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Biochemistry: Ch 8 & Ch 9 > Ch 8: Carbohydrates > Flashcards

Ch 8: Carbohydrates Flashcards

1
Q

Carbohydrates

A

made up of molecules of C, H, and O

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2
Q

Monosaccharides

A
  • aldehyde or ketone, 3+ carbons, polyhydroxy, alcohols
  • aka “sugar”
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3
Q

Fisher projections

A
  • way of representing the 3D structure in a simplified way
  • horizontal = out of plane of paper
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4
Q

How to find # of stereoisomers of an organic compound?

A
  • 2^n
  • where n= # chiral carbon
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5
Q

By changing the stereochemistry of carbons…

A

…you can make more versions of these molecules

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6
Q

Naming

A
  • by func. group
  • by # C
  • Combined func. group and #C
  • stereochem. of last chiral C
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7
Q

By functional group

A
  • aldehyde = aldose
  • ketone = ketose
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8
Q

By # C

A

SI prefix = “ose”

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9
Q

Stereochemistry of LAST chiral C

A
  • D = OH on right
  • L = OH on left
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10
Q

CH2OH

A

must always be kept at bottom

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11
Q

Epimers

A
  • different configuration around 1 carbon
  • can have multiple
  • the more C you have the more epimers you are going to have
    *ONLY ONE chiral center w/ diff configuration
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12
Q

enantiomers

A
  • all chiral centers have different configuration
  • non superimposable
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13
Q

If you have a diff. in stereochem in more than one chiral carbon…

A

…it is not an epimer

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14
Q

Alcohols react with ?

A

carbonyl groups

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15
Q

Cyclic sugars

A
  • 6-member ring = pyranose
  • 5-member ring = furanose
    (Remove “se” at the end and add pyranose/furanose)
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16
Q

Alcohol + Aldehyde = ?

A

Hemiacetal

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17
Q

Alcohol + Ketone = ?

A

Hemiketal

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18
Q

isomer

A

same formula, diff structure

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19
Q

anomeric carbon

A

carbonyl C of cyclized sugar
- bears the aldehyde OR ketone functional group

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20
Q

alpha: anomeric carbon

A

OH opposite of D/L chiral carbon CH2OH
*OH that is formed from carbonyl C

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21
Q

beta: anomeric carbon

A

Oh same side of D/L of chiral carbon CH2OH
*OH that is formed from carbonyl C

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22
Q

depending on how the cyclized sugar is tied up…

A

makes certain molecules more reactible/digestible in organisms

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23
Q

Fisher Projection —> Haworth Projection

A
  1. draw ring
  2. # clockwise w/ 1 at anomeric carbon
  3. place hydroxyl groups
    - right = down
    - left = up
  4. Place CH2OH
    - D = up
    - L = down
  5. place anomeric - OH
    - Beta = same side
    - Alpha = opposite side
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24
Q

modifications

A

not all carbs will have CHO
- these changes ultimately impact the way these groups will interact w/ their surroundings

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25
Q

Modifications: oxidation

A
  • aldose = aldonic acid
  • primary alc = uronic acid
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26
Q

Modifications: reduction

A

aldose or ketose = alditols

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27
Q

Modifications: replace OH groups

A
  • H = deoxy
  • NH2 = amino sugar
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28
Q

mutarotation

A

conversion b/t alpha and beta configuration of cyclic sugar

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29
Q

glycosidic bonds

A
  • anomeric C condenses w/ alcohol (-C-O-C)
  • reducing sugar
  • nonreducing sugar
30
Q

glycosidic bonds: anomeric C condenses w/ alc

A
  • alpha-glycosidic bond
  • beta-glycosidic bond
    —- named as GreekLetter(C#monosacc—>C3monosacc 2)
    (doesn’t matter conformation, they maintain it while forming bond)
31
Q

glycosidic bonds: reducing sugar

A

free anomeric C (not in glycosidic bond)

32
Q

glycosidic bonds: nonreducing sugar

A

no free anomeric C

33
Q

Disaccharides

A
  • simplest polysaccharide
  • lactose & sucrose
34
Q

Polysaccharide

A

monosaccharides linked by glycosidic bond, also called glycans

35
Q

homopolysaccharide

A

formed from a single type of monosaccharide

36
Q

heteropolysaccharide

A

greater than one monosaccharide

37
Q

oligosaccharide

A

few ( >3, but < 10) monosaccharides linked together

38
Q

exoglycosidases

A

enzymes that hydrolyze monosaccharides at the end of a polysacc. chain

39
Q

endoglycosidases

A

enzymes that hydrolyze the middle of polysacc. chain

40
Q

structural polysaccharide: cellulose

A
  • plant cell walls
  • Beta(1–>4) D-glucose
  • sheets
    —–unique structure, advantageous bc tightly packed = extensive H bonds + Van der Waals
  • water insoluble (due partly to sheets)
  • rlly only give structure to organism it is in
41
Q

structural polysaccharide: Chitin

A
  • exoskeleton of invertebrates
  • Beta(1–>4) N-acetyl–glucosamine
42
Q

cellulose is indigestible to humans

A

bc we don’t have the enzyme to digest B glycosidic bond

43
Q

storage polysaccharides: starch

A
  • glycans
  • reducing sugar (free anomeric C)
  • reduces osmotic pressure
  • digestion
44
Q

starch: glycans

A
  • alpha-amylose = straight Alpha(1–>4) glucose
  • Amylopectin = Alpha(1–>4) glucose w/ Alpha (1–>6) branched
45
Q

starch: digestion

A
  • Amylase (saliva & small intestine)
    —–hydrolyzes Alpha(1–>4), Alpha-glucosidase removes 1 Glu at a time, debranching enzyme hydrolyzes Beta(1–>6) linkages
46
Q

storage polysaccharides: glycogen

A
  • animals
  • structure resembles amylopectin with more branching
  • digestion
47
Q

glycogen: digestion

A

glycogen phosphorylase breaks Alpha(1–>4) from nonreducing ends, glycogen debranching enzyme breaks Alpha(1–>6)

48
Q

Hydrated gels

A
  • contain collagen in a gel-like matrix (made up of glycosaminoglycans)
  • extracellular space in cells
  • rlly soft solid, can take shape of its container
  • can be sulfated (impacts interactions…makes them unique)
49
Q

Hydrated gels: glycosaminoglycans

A

alternating uronic and hexosamine residue, unbranched

50
Q

Hydrated gels: hyaluronic acid

A

shock absorber

51
Q

Pectins

A
  • what is used to make jam & jelly
  • in plants
  • heteogeneous polysacc
52
Q

pectins: heterogeneous polysacc

A
  • Alpha(1–>4) galacturonate with rhamose
  • aggregates, requires Ca+
  • highly hydrated gels
  • absorbs shocks
53
Q

glycoproteins

A
  • proteins covered in sugar
  • proteoglycan
  • enormous
  • polyanionic characteristic
  • highly hydrated gels
54
Q

glycoproteins: proteoglycan

A

covalent and noncovalent aggregations of proteins and glycosaminoglycans in the extracellular matrix

55
Q

Highly hydrated gels contributes?

A
  • contributes to squishiness thru movement of water thru pores
  • absorbs shocks
56
Q

Peptidoglycan

A
  • covalently linked polysaccharide & polypeptide chain
  • bacterial cell walls
57
Q

bacterial cell walls

A

Beta(1–>4) N-acetylglucosamine

58
Q

gram positive bacteria

A

any bacteria that absorbs a chemical called gram stain
- pretty thick

59
Q

gram negative bacteria

A

won’t absorb a chemical called gram stain

60
Q

glycosylated

A
  • proteins w/ oligosaccharides covalently attached
  • N-Linked (Asn - X - Ser or Thr, where X is any amino acid except Pro and rarely Asp)
61
Q

can use polysaccharides to make modifications to?

A

sugars

62
Q

sugar code

A

idea that a lot of proteins are uniquely identified by the cell by the sugars that are attached to the protein surface

63
Q

N-links happen while protein is?

A

being synthesized

64
Q

O-linked Oligosaccharide

A
  • like a glycosidic bond
  • b/t sugar & Ser/Thr (Ser/Thr have a primary alc)
  • synthesized in golgi
  • Ser or Thr residue (no specific sequence required)
65
Q

N-linked: carbs attached to proteins

A
  • through terminal N group of Asn
  • a lot of requirements
  • while protein is being synthesized
66
Q

O-linked: carbs attached to proteins

A
  • can attach to OH of Ser/Thr
  • after protein synthesis
  • not as picky
67
Q

Function of saccharides

A
  • glycoforms
  • define proteins structure
  • mediate recognition events
  • antigenic determinants
  • have a lot more variability & info that we can convey by using saccharides to signal & decorate proteins*
68
Q

Function of saccharides: glycoforms

A
  • same protein w/ variation in sequence, location & number of covalently attached carbohydrates
  • can have a diff type of carb/oligosaccharide
69
Q

Function of saccharides: mediate recognition events

A
  • to allow entry
  • SUGAR CODE
70
Q

Function of saccharides: Antigenic determinants

A
  • immunochemical markers = determined by carbs on it
    “why certain blood types clot & some don’t”

Biochemistry: Ch 8 & Ch 9 (2 decks)

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