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BIOCHEMISTRY > Carbohydrate Chemistry (ppt) > Flashcards

Carbohydrate Chemistry (ppt) Flashcards

1
Q

Functions of Carbohydrates

A
  1. SOURCE
  2. INTERMEDIATES
  3. ASSOCIATED
  4. FORM
  5. PARTICIPATE
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2
Q

Simple sugars

A

MONSACCHARIDES

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3
Q

Simplest sugar

A

Trioses:
D-GLYCERALDEHYDE (Aldose)
DIHYDROXYACETONE (Ketose)

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4
Q

Is a carbon atoms attached to 4 different groups

A

CHIRAL CARBON (ASYMMETRIC CARBON)

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5
Q

All monosaccharides have chiral carbon except?

A

DIHYDROXYACETONE

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6
Q

Reference sugar

A

GLYCEROSE(GLYCERALDEHYDE)

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7
Q

the —OH group on this carbon is on the right

A

D ISOMER

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8
Q

the —OH group on this carbon is on the left

A

L ISOMER

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9
Q

Most of the naturally occurring monosaccharides are?

A

D SUGARS

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10
Q

Non mirror isomers

A

DIASTEREOISOMERS

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11
Q

Mirror image isomers

Ex: D-fructose and L-fructose

A

ENANTIOMERS

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12
Q

The presence of asymmetric carbon atoms also confers optical activity on the compound.

When a beam of plane-polarized light is passed through a solution of an optical isomer, it rotates either to the right, dextrorotatory (+), or to the left

A

OPTICAL ISOMERISM

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13
Q

-

A

DEXTROROTATORY (+)

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14
Q

-

A

LEVOROTATORY (-)

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15
Q

Measurement of optical activity in chiral or asymmetric molecules using plane polarized light

A

POLARIMETRY

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16
Q

Are the middle asymmetric carbons other than the subterminal one

Isomers differing as a result of variations in configuration of the —OH and —H on carbon atoms 2, 3, and 4 of glucose

Two sugars that differ only in the configuration around one carbon atom

A

EPIMERS

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17
Q

Important epimer of glucose

A

MANNOSE (epimerized in carbon 2)

GALACTOSE (epimerized in carbon 4)

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18
Q

A six membered ring

A

PYRAN

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19
Q

A five-membered ring

A

FURAN

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20
Q

These are isomeric forms of monosaccharides that differ only in their configuration about the hemiacetal or hemiketal carbon atom

A

ANOMERS

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21
Q

It is the carbonyl carbon atom

A

Anomeric carbon

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23
Q

These are ring structure formed by combination of an aldehyde/ketone into an alcohol group

A

HEMIACETAL/ HEMIKETAL

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24
Q

Simple ring in perspective conformational representation

A

HAWORTH PROJECTION

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25
Q

Straight chain representation

A

FISCHER PROJECTION

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26
Q

Process where CHO change spontaneosuly between the and configurations through the formation of intermediate open chain.

A

MUTAROTATION

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27
Q

Used to identify sugars

Monosaccharides reacting with phenylhydrazine

A crystalline compound with a sharp melting point and a characteristic shape is obtained

A

OSAZONE FORMATION

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28
Q

D-fructose and D-mannose give the same _ as D-glucose

A

NEEDLE SHAPE OSAZONE CRYSTALS

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29
Q

3 Types of acid formed when aldoses where oxidized:

A

ALDONIC ACID
URONIC ACID
SACCHARIC ACID

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30
Q

Aldehyde group is converted to a carboxyl group

Examples:
Glucose – Gluconic acid, Galactose-Galactonic acid and Mannose- Mannonic acid

A

ALDONIC ACID

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31
Q

Aldehyde is left intact and primary alcohol at the other end is oxidized to COOH

Examples:
Glucose — Glucuronic acid
Galactose — Galacturonic acid
Mannose—–Mannuronic acid

A

URONIC ACID

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32
Q

Oxidation at both ends of monosaccharide

Examples:
Glucose —- Gluco saccharic acid
Galactose — Mucic acid
Mannose — Mannaric acid

A

SACCHARIC ACID (GLYCARIC ACID)

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33
Q

-

A

REDUCTION

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34
Q

Resultant product when a sugar is reduce

A

POLYOL (SUGAR ALCOHOL)

GLUCOSE - GLUCITOL
MANNOSE - MANNITOL
FRUCTOSE - MANNITOL AND SORBITOL
GLYCERALDEHYDE - GLYCEROL

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35
Q

Monosaccharides are normally stable to dilute acids, but are dehydrated by?

A

STRONG ACIDS

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36
Q

D-ribose when heated with concentrated HCl yields?

A

FURFURAL

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37
Q

Forms the basis of Molisch test, Seliwanoff test and Bial’s Test

A

DEHYDRATION OF STRONG ACIDS ON MONOSACCHARIDES.

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38
Q

Highly reactive sugars

Powerful reducing agents

Allows interconversion of D-mannose, D-fructose and D-glucose

A

ENEDIOLS

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39
Q

Interconversion reaction of D-mannose, D-fructose and D-glucose

A

LOBRY DE BRUYN-VAN ECKENSTEIN TRANSFORMATION

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40
Q

This happens when sugar is reacted to strong alkalis (decomposition)

A

CARAMELISATION

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41
Q

Enediols obtained by the action of bases are quite susceptible to oxidation when heated in the presence of an oxidising agent. It forms the basis of _ for the detection of reducing sugars

A

BENEDICT’S AND FEHLING’S TEST

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42
Q

Frequently used as the oxidising agent and a red precipitate of Cu2O is obtained

A

COPPER SULFATE

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43
Q

Sugars which give a reaction with copper sulfate and forming a red precipitate of Cu2O.

A

REDUCING SUGARS

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44
Q

Fehling’s solution

A

KOH or NaOH and CuSO4

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45
Q

Benedict’s solution

A

Na2CO3 and CuSO4

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46
Q

They are formed by replacing the hydroxyl group (at C2 usually) of monosaccharides by amino group

A

AMINO SUGARS

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47
Q

The most common amino sugars

A

GLUCOSAMINE and GALACTOSAMINE

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48
Q

Amino sugar present in Heparin, Hyaluronic acid and blood group substances

A

GLUCOSAMINE

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49
Q

Amino sugar present in Chondroitin of cartilages and tendons.

A

GALACTOSAMINE

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50
Q

The amino group may be condensed with active acetate forming?

They are components of glycosaminoglycans and some glycosphingolipids (lipids)

Component of CHITIN

A

N-ACETYL GLUCOSAMINE

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51
Q

Amino sugar that is a component of glycoproteins and gangliosides(Lipids) of cell membrane.

A

N-ACETYL MANNOSAMINE

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52
Q

Component of Chondroitin sulphate.

A

N-ACETYL GALACTOSAMINE

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53
Q

Amino sugar acids are produced by?

A

CONDENSATION OF AMINO SUGAR WITH PYRUVIC OR LACTIC ACID

54
Q

Amino sugar acid produced by the condensation of lactic acid with D- Glucosamine

A

MURAMIC ACID

55
Q

An amino sugar acid that is formed from the condensation of pyruvic acid with N-Acetyl Mannosamine

A

N-AACETYL NEURAMINIC ACID

56
Q

Sugars that are formed by removal of an oxygen atom usually from 2nd carbon atom

A

DEOXY SUGARS

57
Q

Deoxy sugar is which is the sugar found in DNA

A

2’-DEOXY RIBOSE

58
Q

A deoxy sugar used as a fermentative reagent in bacteriology

A

6-DEOXY-L-MANNOSE (L-RHAMNOSE)

59
Q

Are formed by the oxidation of aldehyde C1(Aldonic acid)

  • or terminal hydroxyl group at C6 of aldose sugar(uronic acid)
  • or both (saccharic) to form carboxylic group.
  • Glucuronic and Iduronic acids are the components of glycosaminoglycans.
  • L-ascorbic acid(vitamin C) is a sugar acid.
A

SUGAR ACIDS

60
Q

A sugar acid involved in detoxification of bilirubin and other foreign compounds.

A

GLUCURONIC ACID

61
Q

Are formed by the reduction of the carbonyl group (aldehyde or ketone) of monosaccharide

A

SUGAR ALCOHOLS

62
Q 
Give the reduction form of the following sugars into sugar alcohol:
Glucose
Mannose
Fructose
Galactose
Ribose
A 
Respectively:
SORBITOL
MANNITOL
SORBITOL/ MANNITOL
DULCITOL/ GALACTITOL
RIBITOL (Vitamin B2)
63
Q

Hydroxyl groups of sugars can be esterified to form Acetates, phosphates, benzoates etc.

Sugars are phosphorylated at terminal C1 hydroxyl group or at other places

At terminal hydroxyl: Glucose-6-Phosphate or Ribose-5-Phosphate

A

SUGAR ESTERS

64
Q

Metabolism of sugars inside the cell starts with?

A

PHOSPHORYLATION

65
Q

Also components of nucleosides and nucleotides.

A

SUGAR PHOSPHATES

66
Q

Formed by the reaction of the -OH group of anomeric carbon (hemiacetal or hemiketal) with the hydroxyl group of any other molecule with the elimination of water.

A glycosidic bond is formed.

A

GLYCOSIDES

67
Q

These include derivatives of digitalis and strophanthus such as oubain.

A

CARDIAC GLYCOSIDES

68
Q

A glycoside that is use as an antibiotic

A

STREPTOMYCIN

69
Q

A glycoside that displaces Na+ from the binding sites of “carrier protein” and prevents the binding of sugar molecule and produces glycosuia

A

PHLORIDZINE

70
Q

Sugars composed of two monosaccharide residues link by glycosidic bond

A

DISACCHARIDES

71
Q

Formed by joining of 2 glucose units by alpha-1,4 glycosidic bond
- O-α-D-glucopyranosyl-(1->4)- α -D-glucopyranose

Produced by partial hydrolysis of starch either by Salivary or Pancreatic amylase

Fermentable sugar

Used as nutrient as a sweetener and as a fermentative reagent

Has a free active group and hence exhibits reducing properties, mutarotation and α-β isomerism.

A

MALTOSE (MALT SUGAR)

72
Q

Composed of 2 glucose units linked by alpha-1,6 glycosidic linkage

Produced by enzymatic hydrolysis of starch (at the

A

ISOMALTOSE

73
Q

Non reducing sugar

O-α-D-glucopyranosyl-(1->2)-β-D-fructofuranoside
-the configuration of this glycosidic linkage is α for glucose and β for fructose.

No free reactive group (because the anomeric carbons of both monosaccharides units are involved in the glycosidic bond)

Neither shows reducing properties nor mutarotation characters

Invert sugar

A

SUCROSE (TABLE SUGAR)

74
Q

Hydrolytic product of Sucrose is called? Because the optical activity of sucrose ( dextrorotatory) is inverted after hydrolysis [by an acid or an enzyme (invertase or sucrase)] into equimolar mixture of its two components glucose (+52.5) and fructose (-92.5) and the optical activity of the mixture becomes levorotatory.

A

INVERT SUGAR

75
Q

Enzyme that cleave sucrose into its component monosaccharides

A

SUCRASE

76
Q

Galactose + Glucose via β (1,4) glycosidic linkage

Sugar of milk

Syntesized in the mammary glands during lactation

Milk contains the alpha and beta anomers in a 2:3 ratio

Used in infant formulations, medium for penicillin production and as diluent in pharmaceuticals

A

LACTOSE

77
Q

Is sweeter and more soluble than ordinary α - lactose

A

BETA LACTOSE

78
Q

Enzyme that catalyze the hydrolysis of lactose to its monosaccharide components.

A 
LACTASE (Human)
BETA GALACTOSIDASE (Bacteria)
79
Q

Deficiency of lactase enzyme that is manifested by diarrhea, abdominal cramps, bloating and distension

A

LACTOSE INTOLERANCE

80
Q

Composed of beta-galactose and beta-fructose in a beta-(1,4) glycosidic bond

Semi-synthetic disaccharide

Osmotic laxative

Management of portal systemic encephalopathy

Use to lower the high ammonia content i chronic liver disease

A

LACTULOSE

81
Q

O-alpha-D-glucopyranosyl-1->)-alpha-D-glucopyranoside

Found in yeast and fungi

The main sugar of insect hemolymph

Non reducing in nature due to lack of free functional group

A

TREHALOSE

82
Q

-

A

OLIGOSACCHARIDES

83
Q

Trisaccharide

Glucose + Galactose + Fructose

A

RAFFINOSE

84
Q

Tetrasaccharide

2 Galactose + Glucose + Fructose

A

STACHYOSE

85
Q

Pentasaccharide

3 Galactose + Glucose + Fructose

A

VERBASCOSE

86
Q

Hexasaccharide

4 Galactose + Glucose + Fructose

A

AJUGOSE

87
Q

Sugar constituent of honey

A

MELEZITOSE

88
Q

A break down product of starch useful in chromatographic separation

A

CYCLOHEPTAMYLOSE (HEPETASACCHARIDE)

89
Q

Characteristics:

Polymers (MW from 200,000)
White and amorphous products (glassy) 
Not sweet
Not reducing; do not give the typical aldose or
ketose reactions
Form colloidal solutions or suspensions
A

POLYSACCHARIDE/ GLYCAN

90
Q

2 Types of Polysaccharides:

A

HOMOGLYCANS

HETEROGLYCANS

91
Q

Examples of Homoglycans:

💡💡
G
 S
 C
 G
F
 I
A

GLUCOSANS:
Starch
Cellulose
Glycogen

FRUCTOSAN:
Inulin

GALACTOSAN
Agar

92
Q

Example of Heteroglycans:

A

MUCOPOLYSACCHARIDES

93
Q

These are polymers composed of a 💡single type of sugar monomers

A

Homopolysaccharides/ Homoglycans

94
Q

Also known as 💡animal starch
Stored in 💡muscle and liver
Present in cells as granules (high MW)
Contains both 💡α(1,4) links and 💡α(1,6) branches at every 8 to 12 glucose unit
Complete hydrolysis yields glucose
With iodine gives a 💡red-violet color
Hydrolyzed by both α and 💡β-amylases and by 💡glycogen phosphorylase
Serves as a 💡buffer to maintain blood glucose level.

A

GLYCOGEN

95
Q

The concentration of glycogen is __ in the liver than in muscle (10% versus 2% by weight), but more glycogen is stored in skeletal muscle overall because of its much greater mass.

A

HIGHER

96
Q

It is the most common storage polysaccharide in 💡plants

Composed of 10 – 30% Amylose and 70-90% amylopectin depending on the source

A

STARCH

97
Q

A linear polymer of α-D-glucose, linked together by 💡α 1→4 glycosidic linkages.
It is soluble in water, reacts with iodine to give a 💡blue color and the molecular weight of ranges between 50,000 – 200,000.

A

AMYLOSE

98
Q

A highly branched polymer, 💡insoluble in water, reacts with iodine to give a 💡reddish violet color. The molecular weight ranges between 70,000 - 1,000,000.

Branches are composed of 💡25-30 glucose units linked by 💡α 1→4 glycosidic linkage in the chain and by 💡α 1→6 glycosidic linkage at the branch point.

A

AMYLOPECTIN

99
Q

Examples of storage polysaccharide:

A

STARCH
GLYCOGEN
INULIN

100
Q

Suspensions of Amylose in water adopt a __.

A

HELICAL CONFORMATION

101
Q

It can insert in the middle of the Amylose helix to give a 💡blue color that is characteristic and diagnostic for starch

A

IODINE

102
Q

Produced by the 💡partial hydrolysis of starch along with maltose and glucose

Used as 💡mucilages (glues)

Used in 💡infant formulas (prevent the curdling of milk in baby’s stomach)

Used as 💡thickening agents in food processing.

A

DEXTRINS

103
Q

Dextrins are often referred to as either;

A

Amylodextrins
Erythrodextrins
Achrodextrins

104
Q

Products of the reaction of glucose and the enzyme 💡transglucosidase from Leuconostoc mesenteroides

Contains 💡α (1,4), 💡α(1,6) and 💡α (1,3) linkages

Used as 💡plasma expanders (treatment of shock)

Used as 💡molecular sieves to separate proteins and other large molecules (gel filtration chromatography)

Components of 💡dental plaques

A

DEXTRANS

105
Q

Polymer of β-D-glucose linked by 💡β(1,4) linkages

Yields glucose upon complete hydrolysis

Partial hydrolysis yields 💡cellobiose

Most 💡abundant of all carbohydrates

Gives no color with iodine
Cellulose is tasteless, odorless and insoluble in water and most organic solvents.

Cannot be hydrolyze by mammals because it lacks the enzyme that hydrolyzes the 💡β 1→ 4 bonds

It is an important source of “bulk” in the diet, and the major component of dietary fiber.

A

CELLULOSE

106
Q

It is used as binder-disintegrant in tablets

A

Microcrystalline cellulose

107
Q

Suspending agent and bulk laxative

A

Methylcellulose

108
Q

Hemostat

A

Oxidized cellulose

109
Q

Laxative

A

Sodium carboxymethyl cellulose

110
Q

rayon; photographic film; plastics

A

Cellulose acetate

111
Q

enteric coating (capsules)

A

Cellulose acetate phthalate

112
Q

explosives; collodion (pyroxylin)

A

Nitrocellulose

113
Q

Examples of Structural Polysaccharide

A

CELLULOSE

CHITIN

114
Q

The second most abundant carbohydrate polymer of 💡N- Acetyl Glucosamine

Present in the 💡cell wall of fungi and in the 💡exoskeletons of crustaceans, insects and spiders

Used commercially in coatings (extends the shelf life of fruits and meats)

A

CHITIN

115
Q

💡β-(1,2) linked fructofuranoses
Linear ,no branching
Lower molecular weight than starch
Colors yellow with iodine
Hydrolysis yields 💡fructose
Sources include onions, garlic, dandelions and Jerusalem artichokes
Used as diagnostic agent for the evaluation of 💡glomerular filtration rate (renal function test)

A

INULIN

116
Q

Uses of Inulin:

💡💡
G
DF
AS
LGIS
F/C S
A 
Used clinically as a highly accurate measure of
glomerular filtration rate (GFR)
Used as a soluble dietary fiber
Used as appetite suppressant
Used as a low glycemic index sweetener 
Also used as a fat/cream substitute
117
Q

A 💡galactose polymer
Obtained from the cell walls of some species of 💡red algae or seaweeds (Sphaerococcus Euchema ) and species of Gelidium
Dissolved in hot water and cooled, agar becomes gelatinous;
Its chief use is as a 💡culture medium for microbiological work. Other uses are as a 💡laxative,
A 💡vegetarian gelatin substitute,
A thickener for soups, in jellies, ice cream and Japanese desserts, As a clarifying agent in brewing, and for sizing fabrics.

A

AGAR

118
Q

Are carbohydrates containing a repeating disaccharide

The disaccharide usually contains an acid sugar and an amino sugar.

Acid sugar is generally 💡D- Glucuronic acid or its 💡C-5 epimer Iduronic acid, while amino sugar is either 💡D- Glucosamine or 💡D-Galactosamine, amino group is generally acetylated eliminating its positive charge.
The amino sugar may be sulfated on non acetylated nitrogen.
Carboxyl groups of acid sugars together with sulfate groups give Glycosaminoglycans 💡strongly negative nature.

A

Heteropolysaccharides/ Mucopolysaccharides/ Glycosaminoglycans

119
Q

Occurrence: synovial fluid, ECM of loose connective tissue.
Serves as a lubricant and shock absorber.
Only GAG that 💡does not contain any sulfate and is 💡not found covalently attached to proteins.
It forms non-covalently linked complexes with Proteoglycans in the ECM.
Are very large (100 - 10,000 kDa) and can displace a large volume of water.

A

Hyaluronic acid (💡D-glucuronate + GlcNAc)n

120
Q

skin, blood vessels, heart valves

💡(L-Iduronate + GalNAc sulfate)n

A

Dermatan sulfate

121
Q

Occurrence: cartilage, tendons, ligaments, heart valves and aorta.

It is the 💡most abundant GAG.

💡(D-glucuronate + GalNAc sulfate)n

A

Chondroitin sulfate

122
Q

Component of intracellular granules of mast cells lining the arteries of the lungs, liver and skin

Contrary to other GAGs that are extra cellular compounds, it is intracellular.

💡(D-glucuronate sulfate + N-sulfo-D-glucosamine)n

Acts as an 💡anticoagulant.

A

Heparin

123
Q

Occurrence: cornea, bone, cartilage;
They are often aggregated with Chondroitin sulfates.

💡(Gal + GlcNAc sulfate) n

A

Keratan sulfate

124
Q

Found in 💡Pneumococci capsule

Act as 💡blood group substances.

Four monosaccharides , Galactose, Fucose, Galactosamine(Acetylated) and Acetylated Glucosamine are present in all types of blood group substances.

Also found in egg protein- ovalbumin

A

Neutral Mucopolysaccharides

125
Q

Formed of 💡glycosaminoglycans (GAGs) covalently attached to the 💡core proteins.

Found in all connective tissues, extracellular matrix (ECM) and on the surfaces of many cell types.

Remarkable for their 💡diversity

A

Proteoglycans (mucoproteins)

126
Q

A Proteoglycan monomer found in cartilage consists of a __

A

core protein to which the linear GAG chains are covalently linked.

127
Q

The proteoglycan monomers associate with a molecule of Hyaluronic acid to form __

Bottle brush

A

Proteoglycan aggregates

128
Q

Biophysical functions of Proteoglycans:

💡💡
C ECM
I CE
T ECM
B
L
CM
GFR
AC
SS
TC
A

Act as constituent of extracellular matrix or ground substance

Interact with collagen and Elastin

Contribute turgor to ECM acting as polycations and attracting water.

Act as barrier in the tissues

Act as lubricant in the joints

Help in the release of hormones

Help in cell migration in embryonic tissues

Present in the basement membrane of glomerulus of kidney, play important role in the Glomerular filtration

Heparin acts as an anticoagulant .
Heparin helps in the release of lipoprotein lipase, also called ‘Clearing factor’.

Components of cell membrane, act as receptors.

Chondroitin sulfates and hyaluronic present in cartilages have a great role in compressibility of cartilage in weight bearing

Maintain shape of sclera

Help in maintaining the transparency of cornea

129
Q

Biochemical functions of Proteoglycans:

A

Participate in cell and tissue development and physiology.

130
Q

D-glucose when heated with concentrated HCl yields?

A

5-HYDROXYMETHYLFURFURAL

BIOCHEMISTRY (11 decks)

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