize into a pyranose ring, forming two anomers: α-L-fucopyranose and β-L-fucopyranose. These anomers differ in the orientation of the substituent at the anomeric carbon. - **α-L-fucopyranose** - The anomeric hydroxyl group is oriented in one direction relative to the pyranose ring. - **β-L-fucopyranose** - The anomeric hydroxyl group is oriented in the opposite direction compared to the α-anomer. **Visual Aids:** Fisher projections and Haworth diagrams provide visual understanding of these structural differences and are crucial for illustrating the stereochemistry of monosaccharides.
Transcribed Image Text:### Section VI: Monosaccharide Configuration in Glycoproteins **Overview:** Most biologically relevant sugars possess the D-configuration; however, L-fucose is a common monosaccharide in glycoproteins. Glycosylated antibodies (IgGs) show higher levels of fucose in those with active tuberculosis (TB) compared to latent TB patients. Latent TB is characterized by controlled bacterial proliferation, resulting in an asymptomatic and non-infectious state. These individuals test positive for TB via tuberculin or blood tests. **a) Structural Projections:** L-fucose, or 6-deoxy-L-galactose, is structurally related to D-glucose and D-galactose. D-galactose is a C-4 epimer of D-glucose. The task is to draw Fisher projections for the mentioned sugars. Fisher projections are a method of depicting stereochemistry in sugars, indicating the orientation of hydroxyl groups. - **D-glucose** - Standard configuration with hydroxyl groups oriented in a specific pattern. - **D-galactose** - Similar to glucose but as a C-4 epimer, meaning there’s a specific configuration at the fourth carbon. - **L-fucose (6-deoxy-L-galactose)** - Differs by lacking the hydroxyl group on the sixth carbon, substituted by a methyl group. **b) Cyclization and Anomer Formation:** L-fucose can cyclize into a pyranose ring, forming two anomers: α-L-fucopyranose and β-L-fucopyranose. These anomers differ in the orientation of the substituent at the anomeric carbon. - **α-L-fucopyranose** - The anomeric hydroxyl group is oriented in one direction relative to the pyranose ring. - **β-L-fucopyranose** - The anomeric hydroxyl group is oriented in the opposite direction compared to the α-anomer. **Visual Aids:** Fisher projections and Haworth diagrams provide visual understanding of these structural differences and are crucial for illustrating the stereochemistry of monosaccharides.
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