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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
Aldaric acid
-Oxidation at C1 and C6 -Suffix: -aric acid -Example: Glucaric acid
26
Alditol
-Reduction at C=O -Suffix: -itol -Glucitol
27
Where are the free aldonic acids in equilibrium with?
Lactones e.g. gluconolactone
28
Sugar Phosphates
H of any -OH bonds is replaced with Phospohate (PO4)^-3
29
Amino Sugars
Any OH bonds is replaced with an amino group
30
Glycosides
-Reaction of the anomeric OH group with the -OH of another compound -Produces an O-glycoside (glycosidic bond)
31
Disaccharides
Two monosaccharide unts joined by a glycosidic bond
32
Ways to determine the type of glycosidic bond
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
Maltose composition
Glcα(1->4)Glc
34
Cellubiose Composition
Glcβ(1->4)Glc
35
Lactose Composition
Galβ(1->4)Glc
36
Sucrose
Glcα(1->2)Fruβ
37
Trehalose
Glcα(1->1)Glcα
38
Starch (Amylose)
-Glc joined via α1->4 linkages -Has helical 3D structure
39
Starch (Amylopectin)
-Glc joined via α1->4 and α1->6 linkages -Branches every 12-30 residues
40
Glycogen
-Glc joined via α1->4 and α1->6 linkages -Branches every 8-12 residues (more branches to generate more glucose for energy)
41
Dextrans
-Glc joined via α1->6 linkages
42
Cellulose
-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
Chitin
N-acetylglucosamine acid (GlcNAc) joined via β1->4 linkages
44
α-chitin
Parallel
45
β-chitin
Antiparallel
46
γ-chitin
Pairs of parallel sheets separated by antiparallel sheet
47
Agar(Agarose)
-Alternating Gal and 3,6-anhydro-L-Gal chains with 6-methyl-D-Gal side chains
48
Agar (Agaropectin)
Agarose with negatively charged sulfate or -COOH groups (more polar)
49
Glycosaminoglycans (GAG)
-Repeating disaccharide units -Sugar: N-acetylgalactosamine (GalNAc) or GlcNAc or one of their derivatives. -Contains (SO4)^-2 or -COO-
50
Proteoglycan
-Carbohydrate>protein content -Composed of repeating heteropolysaccharide -Long carbohydrate chain (~50 sugar units) -Linked to protein via Ser -Composed of glycosaminoglycans -Example: Aggrecan
51
Glycoprotein
-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
O-linked Glycans
-Attached via Ser, Thr, Hyl -Sugars: GalNAc
53
N-linked Glycans
-Attached via Asn -Sugars: 2 GlcNAc linked to branched Manose triad
54
O antigen
Universal blood donor -Every antigen contains the same structure as this
55
AB antigen
Universal blood acceptor -All of the components found in other antigens are found in this antigen
56
Sialic Acid
At the termini of oligosaccharidespresent on cell-surface glycoproteins and glycolipids.
57
Hemagglutin
Holds on to sialic acid
58
Neurominidase
Nicks sialic acid
59
Peptidoglycan
Cell wall of bacteria
60
Peptidoglycan Composition
-N-acetylglucosamine (NAG or GlcNac) -N-acetylmuramic acid (NAM)
61
Peptidoglycan Linkages
1. Ala-Glu-Lys-Ala (tetrapeptide) to NAM 2. Gly5 (pentapeptide) to tetrapeptide
62
Glycopeptide transpeptidase
-Catalyzes the reaction that form the cross-linkage -Contains a catalytic Ser residue
63
Glycopeptide transpeptidase mechanism
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
Penicillin
-Suicide inhibitor (irreversible) -Contains a variable R group, β-lactam ring, and thiozolidine
65
Penicillin mechanism
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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