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MMBiochem > Carbohydrate structure and function > Flashcards

Carbohydrate structure and function Flashcards

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1
Q

Basic unit of carbohydrates

A

Monosaccharides

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2
Q

Suffix for carbohydrates with 3 carbon chain

A

Triose

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3
Q

3 carbon carbohydrate with an aldehyde

A

Aldotriose

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4
Q

3 carbon carbohydrate with a ketone

A

Ketotriose

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5
Q

Which carbon is able to participate in glycosidic linkages?

A

Aldehyde carbon

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6
Q

Purpose of glycosidic linkages

A

Allow sugars to act as substituents

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7
Q

All carbons, except the aldehyde or ketone, have what functional groups in a carbohydrate?

A

-OH or hydroxyl groups

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8
Q

D-fructose

A 
CH2OH
             |
            C=O
             |
OH-----C------H
             |
H--------C-----OH
             |
H--------C-----OH
             |
            CH2OH
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9
Q

D-glucose

A 
CHO
             |
    H-----C------OH
             |
 HO-----C-----H
             |
H--------C-----OH
             |
H--------C-----OH
             |
            CH2OH
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10
Q

D-galactose

A 
CHO
             |
    H-----C------OH
             |
 HO-----C-----H
             |
HO-----C-----H
             |
H--------C-----OH
             |
            CH2OH
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11
Q

D-mannose

A 
CHO
             |
 HO-----C-----H
             |
HO-----C-----H
             |
H--------C-----OH
            |
   H-----C------OH
            |
            CH2OH
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12
Q

Optical Isomer/Stereoisomers

A

Same chemical formula but differ in spatial arrangements

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13
Q

Enantiomers

A

Stereoisomers that are nonidentical nonsuperimposable mirror images of each other. They have no internal plane of symmetry.
Same sugars in different optical families

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14
Q

Absolute configurations

A

D or L

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15
Q

Number of stereoisomers

A

2^n where n is number of chiral carbons

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16
Q

(+) rotation

A

Rotate light to right

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17
Q

(-) rotation

A

Rotate light to left

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18
Q

Fischer projection line meanings

A

Horizontal lines are coming out of page towards you and vertical lines are into page or away from you

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19
Q

How to determine D or L?

A

The placement of -OH on the highest number carbon determines D (right) or L (left)

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20
Q

Diastereomers

A

2 sugars that are both aldoses or ketoses and have the same # carbons but not identical and not mirror images

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21
Q

Epimers

A

Diastereomers differing at only one chiral center

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22
Q

Hydroxyl group

A

Nucelophile

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23
Q

Carbonyl

A

Electrophile

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24
Q

Cyclic hemiacetals form from

A

aldoses

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25
Cyclic hemiketals form from
Ketoses
26
Pyranose
6-membered rings
27
Furanose
5-member rings
28
Anomeric carbon
Carbonyl carbon becomes chiral in cyclic form
29
α-anomer
-OH and -CH2OH are trans to each other
30
β-anomer
-OH and -CH2OH are cis to each other
31
Furanose adopt which shape
Planar
32
Pyranose adopt which shape
Chair configurations
33
Fischer to Hawthorn
Groups on right point down
34
Mutorotation
In water, hemiacetals switch between open and closed. The single bond between C1 and C2 can rotate and so either α-anomer or β-anomer can be formed. Mutorotation happens quickly if acid/base added.
35
In solution, which anomer is favored and why?
β-anomer is more favored because α-anomer has more steric strain.
36
Oxidation of carbohydrates yields
energy
37
Aldehyde is oxidized to
Carboxylic acids
38
Aldonic acids
Oxidized aldoses
39
Aldoses are (reducing/oxidizing) agents
Reducing since they are oxidized
40
Reducing sugar
Hemiacetal ring monosaccharide
41
Lactone
Oxidized aldose in ring form; cyclic ester with C=O on anomeric carbon
42
Tollen's reagent
- Detects reducing sugars | - This reagent reduces to make silver mirror solution when aldoses are present
43
Benedict's reagent
- Detects reducing sugars | - Oxidizes aldehyde groups and makes red precipitate
44
Can ketose sugars be reducing sugars as well?
Yes. They tautomerize (rearrange bonds) to make an enol
45
Enol
Double bond and -OH group
46
Under what conditions can reducing ketoses make aldoses?
Basic conditions
47
Alditol
Aldose reduced to alcohol
48
Deoxy sugar
Hydrogen replaces hydroxyl group
49
Esterification
-OH groups can react with carboxylic acid or derivatives to make esters
50
Phosphyrylation
``` Is similar to esterification and makes phosphate ester O || R-O-P-O** | O** ```
51
Reagent to turn hemiacetal into acetal
Alcohol
52
Reagent to turn -OH group into ester
ROH
53
Glycosides
Formed acetals
54
Bonds in polysacharrides
Glycosidic bonds
55
Furanosides
Furanose rings as glycosides
56
Pyranosides
Pyranose rings as glycosides
57
Specificity of alpha or beta glycosidic linkages is
nonspecific because anomeric carbon can react with any -OH on second monosaccharide
58
Sucrose (need to know picture and name)
.
59
Lactose(need to know picture and name)
.
60
Maltose (need to know picture and name)
.
61
Polysacharrides
Long chains of glycosidic linked monosaccharides
62
Homopolysaccharides
Entirely composed of one monosaccharide
63
Heteropolysacharides
Polymer made up of more than one type of monosacharide
64
3 polysacharrides made up of D-glucose
Cellulose, strach, glycogen
65
Branching
When a monosacharide makes 2 glycosidic bonds
66
Cellulose
- In plants - Humans cannot hydrolyze and digest it - It draws water into gut (fiber source)
67
Starches
- More digestible | - Can detect with iodine
68
Amylose
Starch that is linear
69
Amylopectin
Starch that is branched
70
β-amylase
cleaves at end with acetal
71
α-amylase
Cleaves randomly and makes shorter polysacharides
72
Glycogen
Carbohydrate storage unit in animals - highly branched to maximize energy efficiency and enzymes can cleave from many sites - more soluble in solution
73
Glycogen phosphorylase
Cleaves glucose at non reducing end and phosphyrylating it to make glucose-1-phosphate
74
Anomers
Epimers that differ at anomeric carbon

MMBiochem (3 decks)

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