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Med Chem > Biochem 8-9 > Flashcards

Biochem 8-9 Flashcards

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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
Q

Heteroglycans

A

Glycosaminoglycans

Hyaluronic Acid

26
Q

Glycoconjugates

A
  • polysaccharides covalently bound to proteins or peptides

- proteoglycans, glycoproteins, glycoconjugates

27
Q

Proteoglycans

A
  • complexes of proteins and glycosaminoglycans chains

- connective tissue

28
Q

glycoproteins

A
  • 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
Q

peptidoglycans

A

-polysaccharides linked to small peptides
-cell walls in bacteria
MurNAc-beta-(1–>4)-GlcNAc-beta-(1–>4)

30
Q

Bacterial peptidoglycan

A
  • nice bacteria net over the membrane

- D ala D ala needs a transpeptidase that attaches the pentaglycine portion. Penicillin inhibits this enzyme

31
Q

Lipids

A

-water insoluble organic molecules
-hydrophobs or amphiphilic–polar and nonpolar regions
FOUR CLASSES:
1. fatty acids
2. phospholipids
3. glycosphingolipids
4. isoprenoids

32
Q

Lipid nomenclature

A

-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
Q

Fatty acid unsaturation

A
  • create a kink in the hydrophobic chain
  • don’t pack as tight, more fluid
  • cis or trans
  • usually every three bonds
34
Q

triacylglycerols

A

-three fatty acids esterified with one molecule of glycerol
-highly hydrophobic
FATS long chain unsaturated fatty acids
OILS short chain unsaturated fatty acids

35
Q

Metabolism of triacylglycerols

A
  • lipases–enzymes that break down dietary lipids

- most fat is stored in adipose tissue

36
Q

Glycerophospholipids

A

-compose the majority of membranes
-amphiphilic molecules: polar head and nonpolar tail
-several subclasses
phosphatidates
plasmalogens

37
Q

Phosphatides

A

-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
Q

Phospholipases

A
  • 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
Q

Plasmalogens

A

C1 substituent is linked by a vinyl ester
CH=CH after the fatty acids linkage
Important in the central nervous system

40
Q

Sphingolipids

A

-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
Q

Sphingomyelins

A
  • phosphocholine at C1 (otherwise same as the ceramide)

- major component of myelin sheath surrounding nerve cells

42
Q

Cerebrosides

A

-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
Q

Gangliosides

A

-linked to complex oligosaccharides
-containing NeuNAc
contains a carby acid, polar head is anionic
-protrudes into ECM, function as cell surface markers

44
Q

Steroids

A

-third class of lipids
-isoprenoids
-four ring structure
-derived from squalene
-hydrophobs
essential role in mammalian biochemistry

45
Q

Waxes

A

-nonpolar esters of long chain fatty acids and long chain monohydroxylic alcohols

46
Q

Eicosanoids

A

-oxygenated derivatives of C20 polyunsaturated fatty acids

prostaglandins have a cyclopentane ring

47
Q

Biological membranes

A
  • 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
Q

Lipid bilayers

A

main structural component of biological membranes, proteins and carbohydrates
5-6 nm thick, two sheets together

49
Q

Biological membrane composition

A

-lipid-protein ratio is 25-50% lipid 50-75% protein

50
Q

Plasma membrane

A
  • cholesterol with glycosphingolipids form lipid rafts
  • lipid ocean, with protein ice bergs floating about
  • oligosaccharide chains for recognition and signaling
51
Q

Membrane fluidity

A

-Lateral diffusion and Transverse Diffusion
TWO ENZYMES:
-Flippase takes outside to inside
-Floppase takes inside to outside

52
Q

Membrane Fluidity

A

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
Q

Liposomes

A
  • synthetic vessels composed of lipid bilayers

- great method for drug delivery

54
Q

Classes of membrane proteins

A

-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
Q

Thermodynamics of Membrane Transport

A
  1. Concentration Gradient (doesnt apply to charged things)

2. Membrane potential CHARGE

56
Q

Passive transport

A

movement of a solute down its concentration gradient without expenditure of energy
also called facilitated diffusion

57
Q

Active transport

A

requires energy to move a molecule against the concentration gradient
typically uses ATP
1. Primary Active
2. Secondary Active

58
Q

Primary Active

A
  • different source of energy

- ATP or light

59
Q

Secondary Active

A
  • ion conc gradient

- coupled to something that is primary active transport

60
Q

Endocytosis and Exocytosis

A
  • 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
Q

Blood Groups

A 
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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