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Biochemistry > Module 08: Carbohydrates (Stoker) > Flashcards

Module 08: Carbohydrates (Stoker) Flashcards

1
Q

This is the study of the chemical substances found in living organisms and the chemical interactions of these substances with each other

A

Biochemistry

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2
Q

This is a chemical substance found within a living organism

A

biochemical substance

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3
Q

This form of biochemical substance are comprised of water and inorganic salts.

A

Bioinorganic substances

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4
Q

This form of biochemical substance are comprised of carbohydrates, lipids, proteins, and nucleic acids

A

Bioorganic substances

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5
Q

How many percentage of dry plant material is produced by photosynthesis?

A

75%

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6
Q

This is the structural element of carbohydrates?

A

Cellulose

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7
Q

This is the energy reservoir of the body and is present in small amounts.

A

Starch/glycogen

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8
Q

The average human diet contains how many carbohydrates?

A

2/3 of carbohydrates

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9
Q

Carbohydrates are also known as what

A

Saccharides (is perceived as the most abundant bioorganic molecules on Earth)

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10
Q

How are carbohydrates produced?

A

Produced by photosynthesis

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11
Q

What is the general formula of carbohydrates?

A

(CH2O)n (n≥3)

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12
Q

What are the functions of carbohydrates?

A

(1) Carbohydrate oxidation - provides energy
(2) Carbohydrate storage, in the form of glycogen, provides a short-term energy reserve
(3) Carbohydrates supply carbon atoms for the synthesis of other biochemical substances (proteins, lipids, and nucleic acids)
(4) Carbohydrates form part of the structural framework of DNA and RNA molecules
(5) Carbohydrates linked to lipids (Chapter 19) are structural components of cell membranes
(7) Carbohydrates linked to proteins (Chapter 20) function in a variety of cell–cell and cell–molecule recognition processes

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13
Q

When integrated with lipids, carbohydrates act as “_________________-“

A

structural components of cell membranes

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14
Q

When integrated with proteins, carbohydrates act as “_________________-“

A

function in a variety of cell–cell and cell–molecule recognition processes

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15
Q

What is the simpler formula of carbohydrates?

A

CnH2nOn or Cn(H2O)n (hydrates of C), where n pertains to the number of atoms

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16
Q

In plants, these serve as structural elements in the cell wall of plants

A

Cellulose

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17
Q

in plants, these serve as energy reserve for plants

A

Starch

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18
Q

Carbohydrates are classified as either what?

A

polyhydroxy aldehydes or ketones

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19
Q

How do some carbohydrates produce such substances?

A

Hydrolysis

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20
Q

These contain single polyhydroxy aldehyde or ketone unit. They cannot be broken down into simpler substances by hydrolysis (reaction with water) reactions

A

Monosaccharide

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21
Q

How many carbon atoms do Monosaccharides contain?

A

Contains 3 to 7 C atoms, where 5 and 6 carbon species are more common

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22
Q

How are Monosaccharides classified?

A

They are water-soluble white crystalline solids

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23
Q

What are examples of Monosaccharides?

A

Glucose and Fructose

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24
Q

These contain 2 monosaccharide units and are classified to be more common and are also crystalline water soluble substances.

A

Disaccharides

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24
Q

What do Disaccharides form when hydrolyzed?

A

2 monosaccharide units

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25
Q

These are generic examples of Disaccharides?

A

Table sugar (sucrose) and milk sugar (lactose)

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26
Q

In the human body, Disaccharides function as what?

A

In human body, Disaccharides are associated with proteins and lipids for structural and regulatory functions

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27
Q

These contains 2 to 10 monosaccharide units that are covalently bonded to each other

A

Oligosaccharides

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28
Q

These contains many monosaccharide units that are covalently bonded.

A

Polysaccharides

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29
Q

These Polysaccharides may contain 100s of 1000s of monosaccharide units.

A

Polymers

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30
Q

These are generic examples of Polysaccharides?

A

Cellulose and Starch

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31
Q

Most monosaccharides exist in two forms:

A

(1) Left-handed
(2) Right-handed

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32
Q

These types of objects are defined as images that coincide at all points when the images are laid upon each other

A

Superimposible on their mirror images (achiral)

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33
Q

These types of objects are characterized to be Chiral (handedness).

A

Non-superimposable on their mirror images

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34
Q

How do you define a chiral center?

A

C atom attached to 4 different groups (A molecule with chiral center is a chiral molecule )

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35
Q

How do you classify chirality?

A

(1) Best way to visualize - look at all C atoms and see if there are at least two H atoms then that can’t be a chiral center
(2) C atoms with less than one H atoms are worth looking at for their chirality
(3) similarity and difference of groups

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36
Q

Why is 3-bromopentane achiral?

A

C has two CH2-CH3 groups – so it is achiral

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37
Q

What are the responses of Left and Right Handed Forms of a Molecule in a Human Body?

A

(1) Both may be active, one may be more active or one may be active and other non-active
Example: Right handed hormone epinephrine is 20 times more active than left handed form
(2) Almost all monosaccharides are right handed
(3) Amino acids are almost always left handed

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38
Q

Where are Monosaccharides derived from?

A

Derived from CO2 and H2O by photosynthesis

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39
Q

How are Monosaccharides classified?

A

(A( their carbonyl group: aldehydes (aldose) or ketones (ketose)
(B) the number of C (trioses, tetroses, pentoses, hexoses, heptose)
(C) According to configuration – D or L sugar

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40
Q

This is known as the smallest aldose.

A

Glyceraldehyde

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41
Q

This is known as the smallest ketose

A

Dihydroxy-acetone

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42
Q

How many chiral carbons does aldohexose d-glucose have?

A

four (4) chiral carbons

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43
Q

These have the same absolute configuration at the asymmetric center farthest away from their carbonyl group as does D-glyceraldehyde (i.e., C5 in D glucose).

A

D sugars

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44
Q

How many asymmetric center does Glyceraldehyde have?

A

one asymmetric center

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45
Q

How did Emil Fischer propose spatial isomers (Stereoisomers)?

A

In 1892, Emil Fisher proposed that the spatial isomers (stereoisomers), of glyceraldehyde be designated D- and L-glyceraldehyde. Fisher assigned the D and L to the above structures of glyceraldehyde, but it was not until 1949 that experiments confirmed that his guess was correct.

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46
Q

What do D-isomers denote?

A

D indicates rotation to the right

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47
Q

What do L-isomers denote?

A

L indicates rotation of polarized light to the left. The L sugars are the mirror images of their D counterparts

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48
Q

This pertains to the monosaccharide with an aldehyde group on C1

A

Aldose

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49
Q

This pertains to the monosaccharide with a keto group on C2

A

Ketose

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50
Q

These are isomers that have the same molecular and structural formulas but differ in the orientation of atoms in space.

A

Stereoisomers

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51
Q

These are stereoisomers whose molecules are nonsuperimposable mirror images of each other. Molecules with chiral center.

A

Enantiomers

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52
Q

These are stereoisomers whose molecules are not mirror images of each other.

A

Diastereomers

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53
Q

This is a method for giving molecular chirality specifications in two dimensions

A

Fischer projection formulas

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54
Q

How are Fischer projection formulas characterized?

A

This is a two-dimensional structural notation for showing the spatial arrangement of groups about chiral centers in molecules.

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55
Q

In a Fischer projection formula, how is a chiral center (Carbon) represented?

A

as the intersection of vertical and horizontal lines

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56
Q

In a Fischer projection formula, D and L system are used to what

A

D and L system used to designate the handedness of glyceraldehyde enantiomers can be extended to other monosaccharides with more than one chiral center

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57
Q

These has four groups attached to the atom at the chiral center

A

tetrahedral geometry (Tetrahedral Arrangements)

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58
Q

In Tetrahedral Arrangements, what do vertical arrangements represent?

A

represent bonds to groups directed into the printed page.

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59
Q

In Tetrahedral Arrangements, what do horizontal arrangements represent?

A

represent bonds to groups directed out of the printed page

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60
Q

Where should one start numbering a carbon chain?

A

starting at the carbonyl group end of the molecule

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61
Q

What is used to determine D or L configuration?

A

highest-numbered chiral center

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62
Q

These are diastereomers whose molecules differ only in the configuration at one chiral center

A

Epimers

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63
Q

How do Constitutional isomers and Diastereomers differ?

A

in most chemical and physical properties.(boiling points and melting points)

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64
Q

How are enantiomers different?

A

(1) Their interaction with plane polarized light
(2) Their interaction with other chiral substances

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65
Q

In this property of light, these form light move in all directions

A

Ordinary (unpolarized) Light

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66
Q

In this property of light, these form light move in same (comparable) and in one direction.

A

Plane polarized Light

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67
Q

How is a Plane polarized Light rotated?

A

Plane polarized light is rotated clockwise (to right) or counterclockwise (to left) when passed through enantiomers (Direction and extent of rotation will
depend upon the enantiomer)

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68
Q

How do same concentration of two enantiomers rotate?

A

rotate light to same extent but in opposite direction (optically active)

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69
Q

This is a chiral compound that rotates light towards right (clockwise; +)

A

Dextrorotatory

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70
Q

This is a chiral compound that rotates light towards left (counterclockwise; -)

A

Levorotatory

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71
Q

How are D and L as well as + and - determined, respectively?

A

Structure and by using a polarimeter

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72
Q

How is the solubility of achiral solvents enantiomeric pairs characterized?

A

Enantiomeric pairs have same solubility in achiral solvents like ethanol

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73
Q

How is the solubility of chiral solvents enantiomeric pairs characterized?

A

Enantiomeric pairs have different solubility in chiral solvent like D-2-butanol

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74
Q

The comparable (similar) boing points melting points, and densities of enantiomers are dependent on what

A

intermolecular forces and chirality doesn’t depend on them

75
Q

This classification of monosaccharides contains three carbon atoms.

A

Triose

76
Q

This classification of monosaccharides contains four carbon atoms.

A

Tetrose

77
Q

This classification of monosaccharides contains five carbon atoms.

A

Pentoses

78
Q

This classification of monosaccharides contains six carbon atoms.

A

Hexoses

79
Q

This is a monosaccharide with aldehyde group and 6 C atoms

A

D-Glucose (Aldohexose)

80
Q

This is a monosaccharide with ketone group and 6 C atoms

A

D-Fructose (Ketohexose)

81
Q

This is an optimal source of glucose.

A

Grape fruit, grape sugar, dextrose, and blood sugar (70 - 100 mg/100 mL of blood)

82
Q

This is the most abundant in nature and is nutritionally most important

A

Glucose

83
Q

How much glucose can be obtained from grapefruit?

A

20-30% by mass

84
Q

Glucose is characterized as a What?

A

Six membered cyclic form )Aldohexose)

85
Q

This is the sweetest tasting of all sugars, found in many fruits and in honey is also perceived as a good dietary sugar due to higher sweetness

A

Fructose

86
Q

fructose is characterized as a What?

A

Six membered cyclic form Ketohexose)

87
Q

This is known as the milk sugar and is synthesized by humans. It is also utilized to differentiate between blood types.

A

Galactose

88
Q

Galactose is also known as “__________-“

A

brain sugar (part of the brain and nerve tissue)

89
Q

Galactose is characterized as a What?

A

Six membered cyclic form )Aldohexose)

90
Q

Ribose is a part of what?

A

(1) ATP
(2) DNA
(3) RNA

91
Q

Ribose is characterized as a What?

A

Five membered cyclic form (Aldopentose)

92
Q

This is the dominant form of monosaccharides with 5 or more C atoms.

A

Cyclic Hemiacetal Forms of D-Glucose

93
Q

How are cyclic forms in equilibrium?

A

cyclic forms are in equilibrium with open chain form

94
Q

How are cyclic forms formed (generated)?

A

Cyclic forms are formed by the reaction of carbonyl group (C=O) with hydroxyl (-OH) group on carbon 5

95
Q

What is the alpha form of d-glucose?

A

Alpha-form: -OH of C1 and CH2OH of C5 are on opposite sides

96
Q

What is the beta form of d-glucose?

A

OH of C1 and CH2OH of C5 are on same sides

97
Q

What kind of isomerism is observed in aldose and ketose pair?

A

Functional isomers-

98
Q

What are some examples of epimers?

A

glucose and mannose, glucose and galactose

99
Q

How does D-glucose and D-Mannose differ?

A

epimer at C2

100
Q

How does D-Glucose and D-Galactose?

A

epimer at C4

101
Q

All aldoses with five or more carbon atoms establish similar equilibria, but with different percentages of the _______________.

A

alpha, beta, and open-chain forms.

102
Q

This pertains to a cyclic monosaccharide containing a six-atom ring

A

Pyranose

103
Q

This pertains to a cyclic monosaccharide containing a five-atom ring

A

Furanose

104
Q

This is a two-dimensional structural notation that specifies the three-dimensional structure of a cyclic form of a monosaccharide

A

Haworth projection formula

105
Q

How is alpha and beta configuration determined?

A

Alpha or Beta configuration is determined by the position of the —OH group on C1 relative to the CH2OH group that determines D or L series.

106
Q

How are the positions of the OH group on C1 relative to the CH2OH group in the Beta Configuration?

A

both of these groups point in the same direction

107
Q

How are the positions of the OH group on C1 relative to the CH2OH group in the Alpha Configuration?

A

the two groups point in opposite directions.

108
Q

How is the specific identity of a monosaccharides determined?

A

by the positioning of the other —OH groups in the Haworth projection formula.

109
Q

How is the OH group at a chiral center that is to the right in a Fischer projection formula pointed in the Haworth projection?

A

Down

110
Q

How is the OH group at a chiral center that is to the left in a Fischer projection formula pointed in the Haworth projection?

A

Up

111
Q

What are the five most important reactions of monosaccharides?

A

Oxidation to acidic sugars
Reduction to sugar alcohols
Glycoside formation
Phosphate ester formation
Amino sugar formation

112
Q

What are examples of aldonic acids?

A

Benedict’s, Fehling’s, Barfoeds and Tollens reagent

113
Q

This form of oxidation to sugar acids involve enzymes/

A

alduronic acid

114
Q

This form of oxidation to sugar acids involve a strong oxidizing agent (HNO3)-

A

aldaric acid

115
Q

The redox chemistry of monosaccharides in terms of the oxidation of acidic sugar is closely linked to what? .

A

the alcohol and aldehyde functional groups present in them

116
Q

Weak oxidizing agents such as Tollens and Benedict’s solutions oxidize what?

A

oxidize the aldehyde end to give an aldonic acid.

117
Q

This is a carbohydrate that gives a positive test with Tollens and Benedict’s solutions.

A

reducing sugar

118
Q

What can a reducing sugar do?

A

A reducing sugar reduces the oxidizing agent and is oxidized to an acid.

119
Q

How can Monosaccharides be oxidized>

A

Monosaccharides can be oxidized by weak oxidizing agents such as Cu2+ ions.

120
Q

What kind of acid is d-gluconate?

A

aldonic acid

121
Q

What is oxidized by strong oxidizing agents?

A

Strong oxidizing agents like concentrated nitric acid can oxidize both ends of a monosaccharide at the same time (the carbonyl group and the terminal primary alcohol group)

122
Q

What is produced upon oxidizing both ends of a monosaccharide at the same time (the carbonyl group and the terminal primary alcohol group)?

A

dicarboxylic acid:

123
Q

Aldaric acids are known as “_______________”

A

polyhydroxy dicarboxylic acids

124
Q

How is alduronic acid produced

A

In biochemical systems enzymes can oxidize the primary alcohol end of an aldose such as glucose, without oxidation of the aldehyde group, to produce an alduronic acid.

125
Q

How are sugars reduced?

A

The carbonyl group in a monosaccharide (either an aldose or a ketose) is reduced to a hydroxyl group using hydrogen as the reducing agent.

126
Q

What is the product of the reduction to sugar alcohols?

A

The product is the corresponding polyhydroxy alcohol

127
Q

This is used as moisturizing agents in foods and cosmetics and as a sweetening agent in chewing gum

A

Sorbitol

128
Q

Cyclic forms of monosaccharides are called “___________”

A

hemiacetals (they react with alcohols to form acetals)

129
Q

Monosaccharide acetals are called “______________”

A

glycoside

130
Q

How are glycosides formed?

A

A glycoside is an acetal formed from a cyclic monosaccharide by replacement of the hemiacetal carbon —OH group with an —OR group:

For example:
A glycoside produced from glucose - glucoside
A glycoside produced from galactose – galactosidase

131
Q

What are the four blood types?

A

A, B, AB, and O:

132
Q

What happens when the wrong blood is transfused?

A

A transfusion of wrong blood type can cause the blood cells to form clumps - a potentially fatal reaction.

133
Q

They are universal donors.

A

People with type O blood

134
Q

They are universal recipients.

A

People with type AB blood

135
Q

What are the most common blood types in the United States?

A

In the United States type O blood is the most common and type A the second most common.

136
Q

What is the biochemical basis for various blood types?

A

The biochemical basis for the various blood types involves monosaccharides present on plasma membranes of red blood cells.

137
Q

What is the importance of monosaccharides in blood groups?

A

The monosaccharides responsible for blood groups are D-galactose and its derivatives.

138
Q

What is formed when the hydroxyl groups of a monosaccharide react with inorganic oxyacids to form inorganic esters?

A

Phosphate ester

139
Q

When are Phosphate ester stable?

A

When they are in aqueous solution and play important roles in the metabolism of carbohydrates.

140
Q

These are important building blocks of polysaccharides such as chitin

A

Amino sugars and their N-acetyl derivatives

141
Q

One monosaccharide can act as what?

A

hemiacetal and other as alcohol

142
Q

This is produced as an intermediate in the hydrolysis of the polysaccharide cellulose:

A

Cellobiose

143
Q

Cellobiose contains what?

A

two b - D-glucose monosaccharide units linked through a b (1—4) glycosidic linkage.

144
Q

Why can’t cellobiose be digested properly?

A

Because humans do not have enzymes that can break (1-4) linkages of cellobiose

145
Q

This is digested easily by humans because we have enzymes that can break a (1-4) linkages

A

Maltose

146
Q

Lactose is made up of what?

A

b-D-galactose unit and a b-D-glucose unit joined by a b(1-4) glycosidic linkage

147
Q

This is the principal carbohydrate in milk.

A

Lactose

148
Q

How much lactose constitutes humans?

A

7%–8% lactose

149
Q

How much lactose constitutes cow’s milk?

A
  • 4%–5% lactose
150
Q

This is a condition in which people lack the enzyme lactase needed to hydrolyze lactose to galactose and glucose.

A

Lactose intolerance

151
Q

This hydrolyzes b(1-4) glycosidic linkages.

A

Lactase

152
Q

What causes the Deficiency of lactase?

A

Deficiency of lactase can be caused by a genetic defect, physiological decline with age, or by injuries to intestinal mucosa.

153
Q

What happens when lactase is not digested properly?

A

it attracts water causing fullness, discomfort, cramping, nausea, and diarrhea. Bacterial fermentation of the lactose further along the intestinal tract produces acid (lactic acid) and gas, adding to the discomfort

154
Q

This is the most abundant of all disaccharides and found in plants. It is produced commercially from the juice of sugar cane and sugar beets.

A

Sucrose (table sugar):

155
Q

How much sucrose does sugar cane contain?

A

20% by mass

156
Q

How much sucrose does sugar beet contain?

A

17% by mass sucrose

157
Q

These are formed from monosaccharide units bonded with glycosidic linkages

A

Polymers

158
Q

What are the two types of polymer chain?

A

Linear and branched, homo- and hetero-polysaccharides

159
Q

Why don’t Polysaccharides show positive tests with Tollen’s and Benedict’s solutions?

A

They are not sweet and they have limited water solubility.

160
Q

What are some examples of Polysaccharides?

A

Cellulose, starch in plants
Glycogen in animals
Chitin in arthropods

161
Q

Glucaric acid is characterized as what “____________-“

A

water soluble

162
Q

Galactaric acid is characterized as what “____________-“

A

nonpolar due to symmetry (water insoluble).

163
Q

What is the basis of mucic acid test used to differentiate glucose from galactose.

A

polarity and solubility

164
Q

This sugar acid is related to the Oxidation of the aldehyde group of aldoses

A

Aldonic acids

165
Q

This sugar acid is related to the Oxidation of the primary alcohol group of aldoses

A

alduronic acids

166
Q

This sugar acid is related to the Oxidation of both with concentrated HNO3

A

aldaric acid

167
Q

what kind of acid is d-gluconic acid?

A

Aldonic acids

168
Q

What kind of acid is d-glucuronic acid?

A

Alduronic acid

169
Q

What kind of acids are glucaric and Galactaric acid

A

Aldaric acid

170
Q

These are known as sugar alcohols. These are known as sweeteners in chewing gum and accumulates in the lens of diabetics resulting to cataracts

A

Glucitols

171
Q

How can an aldehyde group or keto group be reduced?

A

The aldehyde group or keto group can be reduced to a 1o alcohol or 2o alcohol using H2 as reducing agent.

172
Q

What occur predominantly as a cyclic structures?

A

aldotetroses and all monosaccharides with n ≥ 5

173
Q

How are cyclic hemiacetals and cyclic hemiketals formed?

A

Alcohol groups can react with the aldehydes or ketones (The hydroxyl and either the aldehyde or the ketone of monosaccharides can react intramolecularly to form cyclic hemiacetals and hemiketals)

174
Q

what are intramolecular hemiacetal formation?

A

Sugars with ≥ 5 C mostly exist in their cyclic form (Since C1 becomes a chiral center, there are two new possible stereoisomers that are named a and b)

175
Q

These isomeric forms that differ only in their configuration about the hemiacetal or hemiketal carbon atom. ⇒ a, b anomers

A

Anomers

176
Q

This is the hemiacetal carbon atom or the new chiral C.

A

anomeric carbon

177
Q

How is the anomeric carbon formed?

A

Cyclic sugars have 2 anomeric forms. During cyclization, the carbonyl carbon becomes a chiral center and is called, the anomeric carbon with two possible configurations.

178
Q

How do Disaccharides arise?

A

They arise through the formation of O-glycosidic bonds: condensation of anomeric carbon hydroxyl group with an alcohol.

179
Q

How is lactose formed

A

condensation of a molecule of β-D galactopyranose with a molecule of D-glucose (a or b) through β-I,4- glycosidic linkage.

180
Q

How is sucrose formed?

A

the condensation of a molecule of a-D-glucopyranose with a molecule of β-D-fructofuranose through α-1,2-glycosidic bond

181
Q

What is the monomer and linkage of maltose respectively?

A

Two a-D-GLUCOSE and a-1,4-GLYCOSIDIC

182
Q

What is the monomer and linkage of lactose respectively?

A

B-D GALACTOSE and a-D-GLUCOSE and b-1,4-GLYCOSIDIC

183
Q

What is the monomer and linkage of sucrose respectively?

A

a-D-FRUCTOSE and a-D-GLUCOSE and b-1,2-GLYCOSIDIC

184
Q

What is the monomer and linkage of cellobiose respectively?

A

Two b-D-GLUCOSE and b-1,4-GLYCOSIDIC

185
Q

What is the monomer and linkage of isomaltose respectively?

A

Two a-D-GLUCOSE and a-1,6-GLYCOSIDIC

Biochemistry (16 decks)

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