Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic...

54
Carbohydrates

TAGS:

Transcript of Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic...

Page 1: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Carbohydrates

Page 2: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Structure of Carbohydrates

O

HO

CH2OH

OH

OH

O

CH2OH

OH

OH

OH

O

O

HO

CH2OH

OH

OH

O—HO

H—O

CH2OH

OH

OH

OH

H2O

Sugars OligosaccharidesPolysaccharides

Page 3: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Properties of Carbohydrates

• Most abundant class of organic molecules

• Source: Photosynthesis• Classification

– Monosaccharides• Stereoisomers• Aldehydes (Aldose) or Ketones (Ketose)• Number of Carbons (ie 3=triose; 6=hexose)• Combined: Aldotriose/Ketotetrose

– Polymers• Oligosaccharides (2- ~20 sugars)• Polysaccharides (> ~20 sugars)

Page 4: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Biological Roles of Carbohydrates

• Energy source• Energy storage• Cell walls• Recognition events

– Between proteins (targeting)– Between cells

• Signalling• Components of other biological

molecules– Antibiotics– Enzyme cofactors– Nucleic Acids

Page 5: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Monosaccharides(Sugars)

Page 6: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Classes of Monosaccharides

C

C

CH2OH

H O

H OH

CH2OH

C

CH2OH

O

D-Glyceraldehyde Dihydroxyacetone

Aldoses(Aldehydes)

Ketoses(Ketones)

Page 7: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Chirality

C

C

CH2OH

H O

H OH

D-Glyceraldehyde

C

C

CH2OH

H O

OH H

L-Glyceraldehyde

D- versus L- determined by chirality of highest number carbon (from aldehyde or ketone)

Page 8: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Figure 8-1

Aldoses

Page 9: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Figure 8-1

Aldoses

Page 10: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Figure 8-2

Ketoses

Page 11: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Figure 8-2

Ketoses

Page 12: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Epimers(stereoisomers differing by configuration

of only one of several chiral centers)

C

C

H O

H

C

C

H O

H OH

CH2OH

CHO H

CH OH

CHO H

C

C

H O

H OH

CH2OH

CHO H

CH OH

CH OH

OH

CH2OH

CHO H

CHO H

CH OH

D-Galactose (gal)D-Glucose (glc) D-Mannose (man)

Page 13: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Epimers(stereoisomers differing by configuration

of only one of several chiral centers)

C

C

H O

H

C

C

H O

H OH

CH2OH

CHO H

CH OH

CHO H

C

C

H O

H OH

CH2OH

CHO H

CH OH

CH OH

OH

CH2OH

CHO H

CHO H

CH OH

D-Galactose (gal)D-Glucose (glc) D-Mannose (man)

Page 14: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Enantiomers(mirror images)

C

C

H O

HO H

CH2OH

CH OH

CHO H

CHO H

C

C

H O

H OH

CH2OH

CHO H

CH OH

CH OH

L-GlucoseD-Glucose

Page 15: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Mutarotation

Creation of new chiral center

Page 16: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Formation of Hemiacetal

O

CR H

+

..

O

C

O

HR

R1

H

..+

Chiral

H

H R1

O

H

Page 17: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Formation of Hemketal

O

CR R2

O

C

O

R2R

R1

H

Chiral

..

..

+

+R1H

O

H

H

Page 18: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Anomeric Carbon Atom

MutarotationReversible

Creation of new asymmetric center

Page 19: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Cyclization of D-Glucose

Page 20: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Anomers

• Anomeric carbon atom– Most oxidized carbon atom– Shares electrons with 2 oxygen atoms

-configuration has -OH on opposite side of ring from CH2OH group at chiral center that designates D- or L-

Page 21: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Cyclization of D-Fructose(biologically relevant forms)

CH2OH

C

O

H OH

CH2OH

CHO H

CH OH

CHOCH2 CH2OH

OH

OH

OH

HOCH2 OH

CH2OH

OH

OH

O O

D-Fructose -D-Fructose-D-Fructose

Page 22: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Nomenclature

O

pyran

O

f uran

Pyranoses Furanoses

Page 23: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Examples of Nomenclature

-D-glucopyranose

-D-fructofuranoseConfiguration of anomeric carbon

Configuration of sugar

Sugarprefix

RingType*not required

Anomeric carbon modification:ose: reducingoside: non-reducing

Page 24: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Cyclization of D-Fructose(biologically relevant forms)

CH2OH

C

O

H OH

CH2OH

CHO H

CH OH

CHOCH2 CH2OH

OH

OH

OH

HOCH2 OH

CH2OH

OH

OH

O O

D-Fructose -D-Fructose-D-Fructose

Page 25: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Figure 8-5

Chair Conformations of -D-glucopyranose

Chair and Boat Forms

Equitorial and Axial Substituents

Steric Crowding: equitorial more stable

Equatorial Axial

Page 26: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Derivatives of Monosaccharides

Page 27: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Phosphate Esters

OO OH

OH

OH

HO

OH

CH2OPO32–

OH

OH

CH2OPO32–

-D-Fructose-1,6-bisphosphate (Fru-1,6-bisP)

-D-Glucose-6-P (Glc-6-P)

=O3POCH2

CH2OH

C O

CH2OPO32–

C

C OHH

OH

CH2OPO32–

C

C OHH

OH

C OHH

CH2OPO32–

D-Erythrose4-phosphate (E4P)

D-Glyceraldehyde 3-phosphate (G3P)

Dihydroxyacetone phosphate (DHAP)

Page 28: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Deoxy Sugars

O

OH

OH

O

OH

OH

2-Deoxyribose (dRib)

Deoxyribose 5-phosphate (dRib-5-P)[Deoxy--D-ribof uranose 5-phosphate]

HOCH22–O3POCH2

Note: 5-membered ring form is used in biological systems

Page 29: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Amino Sugars(e.g. GlcNAc-6-P)

O OH

NH

OH

HO

CH2OP

C

H3C O

N-Acetyl-D-glucosamine 6-phosphate

Page 30: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Sugar Alcohols

C

CH OH

CH2OH

CH OH

CH OH

CH2OH

CH OH

CH2OH

CH OH

CH OH

OH

D-Ribose Ribitol

CH2OH

CH OH

CH2OH

CHO H

CH OH

CH OH

C

C

H O

H OH

CH2OH

CHO H

CH OH

CH OH

D-Glucose Sorbitol

Page 31: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Glycosides

Page 32: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Structure of Glycosides

PolymerizationMonomers(Sugars)

Polymers(Disaccharides)

(Oligosaccharides)(Polysaccharides)

NOTE: linear and branched polymers

Page 33: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Glycosidic Linkages (glycoside)

O

CH2OH

OCH3

OH

OH

HO

Acetal

Stable: no mutarotation

Non-reducing sugar (no free anomeric C atom)

Page 34: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Nomenclature

O

CH2OH

OCH3

OH

OH

HO

O

CH2OH

OH

OH

OH

CH3O

OHOCH2 OCH3

CH2OH

OH

HO

Optional

[Non-reducing][Reducing][Non-reducing]

Methyl--D-Fructofuranoside

4-O-Methyl--D- Glucopyranose

O-Methyl--D-Glucopyranoside

Page 35: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Reducing test

• Free Aldehydes are reductants

• If free to mutarotate sugar is a reductant– Must have only –OH

at anomeric carbon

Cupric oxidebrick-red

precipitate

Cu2O

Page 36: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Disaccharides

Page 37: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Sucrose (non-reducing)

O

CH2OH

OH

OH

HOO

OHOCH2

CH2OH

OH

OH

OHOCH2 OH

CH2OH

OH

OH

-D-f ructose

-D-glucopyranosyl-(l __> 2)--D-f ructofuranoside

OR: Glc(α1 β2)Fru

Page 38: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Sucrose

O

CH2OH

OH

OH

HOO

OHOCH2

CH2OH

OH

OH

OHOCH2 OH

CH2OH

OH

OH

-D-f ructose

-D-glucopyranosyl-(l __> 2)--D-f ructofuranoside

OR: Glc(α1 β2)Fru

Page 39: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

-Maltose

O

CH2OH

OH

OH

HOO

O

CH2OH

OH

OH

OH

-D-glucopyranosyl-(l __> 4)--D-glucopyranose

Glc(α14)Glc

Page 40: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

-Lactose

Gal(β14)Glc

Page 41: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Nomenclature

1. Recognize individual monosaccharides2. Drop the –se and add root for rings

– 6 member: pyran– 5 member: furan

3. Attach:– ose: can mutarotate– oside: canNOT mutarotate– osyl: not terminal residue

4. Indicate carbon to carbon number linkage (##)

5. Label each residue with D or L and α or β

Page 42: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Oligosaccharides

• Generally complex– Heteropolymers– Branched

• Various Cellular Functions– Receptors– Antigens– Signal transduction– Trafficking

Page 43: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

O-linked Oligosaccharides(serine/threonine)

Page 44: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

N-linked Oligosaccharides(asparagine)

Page 45: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Sugar groups on glycoproteins frequently function in recognition

Page 46: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Polysaccharides

• Simpler structures– Homopolymers– Less branching

• Limited Cellular Functions– Structural/Protective– Energy Storage

Page 47: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Linear Polysaccharides

reducing end (RE)non-reducing end (NRE)

glycosidic linkages

Page 48: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Branched Polysaccharides

RE

NRE

glycosidic linkages

Page 49: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Functions of Polysaccharides

• Structural - e.g. plant cell walls, cement between cells (animals): • -linkages stable to enzymatic cleavage

• Storage - e.g. glycogen as energy reserves:• -linkages are readily cleaved

• Potential osmotic problem

• Accessibility for energy production -linkages

• Branching

Page 50: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Cellulose(plant cell walls)

O

CH2OH

O OH

OH

O

O

CH2OH

OH

OH

O

-(1___>4)

Page 51: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Chitin(1—>4)-linked homopolymer of

N-acetylglucosamine

Exoskeletin of invertebrates (e.g. crustacians, insects, and spiders)

Cell wall (most fungi and some algae)

Page 52: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Glycogen(storage)

Linear: α14Branches: α16

O

CH2OH

HO O

OH

OH

O

O

CH2OH

OH

OH

O

CH2OH

HO O

OH

OH

O

CH2OH

OH

OH

O

CH2

O

OH

OH

O

CH2OH

OH

OH

OHO

Page 53: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Starch(plants)

linear

branched (similar to glycogen, but fewer branches)

Page 54: Carbohydrates. Structure of Carbohydrates Properties of Carbohydrates Most abundant class of organic molecules Source: Photosynthesis Classification.

Photosynthesis IB topic 3.8 (page 83). What is photosynthesis? Photosynthesis is the production of organic compounds (carbohydrates, lipids, and proteins)

Photosynthesis IB topic 3.8 (page 83). What is photosynthesis? Photosynthesis is the production of organic compounds (carbohydrates, lipids, and proteins)

Photosynthesis Chapter 4. Photosynthesis Photosynthesis- the production of carbohydrates from carbon dioxide and water in the presence of chlorophyll.

Photosynthesis Chapter 4. Photosynthesis Photosynthesis- the production of carbohydrates from carbon dioxide and water in the presence of chlorophyll.

Carbohydrates. Introduction: Carbohydrates are the most abundant organic compounds in the plant world They are storehouses of chemical energy (glucose,

Carbohydrates. Introduction: Carbohydrates are the most abundant organic compounds in the plant world They are storehouses of chemical energy (glucose,

Carbohydrates+(sugars)+are+polyhydroxy+ aldehydes+or+ketones.+depa.fquim.unam.mx/amyd/archivero/CARBOHIDRATOS_24461.pdf · • Carbohydrates+(sugars)+are+abundant+in nature: – They+arehigh+en

Carbohydrates+(sugars)+are+polyhydroxy+ aldehydes+or+ketones.+depa.fquim.unam.mx/amyd/archivero/CARBOHIDRATOS_24461.pdf · • Carbohydrates+(sugars)+are+abundant+in nature: – They+arehigh+en

CHAPTER 15 Carbohydrates. Where in the world do we find carbohydrates? Most abundant organic compound in nature Photosynthesis: plants make glucose using.

CHAPTER 15 Carbohydrates. Where in the world do we find carbohydrates? Most abundant organic compound in nature Photosynthesis: plants make glucose using.

Carbohydrates B.3. Introduction most abundant class of biological molecules range from simple sugars (glucose) to complex carbohydrates (starch)

Carbohydrates B.3. Introduction most abundant class of biological molecules range from simple sugars (glucose) to complex carbohydrates (starch)

Chapter 7 Carbohydrates and Glycobiology. Carbohydrates The most abundant biomolecules on Earth Many carbohydrates: (CH 2 O) n Polyhydroxy aldehydes.

Chapter 7 Carbohydrates and Glycobiology. Carbohydrates The most abundant biomolecules on Earth Many carbohydrates: (CH 2 O) n Polyhydroxy aldehydes.

Carbohydrates Chapter 8. Carbohydrates Of the macromolecules that we will cover in this class, those involving carbohydrates are the most abundant in.

Carbohydrates Chapter 8. Carbohydrates Of the macromolecules that we will cover in this class, those involving carbohydrates are the most abundant in.

UNIT 4. CARBOHYDRATES - RUA: Principalrua.ua.es/dspace/bitstream/10045/38480/2/U4-Degree_ARA_correction_EN.pdf · 4.1 INTRODUCTION : • Carbohydrates are the single most abundant

UNIT 4. CARBOHYDRATES - RUA: Principalrua.ua.es/dspace/bitstream/10045/38480/2/U4-Degree_ARA_correction_EN.pdf · 4.1 INTRODUCTION : • Carbohydrates are the single most abundant

1 Carbohydrates Sugars or Saccharides One of the most abundant compounds of living cells In living cells (plants) -> carbohydrates are made by photosynthesis.

1 Carbohydrates Sugars or Saccharides One of the most abundant compounds of living cells In living cells (plants) -> carbohydrates are made by photosynthesis.

Introduction to Carbohydrates. importance of carbohydrates Carbohydrates are initially synthesized in plants by photosynthesis. important for Carbohydrates.

Introduction to Carbohydrates. importance of carbohydrates Carbohydrates are initially synthesized in plants by photosynthesis. important for Carbohydrates.

Carbohydrates are the most abundant macromolecules of life are made up entirely of C, H, O Functions of Carbohydrates are: Plant Structure cellulose gives.

Carbohydrates are the most abundant macromolecules of life are made up entirely of C, H, O Functions of Carbohydrates are: Plant Structure cellulose gives.

Carbohydrates. Most abundant class of biological molecules on Earth Originally produced through CO 2 fixation during photosynthesis.

Carbohydrates. Most abundant class of biological molecules on Earth Originally produced through CO 2 fixation during photosynthesis.

Basic Plant Biochemistry Chapter 7 Carbohydrates Of the macromolecules that we will cover in this class, those involving carbohydrates are the most abundant.

Basic Plant Biochemistry Chapter 7 Carbohydrates Of the macromolecules that we will cover in this class, those involving carbohydrates are the most abundant.

CARBOHYDRATES. Carbohydrates - the most abundant class of biological molecules on Earth Empirical formula - (CH 2 O) n, where n ≥ 3 -consist of three.

CARBOHYDRATES. Carbohydrates - the most abundant class of biological molecules on Earth Empirical formula - (CH 2 O) n, where n ≥ 3 -consist of three.

Unit 1 – CH 3 Photosynthesis · 2018-09-10 · Photosynthesis -Photosynthesis combines carbon dioxide and water in the presence of sunlight, and chlorophyll to produce carbohydrates

Unit 1 – CH 3 Photosynthesis · 2018-09-10 · Photosynthesis -Photosynthesis combines carbon dioxide and water in the presence of sunlight, and chlorophyll to produce carbohydrates

Chapter 8 (part 1) Carbohydrates. Most abundant class of biological molecules on Earth Originally produced through CO 2 fixation during photosynthesis.

Chapter 8 (part 1) Carbohydrates. Most abundant class of biological molecules on Earth Originally produced through CO 2 fixation during photosynthesis.

Chapter 6 Carbohydrates. Vocabulary Carbohydrates Photosynthesis Chlorophyll Sugar Simple Carbohydrates Monosaccharide Disaccharide Starch Polysaccharide.

Chapter 6 Carbohydrates. Vocabulary Carbohydrates Photosynthesis Chlorophyll Sugar Simple Carbohydrates Monosaccharide Disaccharide Starch Polysaccharide.

Photosynthesis - marwaricollege.ac.in · “Photosynthesis is a photo-biochemical process (anabolic & endergonic) in which organic compound (carbohydrates) are synthesized from the

Photosynthesis - marwaricollege.ac.in · “Photosynthesis is a photo-biochemical process (anabolic & endergonic) in which organic compound (carbohydrates) are synthesized from the

Photsynthesis/Respiration. Radiant energy carbohydrates Respiration How energy flows through the ecosystem Photosynthesis Heterotrophs Autotrophs heat.

Photsynthesis/Respiration. Radiant energy carbohydrates Respiration How energy flows through the ecosystem Photosynthesis Heterotrophs Autotrophs heat.