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Med Chem > Biochem 8-9 > Flashcards

Biochem 8-9 Flashcards

(61 cards)

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1
Q

Carbohydrate applications

A

-energy storing
-structural
-communication
-modular incorporation
WE CARE ABOUT D

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2
Q

Monosaccharide

A

-smallest unit of carbohydrate
1. polyhrdroxy aldehydes (aldoses)
2. polyhydroxy ketones (ketoses)
-must contain 3 carbon atoms
-suffix -ose used in nomenclature
aldose most oxidized is C-1
ketose most oxidized is C-2

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3
Q

Oligosaccharide

A

-polymers 2-20 monosaccharide residues

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4
Q

Polysaccharides

A

-polymers contain more than 20 residues

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5
Q

Trioses

A
  • Glyceraldehyde

- Dihydroxyacetone

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6
Q

Cyclization of Aldoses and Ketoses

A

reaction of a hydroxyl with either the aldehyde or ketone results in hemiacetal or hemiketal (ketone)

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7
Q

furanose

A

5 membered ring

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8
Q

pyranose

A

6 membered ring

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9
Q

anomeric carbon

A

C-1 carbon
either alpha or beta
beta is best! OH on top
alpha is bottom

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10
Q

Cyclization of carbohydrate

A

carby C can either be attacked by C4 OH or by C5 OH

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11
Q

sugar phosphate

A

-one of the hydroxyls is converted to a phosphate ester
-numbered according to the carbon it is attached to
alpha-D-Ribose 5 phosphate

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12
Q

Deoxy sugars

A

-a hydrogen replaces the hydroxyl in the parent sugar
-loss of chiral center
beta-2-deoxy-D-ribose

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13
Q

Amino sugars

A

-amino group replaces the hydroxyl in parent
-often not numbered
alpha-D-glucosamine

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14
Q

Sugar alcohols

A

-the carbonyl of the parent sugar is reduced to an alcohol
-replace -ose with -itol
glycerol

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15
Q

sugar acids

A

Two choices:
oxidize the top to a carby from aldehyde
oxidize the bottom to a carby

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16
Q

Disaccharides

A

two monomers connected through a glycosidic bond at the anomeric carbon
-product is a glycoside!

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17
Q

reducing and non reducing sugars

A

-hemiacetals are reducing
-able to reduce metal ions and other friends.
-hemiketal cannot do this
glucose, maltose, cellobiose, lactose and more

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18
Q

polysaccharides

A

homoglycans–one kind of monomer

heterogylcans–several kinds of monomers

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19
Q

Homoglycans

A

starch, glycogen

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20
Q

Starches

A

amylose Glc alpha (1–>4)

amylopectin Glc alpha (1–>4) and branches every 25 residues (1–>6) (300-600 residues)

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21
Q

glycogen

A 
Glc alpha (1-->4) and branches (1-->6) 
smaller and more frequently branches than amylopectin. every 8-12 residues branches (50,000 residues)
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22
Q

Structural homoglycans

A

cellulose

chitin

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23
Q

Cellulose

A 
Glc beta (1-->4)
cell walls. lots of H bonding
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24
Q

Chitin

A

GlcNAc (acetylglucosamine) beta (1–>4)
insects, fungi, red algae
fibrils of

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25
Heteroglycans
Glycosaminoglycans | Hyaluronic Acid
26
Glycoconjugates
- polysaccharides covalently bound to proteins or peptides | - proteoglycans, glycoproteins, glycoconjugates
27
Proteoglycans
- complexes of proteins and glycosaminoglycans chains | - connective tissue
28
glycoproteins
- diverse! - enzymes, hormones, structural proteins, transport proteins - outer plasma membrane - N linked or O linked ( alpha/beta position is stuck to an amine or to oxygen)
29
peptidoglycans
-polysaccharides linked to small peptides -cell walls in bacteria MurNAc-beta-(1-->4)-GlcNAc-beta-(1-->4)
30
Bacterial peptidoglycan
- nice bacteria net over the membrane | - D ala D ala needs a transpeptidase that attaches the pentaglycine portion. Penicillin inhibits this enzyme
31
Lipids
-water insoluble organic molecules -hydrophobs or amphiphilic--polar and nonpolar regions FOUR CLASSES: 1. fatty acids 2. phospholipids 3. glycosphingolipids 4. isoprenoids
32
Lipid nomenclature
-carby group is C1 -name main chain -delta n for unsaturations -shorthand is like this 18 : 1 delta 9 means 18 carbon chain, 1 unsaturation, at the 9 to 10 carbon -hydrocarbon tail (C2) group begins with alpha. last carbon is omega
33
Fatty acid unsaturation
- create a kink in the hydrophobic chain - don't pack as tight, more fluid - cis or trans - usually every three bonds
34
triacylglycerols
-three fatty acids esterified with one molecule of glycerol -highly hydrophobic FATS long chain unsaturated fatty acids OILS short chain unsaturated fatty acids
35
Metabolism of triacylglycerols
- lipases--enzymes that break down dietary lipids | - most fat is stored in adipose tissue
36
Glycerophospholipids
-compose the majority of membranes -amphiphilic molecules: polar head and nonpolar tail -several subclasses phosphatidates plasmalogens
37
Phosphatides
-glycerol backbone -fatty acid at C1 -C2 is unsaturated -phosphate at C3 other classes vary with what fxnal group is esterified to the other OH on the phosphate
38
Phospholipases
- class of enzymes that catalyze the cleavage of esters in phospholipids - can be used to find the structure of a lipid by cutting it up!
39
Plasmalogens
C1 substituent is linked by a vinyl ester CH=CH after the fatty acids linkage Important in the central nervous system
40
Sphingolipids
-after glycophospholipids, most abundant in plants and animals -CNS -sphigosine backbone as you count across: 18 C chain, C2 amine C4-5 trans double bond CERAMIDE fatty acid at C2, precursor for other sphingos 1. Sphingomyelins 2. Cerebrosides 3. Gangliosides
41
Sphingomyelins
- phosphocholine at C1 (otherwise same as the ceramide) | - major component of myelin sheath surrounding nerve cells
42
Cerebrosides
-a monsaccharide is attached through B- glycosidic bond -abundant in nerve tissues and myelin sheaths (15%) -different subclasses depending on ID of the sugar galactocerebroside glucocerebroside
43
Gangliosides
-linked to complex oligosaccharides -containing NeuNAc contains a carby acid, polar head is anionic -protrudes into ECM, function as cell surface markers
44
Steroids
-third class of lipids -isoprenoids -four ring structure -derived from squalene -hydrophobs essential role in mammalian biochemistry
45
Waxes
-nonpolar esters of long chain fatty acids and long chain monohydroxylic alcohols
46
Eicosanoids
-oxygenated derivatives of C20 polyunsaturated fatty acids | prostaglandins have a cyclopentane ring
47
Biological membranes
- essential component of cells and have a variety of functions - separate cellular components - generate and maintain ion and small molecule gradients - biosynthesis and delivery of transmembrane proteins ER
48
Lipid bilayers
main structural component of biological membranes, proteins and carbohydrates 5-6 nm thick, two sheets together
49
Biological membrane composition
-lipid-protein ratio is 25-50% lipid 50-75% protein
50
Plasma membrane
- cholesterol with glycosphingolipids form lipid rafts - lipid ocean, with protein ice bergs floating about - oligosaccharide chains for recognition and signaling
51
Membrane fluidity
-Lateral diffusion and Transverse Diffusion TWO ENZYMES: -Flippase takes outside to inside -Floppase takes inside to outside
52
Membrane Fluidity
Affected by: 1. increase in temp 2. unsaturation 3. amount of cholesterol (20-25% of animal membrane lipids) -decrease fluid at high -increase fluid at low HELP organisms cope in vastly different environments
53
Liposomes
- synthetic vessels composed of lipid bilayers | - great method for drug delivery
54
Classes of membrane proteins
-Integral membrane proteins: spans the membrane completely *includes pores and channels -Peripheral proteins: associated with one face of the membrane through charge to charge interactions -Lipid-Anchored Membrane proteins tethered to a membrane through a covalent bond to a lipid anchor
55
Thermodynamics of Membrane Transport
1. Concentration Gradient (doesnt apply to charged things) | 2. Membrane potential CHARGE
56
Passive transport
movement of a solute down its concentration gradient without expenditure of energy also called facilitated diffusion
57
Active transport
requires energy to move a molecule against the concentration gradient typically uses ATP 1. Primary Active 2. Secondary Active
58
Primary Active
- different source of energy | - ATP or light
59
Secondary Active
- ion conc gradient | - coupled to something that is primary active transport
60
Endocytosis and Exocytosis
- large molecules like proteins cannot diffuse across membrane - Endocytosis: macromolecule engulfed by plasma membrane and brought inside with lipid vesicle - Exocytosis: lipid vesicle fuses to membrane, releasing contents to the outside of the cell
61
Blood Groups
``` H antigen -can be modded by A or B enzyme A adds a GalNAc B adds a Gal D Different oligosaccharides on cell surface! ```

Med Chem (3 decks)

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