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BIOCH 320 > 8-carbohydrates (midterm 2 cutoff) > Flashcards

8-carbohydrates (midterm 2 cutoff) Flashcards

1
Q

what is the general formula of carbohydrates

A

(CH2O)n

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2
Q

what are some other elements that can be found in carbohydrates

A

N S P

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3
Q

what are carbohydrates (definition)

A

polyhydroxy aldehydes or ketones

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4
Q

what are 4 roles of carbohydrates

A
  • fuel source/storage
  • structural compounds
  • recognition/regulation of extracellular proteins
  • nucleic acid structure
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5
Q

are monosaccharides water soluble

A

yes

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6
Q

are disaccharides water soluble

A

yes

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7
Q

are oligosaccharides water soluble

A

yes

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8
Q

are homopolysaccharides water soluble

A

no

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9
Q

are heterpolysaccharides water soluble

A

no

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10
Q

what are homopolysaccharides and heteropolysaccharides

A

polymers of one or more carbohydrate unit, large and insoluble

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11
Q

what are glycoconjugates

A

carbohydrates joined to other molecular classes

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12
Q

what are 4 examples of glycoconjugates

A

proteoglycans, glycoproteins, peptidoglycan, glycolipids

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13
Q

what is a monosaccharide

A

aldehyde or ketone with two or more hydroxyl groups

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14
Q

what kind of chain is in monosaccharides and how are they connected

A

ubranched chains connected by single bonds

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15
Q

what is the chirality of monosaccharides

A

multiple chiral carbons

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16
Q

what is an aldose

A

when C1 has a carbonyl

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17
Q

what is a ketose

A

when C2 has a carbonyl

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18
Q

how do you name monosaccharides

A

based on the number of carbon atoms

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19
Q

what does triose mean

A

3 Carbon atoms in the monosaccharide

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20
Q

what does hexose mean

A

6 Carbon atoms in the monosaccharide

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21
Q

what is those most common # of C in monosaccharides

A

hexose 6

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22
Q

where does numbering begin in monosaccharides

A

the carbon closest to the carbonyl

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23
Q

why is glucose called an aldohexose

A

it has double bond at c1 and 6 carbons

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24
Q

how many chiral centers do all monosaccharides (except for dihydroxyacetone) have

A

at least 1

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25
Q

For N chiral centers, how mant possible steroisomers are there

A

2^N

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26
Q

what are epimers

A

isomers that differ in configuration at one ONE chiral carbon

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27
Q

what classified monosaccharides as D or L

A

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

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28
Q

what are enantiomers

A

mirror reflection stereoisomers

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29
Q

in fishcer projection, whcih side will the OH be on (starting from the C furthest from the carbonyl) for it to be a D isomer

A

OH on the right

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30
Q

in fishcer projection, whcih side will the OH be on (starting from the C furthest from the carbonyl) for it to be a L isomer

A

OH on the left

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31
Q

which carbon on glucose determines whether its D or L

A

C5

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32
Q

what happens if there is more than 2 chiral centers adjusted in a molecule (so if you compare the OG molecule to the one with 2 changed chiral centers)

A

it is not an epimer or an enantiomer - its just a stereoisomer

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33
Q

how many epimers of D-glucose are also D monosaccharides

A

3 (you can change C2 C3 and C4)

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34
Q

with an aldose and ketose with the same amount of carbons, how do they compare with the amount of chiral centers

why

A

there is 1 less chiral center in the ketoses compared to the aldose equivalents (because the ketone at C2 removes one stereocenter)

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35
Q

what is a pyranose

A

6 membered ring

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36
Q

what is a furanose

A

5 membered ring

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37
Q

what is the carbonyl converted to when it becomes a cyclic structure

A

either hemiacetal (aldose) or hemiketal (ketose)

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38
Q

how do monosaccharides adopt cyclic conformation (what is the reaction)

A

intramolecular rxn, C5 OH groups acts as a nucleophile towards the C1 or C2 carbonyl

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39
Q

what is an anomeric carbon

A

the carbon that is now in chiral form due to the monosaccharide becoming cyclic (so either C1 in aldoses or C2 in ketoses)

40
Q

what is the structure of a hemiacetal

A

when an alcohol and ether are attached to the same carbon

41
Q

what is the structure of a hemiketal

A

alcohol and ether attached to the same carbon with 2 other carbons attached

42
Q

what is the difference with a hemiketal and a hemiacetal

A

hemiacetal will have an extra H group, in hemiketal that H group would be a C

43
Q

how does the cyclic and linear form compare with the amount of chiral centers

A

the cyclic has 1 more chiral center

44
Q

what 2 molecules react to create the hemiacetal

A

C-5 hydroxyl reacts with C-1 aldehyde

45
Q

which is the anomeric carbon in glucose

A

C1

46
Q

which is the new chiral carbon in glucose

A

C1

47
Q

when do you have alpha glucose

A

then the OH of C1 is on the opposite side of the ring relative to C6 (OH down), C6 up)

48
Q

when do you have beta glucose

A

then the OH of C1 is on the same side of the ring relative to C6 (OH up, C6 up)

49
Q

how can you interconvert alpha and beta forms

A

by reforming the hemiacetal (mutarotation)

50
Q

how do you know if glucose in ring structure is L

A

C6 will be down

51
Q

how do you know if glucose in ring structure is D

A

C6 will be up

52
Q

where is C6 and OH in alpha-D-glucopyranose

A 
C6 up (D)
OH down (alpha)
53
Q

where is C6 and OH in beta-D-glucopyranose

A 
C6 up (D)
OH up (beta, same side)
54
Q

where is C6 and OH in alpha-L-glucopyranose

A 
C6 down (L)
OH up (alpha means opposite site)
55
Q

which OH carbon determines whether its alpha or beta

A

the OH on C1

56
Q

where is C6 and OH in beta-L-glucopyranose

A 
C6 down (L)
OH down (beta, same side)
57
Q

which form of glucopyranose has C6 up OH down

A

alpha-D-glucopyranose

58
Q

which form of glucopyranose has C6 down OH down

A

beta-L-glucopyranose

59
Q

which form of glucopyranose has C6 up OH up

A

beta-D-glucopyranose

60
Q

which form of glucopyranose has C6 down OH up

A

alpha-L-glucopyranose

61
Q

what % is usually beta in glucopyranose (how much is in that form compared to to other forms)

A

66%

62
Q

what % is usually alpha in glucopyranose (how much is in that form compared to to other forms)

A

33%

63
Q

what % is usually linear in glucopyranose (how much is in that form compared to to other forms)

A

less than 1%

64
Q

is interconversion between alpha and beta spontaneous

explain (2 things)

A

yes, it will slowly come to equilibrium with the linear form as an intermediate

65
Q

what is the name of the cyclic 5 carbon monosaccharide

A

furanose

66
Q

what is the name of the cyclic 6 carbon monosaccharide

A

pyranose

67
Q

which cyclic form can aldoses with 5 or more carbons form

A

pyranose or furanose

68
Q

is pyranose or furanose more stable and why

A

pyranose because its larger

69
Q

if OH is down on the Haworth projection, will it be on the right or left side in a fischer projection

A

right

70
Q

whats the best 2 step process to determine whether its beta/alpha and L/D

A

1- look at C6 (down=L up=D)

2-look at C1 (opposite to C6=alpha same as C6=beta)

71
Q

if OH is up on the Haworth projection, will it be on the right or left side in a fischer projection

A

left

72
Q

if found on the left of the fischer diagram, will the OH be on the top of bottom in Hayworth

A

top

73
Q

if found on the right of the fischer diagram, will the OH be on the top of bottom in Hayworth

A

down

74
Q

what is so special about the bonding patten in anomeric carbons

A

they are the only ones that are attached to 2 oxygens (OH and ether)

75
Q

is bond breaking required to go between chair conformations of pyranose rings

A

no

76
Q

is it most stable to have equatorial or axial position in the chair

A

equitorial

77
Q

thinking about the cyclohexane chair model, why is the beta form more common than alpha

A

because alpha requires you to have some the OH and C6 pointing in opposite directions, so there will be at least 1 thing in the axial form (but beta can have all in equitorial which is more stable)

78
Q

where does the ether come from in glucopyranose

A

the OH from C5

79
Q

what attacks which carbon to make a furanose ring

A

OH from C5 attacks carbonyl from C2

80
Q

what attacks which carbon to make a pyranose ring

A

OH from C5 attacks carbonyl from C1

81
Q

what are aldonic acids

A

oxidation at C1

82
Q

how do you name aldonic acids

A

“-onic acid”

83
Q

what are uronic acids

A

oxidation of primary alcohol

84
Q

how do you name uronic acids

A

“-uronic acid”

85
Q

what are 2 types of oxidized sugars

A

aldonic and uronic acids

86
Q

what is a type of reduced sugar

A

alditol

87
Q

what is an alditol

A

reduction of carbonyl to alcohol

88
Q

how do you name alditols

A

“-itol”

89
Q

what are deoxy sugars

A

removal of OH from monosaccharide

90
Q

what is an amino sugar

A

replacement of OH (usually at C2) in monosaccharide with NH2 / NH3+

91
Q

how do you name aino sugars

A

“-amine”

92
Q

how and where do amino sugars differ than a normal sugar

A

OH is replaced with NH2 NH3+ (usually at C2)

93
Q

what often happens to the amino group in amino sugars

A

it is acetylated

94
Q

is there a charge on acetylated amino sugars

A

no

95
Q

is there a charge on amino sugars

A

yes

BIOCH 320 (16 decks)

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