Textbook Question
Indicate whether the following statements apply to type 1 or type 2 diabetes:
(c) can be managed with diet and exercise
Ch.6 Carbohydrates Life's Sweet Molecules
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696
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Table of contents
- Ch.4 Introduction to Organic Compounds75
- Ch.5 Chemical Reactions19
- Ch.6 Carbohydrates Life's Sweet Molecules62
- Ch.7 States of Matter and Their Attractive Forces8
- Ch.8 Solution Chemistry Sugar and Water Do Mix4
- Ch.10 Proteins Workers of the Cell89
- Ch.11 Nucleic Acids Big Molecules with a Big Role69
- Ch.12 Food as Fuel An Overview of Metabolism65
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
Chapter 3, Problem 25
Draw the ⍺ and β anomer of D-talose in pyranose ring form:
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Understand that d-talose is a monosaccharide (aldose) with the molecular formula C6H12O6. It has four chiral centers, and its structure determines the arrangement of hydroxyl (-OH) groups on the carbon atoms.
Recognize that the pyranose ring form is a six-membered ring structure formed when the hydroxyl group on the C5 carbon reacts with the aldehyde group on the C1 carbon, creating a hemiacetal linkage.
To draw the α-anomer, place the hydroxyl group on the C1 carbon (anomeric carbon) pointing down (axial position) in the Haworth projection. Ensure the other hydroxyl groups on C2, C3, and C4 are positioned according to the stereochemistry of d-talose.
To draw the ß-anomer, place the hydroxyl group on the C1 carbon (anomeric carbon) pointing up (equatorial position) in the Haworth projection. Again, ensure the other hydroxyl groups on C2, C3, and C4 are positioned according to the stereochemistry of d-talose.
Verify the stereochemistry of d-talose in both α and ß forms by checking the orientation of the hydroxyl groups on each chiral center (C2, C3, C4) and ensure the pyranose ring is correctly closed with the oxygen atom forming the ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Anomers
Anomers are a type of stereoisomer that differ in configuration at the anomeric carbon, which is the carbon atom that becomes a new chiral center when a sugar cyclizes. In the case of d-talose, the α and ß anomers refer to the orientation of the hydroxyl group (-OH) attached to the anomeric carbon. In the α-anomer, the -OH group is positioned on the opposite side of the ring from the CH2OH group, while in the ß-anomer, it is on the same side.
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Cyclic Structures of Monosaccharides Concept 1
Pyranose Ring Structure
The pyranose ring structure is a six-membered cyclic form of sugars, which includes five carbon atoms and one oxygen atom. This structure is formed when the carbonyl group of an aldose reacts with a hydroxyl group on the same molecule, leading to the formation of a hemiacetal. Understanding the pyranose form is essential for visualizing the anomeric carbon and the resulting stereochemistry of the sugar.
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D-Configuration
D-configuration refers to the specific orientation of the hydroxyl groups in a sugar molecule, particularly at the penultimate carbon (the second-to-last carbon). In d-talose, the 'D' indicates that the hydroxyl group on this carbon is on the right side in a Fischer projection. This configuration is crucial for distinguishing between different sugars and understanding their biochemical roles and properties.
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Related Practice
Textbook Question
Pentoses also exist in a ring form, but they most commonly occur as furanose rings. D-Ribose exists in its furanose ring form in the nucleic acid RNA. Using the structure of D-ribose from Table 6.1, draw the furanose form of β-D-ribose.
Textbook Question
Identify the following carbohydrates as the ⍺ or β anomer:
(a)
Textbook Question
Indicate whether the following statements apply to type 1 or type 2 diabetes:
(a) most cases begin in youth
Textbook Question
The sugar alcohol erythritol is often included in low-calorie sweeteners. It is 70% as sweet as table sugar. Erythritol is the reduced form of the aldotetrose erythrose. Draw erythritol.
Textbook Question
The sugar alcohol ribitol is a component of the vitamin riboflavin and the energy transfer molecule FAD. Ribitol is formed when the monosaccharide ribose undergoes reduction at carbon 1. Draw the structure of ribitol.