Carbohydrates

⚗️ Carbohydrates Biochemistry

Part 1 of 7 — Monosaccharide Structure

1. Monosaccharides

polyhydroxy aldehydes (aldoses) or ketones (ketoses)

2. D/L configuration

based on highest-numbered stereocenter

3. Most natural sugars are D-sugars

Most natural sugars are D-sugars

4. Common

glucose (aldohexose), fructose (ketohexose), ribose (aldopentose)

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Key Concepts Summary

• Monosaccharides: polyhydroxy aldehydes (aldoses) or ketones (ketoses)
• D/L configuration: based on highest-numbered stereocenter
• Most natural sugars are D-sugars
• Common: glucose (aldohexose), fructose (ketohexose), ribose (aldopentose)

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Fischer & Haworth Projections

Part 2 of 7 — Fischer & Haworth Projections

1. Fischer projection

vertical = going back, horizontal = coming forward

2. Haworth projection

shows cyclic hemiacetal form

3. α anomer

-OH on anomeric carbon is axial (down in Haworth)

4. β anomer

-OH on anomeric carbon is equatorial (up in Haworth)

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Key Concepts Summary

• Fischer projection: vertical = going back, horizontal = coming forward
• Haworth projection: shows cyclic hemiacetal form
• α anomer: -OH on anomeric carbon is axial (down in Haworth)
• β anomer: -OH on anomeric carbon is equatorial (up in Haworth)

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Reactions of Monosaccharides

Part 3 of 7 — Reactions of Monosaccharides

1. Mutarotation

equilibrium between α and β anomers through open-chain form

2. Reduction

NaBH₄ → alditol (sugar alcohol)

3. Oxidation

Tollens/Benedict's → aldonic acid (reducing sugars)

4. Glycoside formation

acetal from hemiacetal + alcohol

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Key Concepts Summary

• Mutarotation: equilibrium between α and β anomers through open-chain form
• Reduction: NaBH₄ → alditol (sugar alcohol)
• Oxidation: Tollens/Benedict's → aldonic acid (reducing sugars)
• Glycoside formation: acetal from hemiacetal + alcohol

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Disaccharides & Glycosidic Bonds

Part 4 of 7 — Disaccharides & Glycosidic Bonds

1. Glycosidic bond

acetal linkage between two sugars

2. Maltose

α-1,4 (glucose-glucose)

3. Lactose

β-1,4 (galactose-glucose)

4. Sucrose

α-1,β-2 (glucose-fructose) — not a reducing sugar

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Key Concepts Summary

• Glycosidic bond: acetal linkage between two sugars
• Maltose: α-1,4 (glucose-glucose)
• Lactose: β-1,4 (galactose-glucose)
• Sucrose: α-1,β-2 (glucose-fructose) — not a reducing sugar

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Polysaccharides

Part 5 of 7 — Polysaccharides

1. Starch

amylose (linear α-1,4) and amylopectin (branched α-1,4 + α-1,6)

2. Glycogen

highly branched α-1,4 + α-1,6 (animal storage)

3. Cellulose

β-1,4 glucose (structural, not digestible)

4. Chitin

β-1,4 N-acetylglucosamine (arthropod exoskeletons)

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Key Concepts Summary

• Starch: amylose (linear α-1,4) and amylopectin (branched α-1,4 + α-1,6)
• Glycogen: highly branched α-1,4 + α-1,6 (animal storage)
• Cellulose: β-1,4 glucose (structural, not digestible)
• Chitin: β-1,4 N-acetylglucosamine (arthropod exoskeletons)

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Problem-Solving Workshop

Part 6 of 7 — Problem-Solving Workshop

1. Drawing Fischer and Haworth projections

Drawing Fischer and Haworth projections

2. Identifying anomers and epimers

Identifying anomers and epimers

3. Predicting reducing vs nonreducing sugars

Predicting reducing vs nonreducing sugars

4. Analyzing glycosidic bond types

Analyzing glycosidic bond types

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Key Concepts Summary

• Drawing Fischer and Haworth projections
• Identifying anomers and epimers
• Predicting reducing vs nonreducing sugars
• Analyzing glycosidic bond types

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Synthesis & Review

Part 7 of 7 — Synthesis & Review

1. Carbohydrate chemistry bridges organic chemistry and biochemistry

Carbohydrate chemistry bridges organic chemistry and biochemistry

2. Stereochemistry is crucial for biological function

Stereochemistry is crucial for biological function

3. Glycosidic bonds are the basis of oligosaccharides

Glycosidic bonds are the basis of oligosaccharides

4. Review

sugar structure and reactions

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Key Concepts Summary

• Carbohydrate chemistry bridges organic chemistry and biochemistry
• Stereochemistry is crucial for biological function
• Glycosidic bonds are the basis of oligosaccharides
• Review: sugar structure and reactions

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