Chapter 20: Problem 10
Draw Haworth and conformational structures for each of the following disaccharides: a. \(6-\mathrm{O}-\beta-D\) -glucopyranosyl- \(\beta-D\) -glucopyranose b. \(4-\mathrm{O}-\beta-D\) -galactopyranosyl- \(\alpha-D\) -glucopyranose c. \(4-\mathrm{O}-\beta-D\) -xylopyranosyl- \(\beta-L\) -arabinopyranose d. \(6-\mathrm{O}-\alpha-D\) -galactopyranosyl \(-\beta-D\) -fructofuranose
Short Answer
Step by step solution
Understanding Disaccharide Structure
Identifying Monosaccharide Units
Drawing Haworth Projections
Drawing Conformational Structures
Drawing Example a - 6-O-β-D-glucopyranosyl-β-D-glucopyranose
Drawing Example b - 4-O-β-D-galactopyranosyl-α-D-glucopyranose
Drawing Example c - 4-O-β-D-xylopyranosyl-β-L-arabinopyranose
Drawing Example d - 6-O-α-D-galactopyranosyl-β-D-fructofuranose
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Haworth Projection
- Start by understanding the sugar type (aldose or ketose) and the number of carbon atoms it has.
- Form a hexagonal or pentagonal ring based on pyranose or furanose formation.
- Position the oxygen atom in the clockwise direction (usually at the top-right corner of the ring).
- The beta form shows the hydroxyl group on the anomeric carbon (C1 for aldoses) pointing up in D-sugars.
- The alpha form has the hydroxyl group pointing down.
Conformational Structures
- Draft a zig-zag shape resembling a chair with two parallel lines depicting the main carbon chain.
- Identify axial and equatorial positions for substituents, crucial for stereochemistry understanding.
Glycosidic Bonds
- Formation can occur in alpha or beta configurations, affecting the resulting structure and linkage direction.
- Numbering the carbon atoms is crucial for identifying which carbons participate in the bond, usually denoted like 1→4 or 1→6 linkages.
Pyranose and Furanose Forms
- Pyranose forms result from cyclicization at the C1 for aldoses or C2 for ketoses and involves the creation of a hemiacetal or hemiketal linkage.
- Furanose forms usually involve the carbonyl group reacting with an oxygen from a hydroxyl group further away, such as C1 and C5 in glucose labeling to form a five-membered ring.