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Home , Aldose, Anomer, Carbohydrate, Glycosidic bond, Hexose, Ketose

CARBOHYDRATES: STRUCTURE AND

 Color index: . Very important . Extra Information.

“ STOP SAYING I WISH, START SAYING I WILL” 435 Team *هذا العمل ال يغني عن المصدر المذاكرة الرئيسي OBJECTIVES: • • • . glycosaminoglycans. The of and storing The physiological The structure of ofcarbohydrates structure and function of main role ofcarbohydrates inproviding significance. . 435 Biochemistry Biochemistry Team extra information that might help you

1-synovial fluid: - It is a viscous, non-Newtonian fluid found in the cavities of synovial joints. - the principal role of synovial fluid is to reduce friction between the articular cartilage of synovial joints during movement O 2- = terminal (RCHO) R H

3- = carbonyl group within (inside) the compound (RCOR’)

435 Biochemistry Team the most abundant organic molecules in nature

(CH2O)n Formula * of *

Function

1-provides important part of energy Diseases caused by disorders of in diet . 2-Acts as the storage form of energy in the body 3-structural component of membrane. 1-Diabetesmellitus. 2-. 3- storage disease. 4-Lactoseintolerance.

435 Biochemistry Team Classification of carbohydrates

simple Two monosaccharides 3-10 sugar units units more than 10 sugar units

Joining of 2 monosaccharides No. of carbon Type of carbonyl by O-: they contain group they contain - (α-1, 4)= + glucose - (α-1,2)= glucose + - (β-1,4)= glucose+ Homopolysaccharides Heteropolysaccharides Ketone or aldehyde Homo= same type of

Hetero= different types of sugars branched unBranched -Example: - Contains: - Contains: Examples: aldehyde group glycosaminoglycans ketone group. Glycogen and (GAGs) Example: (α-glycosidic Type of ) No. of Ccarbonyl Aldose Ketose (β- glycosidicpolyme r

Pentose Glucose Fructose 435 Biochemistry Team 435 Biochemistry Team Monosaccharides

. Monosaccharaides is basic unit of carbohydrate ( simple sugar ) Classification of Monosaccharaides according to

No. of carbon Type of carbonyl atoms they contain group they contain

No. of Generic carbon example name atoms

3 Glyceraldehyde Functional sugar group: . Aldehyde group – ( carbonyl group is terminal 4 (at the end of chain ) ) . Keto group – ( carbonyl group is within the chain ) 5 Ribose Type of carbonyl 6 Glucose No. of C Aldose Ketose

7 Sedoheptolose Triose Glyceraldehyde Dihydroxyacetone

Pentose Ribose Ribulose 9 Neuraminic Hexose 435 BiochemistryGlucose Team Fructose DISACCHARIDES

Joining of 2 's by o-glycosidic bond Examples: C4 of the second glucose 1- Maltose (α-1, 4)= glucose + glucose

OH toward down C1 of the first glucose

2- Sucrose (α-1,2)=glucose + fructose 3- Lactose (β-1,4)=glucose + galactose

Note: α= OH down Β= OH up

435 Biochemistry Team polysaccharides

Homopolysaccharides Heteropolysaccharides Homo= same type of sugars Hetero= different types of sugars -Example: glycosaminoglycans Branched unBranched (GAGs) -One chain but it has a -Single chain branch on it Example: Examples: Glycogen and starch Cellulose (α-glycosidic polymer) (β-glycosidicpolymer)

435 Biochemistry Team #:

Compounds with the same but with a different structural formula.

Note: Galactose, Glucose, , and Fructose are all isomers of each other *The chemical formula is: C6H12O6 #Types:

Same  formula •

Aldo-Keto Different  •

Same  formula •

Epimers Different  configuration around a *single* carbon .•

Same  molecular formula • D- and L- Different position of OH group on the *asymmetric carbon* farthest from carbonyl group.• forms

Same  molecular formula • α- and β- Different  position of OH around anomeric carbon•

435 Biochemistry Team #Aldo-Keto Isomers (Functional group isomerism): What are they? two compounds with the same molecular formula, but different functional group Example: Glucose (Aldose) and Fructose (Ketose) Recall aldose is a monosaccharide (a simple sugar) that contains only one aldehyde (−CH=O) group per molecule. ketose is a monosaccharide containing one ketone group per molecule

#:

What are they? Compounds that have the same chemical formula but they differ only in the configuration around a single carbon atom Examples: -Glucose and galactose (epimers at C4) -Glucose and Mannose (epimers at C2) * Galactose and mannose are not epimers

NOTE: when 2 compounds differ in the configuration around * Galactose and mannose are not epimers more than one carbon they don’t considered as epimers . (D- and L-Forms)

What are they? Structures that are mirror images of each other and are designated as D- and L- sugars based on the position of –OH group on the asymmetric carbon farthest from the carbonyl carbon

Majority of sugars in humans are D-sugars 

NOTES: D and L-forms have to be optically active. - asymmetric carbon (chiral carbon) is: a carbon atom attached to 4 different groups.

- The basic requirement of structural formula to be optically active is to has at least one asymmetric carbon atom

- when the OH group is on the right of the molecule D-molecule. - when the OH group is on the left of the molecule,  L-molecule.

435 Biochemistry Team α- and β- Forms (Anomers)

- Cyclization of Monosaccharides with 5 or more carbon are predominantly found in the ring form. - The aldehyde or ketone group reacts with the –OH grp on the same sugar - Cyclization creates an *anomeric carbon* (former carbonyl carbon) generating the α and β configurations. NOTE: - in the case of Glucose, the carbonyl carbon reacts with C5 and makes a ring. - The hydroxyl group can go up or down so that is the formation of isomers (anomers) : -In solution, the cyclic α and β anomers of sugars are in equilibrium with each other, and can be interconverted spontaneously.

Definetions that might help you: *Anomeric carbon: The carbon at which anomers rotate. *: stereoisomers of a sugar which differ only in how they are configured around anomeric carbon. *Stereoisomers : are isomeric molecules that have the same molecular formula and sequence of bonded atoms but differ in the three-dimensional orientations of their atoms in space.

435 Biochemistry Team A REDUCING SUGAR : is any sugar that is capable of acting as a reducing agent because it has a free aldehyde group or a free ketone group … in other words when the O on the anomeric C of a sugar is not attached to any other structure (Free), that sugar can act as a reducing agent .

- They reduce chromogenic agents like Benedict’s reagent or Fehling’s solution to give a colored precipitate.

- Urine is tested for the presence of reducing sugars using these colorimetric tests . *A positive result is indicative of an underlying , because sugars are not normally percent in urine* EXAMPLES: - monosaccharides. - Lactose. - Maltose. Sucrose is non-reducing, Why? Sucrose is the combination of cyclic structures of Glucose and Fructose and therefore does not have a free aldehyde or ketone group.

435 Biochemistry Team in glycop Complex Carbohydrates r-oteins and proteog -lycans Carbohydrates attached to non-carbohydrate structures by glycosidic bonds (O- or N-type). Bilirubin

Purine and pyrimidine Complex bases Carbohyd- in glyco rates in -lipids nucleic

435 Biochemistry Team Glycosidic Bonds

-It is a type of that joins a carbohydrate (sugar) .)ممكن يكون شوقر ووممكن يكون شي ثاني مثل الكومبليكس شوقرز) molecule to another group

N-Glycosidic bond O-Glycosidic bond If the group on noncarbohydrated molecule to which sugar attaches is

NH2 OH

NOTE: - All sugar-sugar glycosidic bond is: O-Glycosidic bond>

435 Biochemistry Team Result of negatively: * are large complexes of they "slip" past each other and this negatively charged produces the "slippery" consistency heteropolysaccharide chains of mucous secretions and synovial fluid

The (usually sulfated) is either D-glucosamine or D-galactosamine * are linear of repeating units [acidic sugar-amino sugar]n The acidic sugar is either D- or L-iduronic * are strongly negatively-charged: acid carboxyl groups of acidic sugars and Sulfate groups

* GAGs are associated with a small amount of forming 

proteoglycans Glycosaminoglycans (GAGs) Glycosaminoglycans

* GAGs bind with a large amounts of mucopolysaccharides  producing the gel-like matrix that forms the

435 Biochemistry Team -the original naming of these compounds mucopolysaccharides - The viscous, lubricating properties of mucous secretions also result from GAGs

the water is "squeezed When it compressed: out“, then it will be This property (smaller volume) contributes to the GAGs’ solution: resilience of synovial the GAGs spring back to fluid and the vitreous humor of the eye When the compression their original, them it will be (hydrated volume) is released: because of the repulsion of their negative charges

Members of GAGs: (examples)

Keratan sulfates: : Compared : Unlike other GAGs Chondroitin sulfates: to other GAGs, it is that are extracellular, heparin Most heterogeneous Most abundant GAG unsulfated and not covalently is intracellular and serves as GAGs attached to protein an anticoagulant

435 Biochemistry Team Carbohydrates Summary metabolism disorder Diabetes mellitus Carbohydrates: of carbon (CH2O)n Galactosemia * Abundant. * Energy storage. * Structural component of * The bond is O-glycosidic bond. classification

monosaccharide disaccharide

>10 monosaccharides It is simple sugars Joining of two Joining of (3-10) * Homopolysaccharides It is further classified monosaccharides monosaccharides - Branched: based on: * Maltose(α -1,4) = glycogen, starch * No. of carbon atoms glucose + glucose - Unbranched: Triose, , * Sucrose (α -1,2) = cellulose pentose..etc glucose + fructose * Heteropolysaccharides * Functional sugar group * Lactose (β -1,4) = glycosaminoglycans Aldoses, ketoses glucose + galactose (GAGs) 435 Biochemistry Team Monosaccharide Isomerism Complex carbohydrate: glucose and fructose Carbohydrate and non-carbohydrate Aldo-ketose ribose and ribulose attached by glycosidic bond (O- or N-) glyceraldehyde and dihydroxyacetone * Purine and pyrimidine bases. Epimers glucose and galactose C4 * Bilirubin. * . glucose and mannose C2 * and proteoglycans. D- and L- forms (Mirror image) D-glucose L-glucose * based on the position of –OH grp on the Glycosaminoglycans (GAGs): asymmetric C farthest from the carbonyl C Negatively charged heteropolysaccharides α- and β- anomers α-D-glucose β-D-glucose (acidic sugar –amino sugar)n Slippery consistency of mucous secretion * فوق β- OH / تحت α- OH and synovial fluids. Reducing sugar: Free O on the anomeric C of a sugar * Like a sponge.. This property contributes All monosaccharides to the resilience of synovial fluids and the Maltose vitreous humor of the eye. Lactose Examples: * Sucrose is non-reducing sugar 1- chondroitin sulfates 2- keratan sulfates 3- hyaluronic acid 4- heparin

435 Biochemistry Team Videos

Carbohydrates Monosaccharaides Video of disaccharide + polysaccharide Isomers Carbohydrates - cyclic structures and anomers

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