Chapter 7 Flashcards

1
Q

what are the 7 physiological functions of carbohydrates

A

1) source of energy
2) energy storage
3) structural roles
4) cellular interaction
5) cellular identification
6) information transfer (DNA and RNA)
7) signalling

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2
Q

what does carbohydrates mean

A

hydrate of carbon

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3
Q

what are the empirical formulas of carbohydrates

A

(CH2O)n where n is greater then or = to 3 (usually 3-6)

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4
Q

what are the two major classes of carbohydrates

A

-aldose (which have aldehyde group)
-ketoses (which have ketone group)

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5
Q

most monosaccharides have multiple…

A

asymmetric carbons

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6
Q

what designates a D or L sugar configuration

A

based on the configuration of the chiral carbon most distant from the carbonyl oxygen

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7
Q

what is the reference molecule for designation of D or L

A

D-glyceraldehyde

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8
Q

what group do all carbohydrates have

A

a carbonyl

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9
Q

what is contained in a ketone and a aldehyde

A

ketone is just a C double bond O and a aldehyde is a C double bond O and a H

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10
Q

what is the L and D configuration based on

A

the configuration of the chiral carbon most distant from the carbonyl oxygen

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11
Q

what side does the OH have to be on to be a D configuration

A

the right side

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12
Q

what side does the OH have to be on to be a L configuration

A

the left side

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13
Q

molecules with n chiral centers will have ____ sterioisomers

A

2^n

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14
Q

what are epimers

A

sugars that differ in configuration at one and only one chiral carbon

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15
Q

draw out a D-ribose

A
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16
Q

draw out a D-deoxyribose

A
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17
Q

draw out a D-glucose

A
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18
Q

draw out a D-mannose

A
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19
Q

draw out a D-galactose

A
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20
Q

draw out a D-fructose

A
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21
Q

draw out a dihydroxyacetone

A
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22
Q

draw out a D-glyceraldehyde

A
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23
Q

what has more chiral Cs aldose or ketosis

A

aldose has one more chiral C

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24
Q

what do longer carbohydrates tend to do in solution

A

longer carbohydrates (5 Cs and more) tend to be cyclized

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25
Q

what is longer C cyclized structures the result of

A

formation is the result of a reaction of an internal alcohol (hydroxyl group) with either:
1) an aldehyde (aldose) to form a hemiacital
2) a ketone (ketoses) to form a hemiketal

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26
Q

what is a stereoisomer

A

atoms are connected in the same order but differ in spatial arrangement

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27
Q

what is a epimer

A

they differ at one of several asymmetric carbon atoms

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28
Q

what is a isomer

A

they have the same molecular formula but different structures

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29
Q

what are constitutional isomers

A

they differ in the order of attachment of atoms

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30
Q

what is a enantomer

A

non superimposible mirror images

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31
Q

what are diastereoisomers

A

isomers that are not mirror images

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32
Q

what is anomers

A

isomers that differ at a new asymmetric carbon atom formed on ring closure

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33
Q

are all anomers epimers?

A

yes

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34
Q

are all epimers anomers?

A

no

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35
Q

what does cyclization of glucose involve

A

the C5 hydroxyl and the C1 aldehyde

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36
Q

in cyclization what happens when a C1 chiral is rendered

A

it produces two stereoisomers a and B

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37
Q

what is a anomeric carbon

A

the carbon that becomes chiral as a result of cyclization

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38
Q

what are the a and B forms of cyclization of eachother

A

they are a and B forms of each other

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39
Q

how can you tell if a carbohydrate molecule is a or B

A

you look at the carbon 1
if the OH is above the plane of the sugar its B
if the OH is below the plane of the sugar its a

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40
Q

cyclization produces a new ____ at the ____ resulting in two _____

A

chiral carbon, anomeric carbon, new stereoisomers (a and B)

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41
Q

what happen to a and B configurations in solution

A

they interconvert by a process called mutarotation

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42
Q

what is mutarotations intermedeate

A

it does from cyclization to linear intermediate back to cyclization

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43
Q

what does mutarotations represent

A

a change in configuration

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44
Q

what conformation fraction does glucose tend to be in solution

A

2/3 B-glucopyranose
1/3 a-glucopyranose
and less then 1% linear

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45
Q

what does the cyclization of fructose involve and what does it render

A

it involves the C5 hydroxyl and the C2 ketone
it renders C2 chiral (anomeric carbon) producing a and B sterioisomers

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46
Q

what ring does fructose exist in

A

both pyran and furan

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47
Q

where is B-fructopyranose found

A

in honey and its extreamly sweet

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48
Q

what happens when you heat B-fructopyranose

A

it promotes its conversion to B-fructofuranose (which is less sweet)

49
Q

why is corn starch which contains lots B-fructopyranose used to sweeten

A

cold but not hot drinks because it would go to its less sweet form B-fructofuranose

50
Q

what doe carbohydrates derivatives do to the glucose formula

A

it breaks from the empirical formula

51
Q

what things can sugar derivatives contain

A

they can include nitrogen, phosphate, and sulphur groups

52
Q

what things do sugar derivataves indicate

A

they usually indicate specialized functions
i.g muscle lubrication

53
Q

what is myrosinase and glucosinolate

A

-found in plants as a survival defence
-myronose is an enzyme
-they are produces and stored separately but come together upon tissue damage
-when they come together they produce glucose and isothiocyanate (has a sharp, bitter taste)
-discourages herbivores from eating

54
Q

what does myrosinase and glucosinolate come together to create

A

glucose and isothiocyanate

55
Q

what can oxidize linear forms of monosaccharides

A

mild oxidizing agents like iron and copper

56
Q

what happens when linear forms of monosaccarides are oxidized

A

the carbonyl group os oxidized into a carboxyl group

57
Q

what does oxidizing linear forms of monosaccharides allow us to do

A

-allows for the quantifications of sugars present in blood or urine
-also defines the end of the sugar with the carbonyl carbon as being the reducing end

58
Q

what are glycosidic bonds and what are the different ones

A

-primary structural linkage in all polymers of monosaccharides
-O-glycosidic bonds occur through oxidation
-N-glucosidic bonds occur through nitrogen

59
Q

what things does the nomenclature of disaccharides specify

A

-the monosaccharides involved in the disaccharide
-their ring types (puran, furan)
-their configurationd (alpha or beta)
-their linkages (C1-C4 etc…)
-the end of the chain with a free anomeric carbon called the reducing end of the polymer

60
Q

the end of the chain with a free anomeric carbon is called…

A

the reducing end of the polymer

61
Q

monosaccharides have multiple hydroxyl groups what does this mean

A

there are many different glycolic linkages possible

62
Q

how many different structures could just 3 monosaccharides create? (glucose, galacose and mannose)

A

12000 different stuctures

63
Q

what are higher order carbohydrate structures in (disaccharides) generated through

A

-the action of glycosyltransferases
-glycosyltransferases uses monosaccharides that are activated through linkage with UPD

64
Q

how do you use nomenclature to distinguish the configuration of cyclic carbohydrates

A

identify if its alpha or beta at the anomeric carbon

65
Q

what nomenclature would you use to specify ring form of cyclic carbohydrates

A

furan or pyran

66
Q

how would you use nomenclature to indicate reducing sugars or nonreducing sugars

A

non reducing has the suffix osyl
reducing sugar has the suffix ose

67
Q

how do you use nomencature to determine how the disaccharides are bonded togeter

A

indicate in parentheses the two different carbon atoms joined by the glycosidic bond with an arrow

68
Q

what are the two steps the prof gave to thing about when naming disaccharides

A

1) look at carbon 1 and see if its alpha or beta
2) look at carbon 4 and see if its glucose or galactose

69
Q

what do lactose intolerant people lack

A

they have insufficent levels of the enzyme (lactase) that catalyses the hydrolysis into a glucose and galactose

70
Q

what happens if lactose intolerant people consume dairy

A

it can lead to bloating, diarrhea, bloating, cramps, nausea

71
Q

are mammals suposed to be able to drink milk

A

mammals cease to produce lactase after weaning but some human populations developed lactase persistence

72
Q

what are some biological functions of polysaccharides

A

energy storage, structural roles and specialized roles such as cushioning and lubrication etc

73
Q

what are homopolysaccharides

A

polymers contining A single type of monosaccharide

74
Q

what are heteropolysaccarides

A

polymer containing more than one type of monosaccharide

75
Q

what is branched hetero or homopolysaccharides

A

both of them can be unbranched or branched

76
Q

what are energy storage polysaccharides

A

starch and glycogen (both homopolysaccharides)

77
Q

what are structural polysaccharides

A

cellulose
chitin
dextran
(homo)
peptidoglycan
agarose
(hetero)

78
Q

what is a specialized structural polysaccharides

A

hyluronate (hetero)

79
Q

where and how is glucose stored in plants and animals

A

glucose is stored intracellularly in polymeric forms in both plants (starch) snd animals (glycogen)
both starch and glycogen are heavily hydrated structures

80
Q

what is starch and where is it found

A

it is a mixture of two molecules, amylose (unbranched) and amylopectin (branched)
its found in plants and fungi

81
Q

where is glycogen found

A

its stored in the liver and skeletal muscles of animals

82
Q

is glycogen a long term energy storage

A

-you have about 24 hours of storage
-its not a very long term storage due to its polarity
-it can also be used in the case of extreme exersize hence why its also found in muscle

83
Q

what is amylose and amylopectin

A

amylose: its a linear polymer of glucose residues through alpha(1-4) bonds

amylopectin: consists of alpha(1-4) linked glucose residues with alpha(1-6) branch points every 24-30 residues (on average)

84
Q

what cuts the amylose and amylopectin branches

A

alpha(1-4) is cut by amylase
alpha(1-6) branche points by debranching enzymes

85
Q

branches create more…

A

non reducing ends

86
Q

the more reducing ends you have the faster you can…

A

mobilize your energy storage

87
Q

how do amylose and amylopectin compare interms of reducing and non reducing ends

A

both have a single reducing ends
amylose has a single non-reducing end
amylopectin has multiple non reducing ends

88
Q

where is glycogen found

A

in all cells but most prevalent in skeletal muscles and liver

89
Q

what is glycogen like structrally

A

its structrally identical to amylopectin and consists of alpha (1-4) linked glucose residues with alpha(1-6) branch points but with a higher frequency of branch points (every 10 residues)

90
Q

when and how is glycogen mobilized

A

its mobilized in times of need by glycogen phosphoralase which sequential cleaves glucose residues from non reducing ends

91
Q

in polysaccharides greater frequency is branching allows for…

A

rapid mobilization

92
Q

why is rapid mobilization of energy storage beneficial in humans and not plants

A

because for use being able to access that energy helps us to fight or run faster which determines our survival. plants dont use this as survival mechanism.

93
Q

for humans the more densely branched structure =…

A

faster access to our energy

94
Q

what is the primary component of plant walls

A

cellulose (fiber)

95
Q

how much of the carbon in the biosphere does cellulose account for

A

over half

96
Q

how is cellulose made up

A

its linear, homopolysaccaride of glucose residues
and has a linear arrangement of beta(1-4) glycosidic residues

97
Q

can amylase break down cellulose

A

no it cannot cut the beta(1-4) glycosidic residues

98
Q

where do we see the use of chitin

A

as the principal component of hard exoskeletons (insects, lobsters, etc)

99
Q

how is chitin made up

A

its a linear, homopolysaccharide of N-acetalglucosamine residues

100
Q

what is the chemical difference between cellulose and chitin

A

the replacement of hydroxyl group at C2 with acetylates amino groups

101
Q

what does the beta linkages of cellulose and chitin allow for

A

the formation of long straight chains called fibrils this fiber generates a digid supportive structure of high tensile strangth

102
Q

how are fibrils formed

A

by parallel chains that are linked through hydrogen bonds

103
Q

what structure does the alpha(1-4) linkages of starch and glycogen form. and what does these structures do

A

they form hollow, helical structures
the hollow helix provides a compact, accessible storage structure of glucose

104
Q

what are glycolipids

A

sugars can also be covalently linked to lipid molecules to form glycolipids

105
Q

what is a central function of glycolipids

A

is in the blood groups antigens

106
Q

how does the body use glycolipids in blood to help determine if its itself or not

A

different patterns of sugars presented on the surface of cells by the glycolipids help the body to discriminate self from non self

107
Q

what enzyme have scientist created to make blood tranfusions easier

A

an enzyme that snips off the sugars found in type A and B blood, making it more like type O

108
Q

what are glycoproteins

A

-proteins with covalently attached sugars
-the protein constituent is the largest component by weight
-serves in a variety of biological roles

109
Q

what are proteoglycans

A

-protein component is linked to a particular type of carbohydrate called a glycosaminoglycan
-the carbohydrate constituent is the largest component by weight
-often serves structural and lubricating functions

110
Q

what post translational mods do proteins undergo to become glycoproteins

A

post-translational glycosylation (additions of sugar groups)

111
Q

how many proteins are modified with sugar groups

A

almost half biological proteins

112
Q

what does post translational glycosylation regulate

A

-modifications regulate the structure and function of the protein

113
Q

what does post translational glycosylation involve when it comes to sugar attachment

A

-modifications often involve complex, specific patterns of sugar attachment
-sugars are attached to either:
the amide nitrogen of the side chain of an asparagine (N-linked)
the hydroxyl oxygen of the side chain of serine or threonine (O-linked)

114
Q

what is erythropoietin (EPO)

A

-it simulates red blood cell production
-its highly effective in the treatment of anaemia
-has three N-liked and O-linked glycosylations
-its also exploited by the endurance athletes to increase oxygen carrying capacity
-the patterns of glycosylation associated with the synthetic version of EPO differ from those of the endogenous proteins

115
Q

how many membered rings are pyranose and furansose

A

pyran is a 6 membered sugar ring
furan is a 5 membered ring

116
Q

how do you calculate the number os stereoisomers in a carbohydrate

A

First determine the number of chiral carbons then follow the formula 2n where n is the number of chiral carbons. If n =1 there are 2 stereoisomers, n=2 there are 4 stereoisomers, n= 3 there are 8 stereoisomers and n =4 there are 16 stereoisomes.

117
Q

what molecule are the designation of D and L relative to the reference of

A

D-glyceraldehyde

118
Q

what designates a D or L sugar configuration

A

based on the configuration of the chiral carbon most distant from the carbonyl oxygen