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Biochemistry > Lesson 8: Carbohydrates > Flashcards

Lesson 8: Carbohydrates Flashcards

1
Q

Carbohydrates

A

“Hydrates of carbon”

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2
Q

Functions of carbohydrates

A

-Source of energy and short-term energy reserve (glycogen)
-Supply of C atoms for synthesis of other biomolecules (Proteins, lipids, and nucleic acids)

-Structural framework for DNA and RNA molecules
-Structural components of cell membranes when linked to lipids

-Cell-cell and cell-molecule recognition process when linked to proteins

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3
Q

Characteristics of Monosaccharides

A

-Simple sugars
-Derivatives with 3-9 carbon atoms (small)
-General formula (CH2O)n

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4
Q

Types of monosaccharides

A

Aldose
Ketose

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5
Q

Aldose

A

Polyhydroxyaldehyde
-Bunch of OHs+CH2OH+Aldehyde
-Hemiacetal Haworth Transformation
-Anomeric Carbon at #1

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6
Q

Ketose

A

Polyhydroxyketone
-Bunch of OHs+CH2OH+Ketone
-Hemiketal Haworth Transformation
-Anomeric Carbon at #2

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7
Q

Isomers

A

Same molecules but different structures

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8
Q

Constitutional Isomers

A

Differ in order of attachment of atoms

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9
Q

Stereoisomers

A

Same order of attachment different spatial arrangement

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10
Q

Enantiomers

A

Non-superimposable mirror images

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11
Q

Diastereoisomers

A

Not mirror images (more than 1 connection is flipped but not all)

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12
Q

Epimers

A

Differ at one chiral carbon

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13
Q

Anomers

A

Differ at anomeric carbon (alpha or beta)

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14
Q

Formula to determine number of possible stereoisomer structures

A

2^n (n= number of chiral carbons)

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15
Q

Haworth Projections

A

-Five or six-membered structures of monosaccharides

-Involve hemiacetal/hemiketal formation (alcohol+aldehyde and alcohol+ketone)

-Anomeric carbon: Formation of new chiral carbon

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16
Q

Furanose

A

Haworth projections with 1O+4C

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17
Q

Pyranose

A

Haworth projection with 1O+5C

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18
Q

Conversion from Fischer to Haworth Projection (D-sugars)

A
  1. Anomeric C: Draw on the right
  2. -OH left: -OH up
  3. -OH right- -OH down
  4. Terminal -CH2OH: -CH2OH up
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19
Q

Mutarotation

A

Interconversion between the anomeric forms
-Change of optical rotation between alpha and beta anomers when dissolved in an aqueous solution

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20
Q

Two conversions of the pyranose ring

A
  1. Chair
  2. Boat
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21
Q

Two conformations of the furanose ring

A
  1. C2 endo
  2. C3 endo
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22
Q

Reducing Sugars

A

Carbohydrates that have free anomeric C (capable of being oxidized)

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23
Q

Aldonic acid

A

-Oxidation at C1
-Suffix: -onic acid
-Example: Gluconic acid

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24
Q

Uronic Acid

A

-Oxidation at C6
-Suffix: -uronic acid
-Example: Glucuronic acid

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25
Q

Aldaric acid

A

-Oxidation at C1 and C6
-Suffix: -aric acid
-Example: Glucaric acid

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26
Q

Alditol

A

-Reduction at C=O
-Suffix: -itol
-Glucitol

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27
Q

Where are the free aldonic acids in equilibrium with?

A

Lactones e.g. gluconolactone

28
Q

Sugar Phosphates

A

H of any -OH bonds is replaced with Phospohate (PO4)^-3

29
Q

Amino Sugars

A

Any OH bonds is replaced with an amino group

30
Q

Glycosides

A

-Reaction of the anomeric OH group with the -OH of another compound

    -Produces an O-glycoside (glycosidic 
      bond)
31
Q

Disaccharides

A

Two monosaccharide unts joined by a glycosidic bond

32
Q

Ways to determine the type of glycosidic bond

A
  1. FInd glycosidic bond
  2. Determine carbon #s involved in the bond.
    3.Determine if the anomeric carbon involved is an alpha or beta.
33
Q

Maltose composition

A

Glcα(1->4)Glc

34
Q

Cellubiose Composition

A

Glcβ(1->4)Glc

35
Q

Lactose Composition

A

Galβ(1->4)Glc

36
Q

Sucrose

A

Glcα(1->2)Fruβ

37
Q

Trehalose

A

Glcα(1->1)Glcα

38
Q

Starch (Amylose)

A

-Glc joined via α1->4 linkages
-Has helical 3D structure

39
Q

Starch (Amylopectin)

A

-Glc joined via α1->4 and α1->6 linkages
-Branches every 12-30 residues

40
Q

Glycogen

A

-Glc joined via α1->4 and α1->6 linkages
-Branches every 8-12 residues (more branches to generate more glucose for energy)

41
Q

Dextrans

A

-Glc joined via α1->6 linkages

42
Q

Cellulose

A

-Plant cell wall
-Glc joined via β1->4
-Planar
-Parallel arrangement (all reducing ends on one end)
-Has H-bonding, Higher forces of attraction, More stacked, More compact structure

43
Q

Chitin

A

N-acetylglucosamine acid (GlcNAc) joined via β1->4 linkages

44
Q

α-chitin

A

Parallel

45
Q

β-chitin

A

Antiparallel

46
Q

γ-chitin

A

Pairs of parallel sheets separated by antiparallel sheet

47
Q

Agar(Agarose)

A

-Alternating Gal and 3,6-anhydro-L-Gal chains with 6-methyl-D-Gal side chains

48
Q

Agar (Agaropectin)

A

Agarose with negatively charged sulfate or -COOH groups (more polar)

49
Q

Glycosaminoglycans (GAG)

A

-Repeating disaccharide units
-Sugar: N-acetylgalactosamine (GalNAc) or GlcNAc or one of their derivatives.
-Contains (SO4)^-2 or -COO-

50
Q

Proteoglycan

A

-Carbohydrate>protein content
-Composed of repeating heteropolysaccharide
-Long carbohydrate chain (~50 sugar units)
-Linked to protein via Ser
-Composed of glycosaminoglycans
-Example: Aggrecan

51
Q

Glycoprotein

A

-Protein>carbohydrate content
-Composed of varying monosaccharide units (no monomers)
-Short carbohydrate chain (~3-10 sugar units)
-Linked to protein via Ser, Thr, Hyl, Asn
-Example: ABO blood antigens

52
Q

O-linked Glycans

A

-Attached via Ser, Thr, Hyl
-Sugars: GalNAc

53
Q

N-linked Glycans

A

-Attached via Asn
-Sugars: 2 GlcNAc linked to branched Manose triad

54
Q

O antigen

A

Universal blood donor
-Every antigen contains the same structure as this

55
Q

AB antigen

A

Universal blood acceptor
-All of the components found in other antigens are found in this antigen

56
Q

Sialic Acid

A

At the termini of oligosaccharidespresent on cell-surface glycoproteins and glycolipids.

57
Q

Hemagglutin

A

Holds on to sialic acid

58
Q

Neurominidase

A

Nicks sialic acid

59
Q

Peptidoglycan

A

Cell wall of bacteria

60
Q

Peptidoglycan Composition

A

-N-acetylglucosamine (NAG or GlcNac)
-N-acetylmuramic acid (NAM)

61
Q

Peptidoglycan Linkages

A
  1. Ala-Glu-Lys-Ala (tetrapeptide) to NAM
  2. Gly5 (pentapeptide) to tetrapeptide
62
Q

Glycopeptide transpeptidase

A

-Catalyzes the reaction that form the cross-linkage
-Contains a catalytic Ser residue

63
Q

Glycopeptide transpeptidase mechanism

A
  1. Ser covalently bonds to carbonyl of protein
  2. Break peptide bond
    3.Gly5 forms crosslinkage with carbonyl, break bonds between carbonyl and enzyme
64
Q

Penicillin

A

-Suicide inhibitor (irreversible)
-Contains a variable R group, β-lactam ring, and thiozolidine

65
Q

Penicillin mechanism

A
  1. O of OH attacks the amide bond from β-lactam ring (reactive)
  2. Breaks C-N bond between lactam ring and thiozolidine.
  3. Stable form, no more peptidoglycan

Biochemistry (6 decks)

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