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Orgo2 > Lipids Terms > Flashcards

Lipids Terms Flashcards

1
Q

fatty acid

A

carboxylic acid with long hydrocarbon tail

(natural fatty acids any unsaturation is always cis)

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2
Q

melting points are affected by

A

unsaturation and chain length

more double bond the the lower the melting point
and the longer the chain the higher the melt point

cis usually has a lower melt point than trans

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3
Q

monounsaturated fat

A

one double bond

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4
Q

polyunsaturated

A

two or more double bonds

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5
Q

hydrophobic nature comes from the presence of….

A

the long hydrophobic tails

they are insoluble until the COO- is ionized

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6
Q

is acetic acid a fatty acid?

A

no despite being a short carboxylic acid it is not

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7
Q

pka of the carboxyl is

A

5

it remains mostly unionized but a little bit is and it decreases the pH of the water

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8
Q

some polyunsaturated fats that humans cannot synthesize:

A

Linoleic acid
alpha linoleic acid (ALA)
Eicosapentaenoic acid (EPA)
Docosahexaenoic acid (DHA)

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9
Q

How to name:

A

ex 18:2 and omega 6 fatty acid

18 carbon, 2 double bonds
count carbons from the tail to the first degree of unsaturation (right to the double bond)

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10
Q

waxes

A

are usually monoesters of long chained fatty acids

(secreted from waterproof coating)

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11
Q

Nucleophilic acyl substitution

A

is a type of substitution reaction involving an acyl group and a nucleophile.

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12
Q

how are fats found in the body

A

they are never free they are always found as triglycerides

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13
Q

fats are solids and oils are liquids what determines this

A

highly saturated fats are solids (bc they are better at packing)

unsaturated means its an oil

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14
Q

how are triglycerides hydrolyzed?

A

under acidic or basic conditions (they hydrolysis of esters)

break into the glycerol and fatty acid

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15
Q

acids are

A

proton donors

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16
Q

bases are

A

proton acceptors

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17
Q

How many carbons are in fatty acids in biological systems

A

almost always an even number
12-24 mostly commonly 16-18

they are synthesised as esters

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18
Q

How are long fatty acids generated?

A

joining together multiple acetyl units together

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19
Q

Claisen condensation

A

a nuc acyl substitution reaction using carbanions

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20
Q

reductions

A

gain H’s

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21
Q

oxidations

A

lose H’s

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22
Q

why can’t the biosynthesis be identical to the lab synthesis?

A

bc NaBH4, conc H2SO4, and H2/pt dont exist biologically

claisen rxn have small equilibrium constants
(in the lab we can make the products more favourable by adding strong base to deprotonate the alpha H)
(biological solutions preform a modified claisen type condensation using a more reactive acid derivative and carbanion equiv

acetate units are added one at a time to prevent the growing chain from diffusing away until the desired length is reached

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23
Q

Modifications for the biosynthesis of fatty acids

A

-use thioesters instead of oxygen esters bc they are more reactive (larger) and therefore a better leaving group

-use carbanion equivalents
by using the malonyl thioester the carbanion equiv the enolate is avoided completely

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24
Q

how is the malonyl thioester made

A

using an acetyl thioester using ATP and biotin and an CO2 carrier

the samae co2 that is lost is added

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25
Q

what does the ACP prevent

A

the diffusion problem

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26
Q

what is the ACP made of

A

vitB5-pantothenic acid and other components with a thiol group

the new piece is on the ACP

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27
Q

what is the FAS

A

where the rxn are done which contains a thiol group

ACP is strong bound to the FAS so the growing chain does not float away until purposefully detached

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28
Q

where is the electrophile and the nucleophile

A

the acp has the nuc and the one above has the electrophile

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29
Q

the electrophile is

A

always the growing thioester chain and it grows at the thioester end

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30
Q

the nuc is always the

A

malonyl thioester regardless of the growing chain

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31
Q

the synthesis includes

A

red, dehydration, red

32
Q

why can the reduction of the bete carbon occur

A

bc the beta carbon has positive character and is electrophilic

33
Q

michael addition

A

the conjugate addition
bc you add a H to the beta carbon and then move the double bond

34
Q

what is the normal product of fatty acid biosynthesis

A

palmitic acid

35
Q

what does desaturase ensymes do

A

introduce a cis alkene using atmospheric o2 as an oxiding agent

36
Q

what enzyme performs the hydrolysis of the triglycerdies in our body?

A

lipase

37
Q

the products of a hydrolysis

A

glycerol and 3 fatty acids

38
Q

what happens to the glycerol

A

it is phosphorylated and then oxidized by NAD+ (loses H)

39
Q

what happens to the fatty acid

A

It undergos beta oxidation
degraded into acetyl CoA where the beta carbon is oxidized from an alkyl carbon to a ketone

40
Q

alpha carbon is

A

more acidic and therefore removed first

41
Q

NAD+

A

oxidizes (takes a H)

42
Q

what are soaps

A

they are metal salts of fatty acids, prepared by the hydrolysis of triglycerides

43
Q

soaps are hydrolyzed by what

A

by a base (NaOH)

44
Q

what is a micelle

A

individual soap molec aggreagates to that are spherical structure

form bc the hydrophobic tails are attracted to each other bia hydrophobic forces

they are not tightly packed so dirt can enter and can act as a cleaning agent

45
Q

soaps are considered

A

natural bc they are made of naturally occuring molecs

46
Q

detergents are

A

synthetic

47
Q

why were detergents developed

A

bc they wanted to solve the problem of hard water

they have a hydrophobic head which is not a carboxylate group

48
Q

what is a problem with soaps

A

the carboxylates precipitate out in the presence of polyvalent ions (Ca2+, Mg2+ etc)

49
Q

how are detergents catergorized

A

based on the nature of the hydrophilic head

50
Q

anionic

A

first detergents developed
the alkybensene sulfonates
starting materials were cheap

12 c tail was found to be ideal

51
Q

problem with anionic detergents

A

the alkyl chain was not biodegradable
they have been replaced by linear tails (but these are more expense to make)

52
Q

ex of an anionic detergent

A

SDS

53
Q

cationic detergents

A

typically quaternary ammonium salts
the are usually antimicrobial and found in disinfectants

54
Q

non-ionic

A

contain hydrophilic heads without a formal charge (polar head)

55
Q

additives

A

helps stop making clothes grey bc of the metal residue

2 types
phosphate additives
slicates

56
Q

phosphate additives

A

chelating the positively charged ions
but was suffocating organisms by reducing the amt of o2 bc it is also a fertilizer

57
Q

silicates

A

functionally similar to phosphate additive but safer

58
Q

phosphoglycerides

A

are phospholipids that are found almost exclusively in plants and animal cells

structure is phosphatidic acid and glycerol and 2 fatty acids

fatty acids are a mic of saturated and unsaturated to give the semi fluid nature of membranes

the phosphatidic acid backbone is esterified to the second alcohol at the phosphate forming a phosphodiester

59
Q

phospholipids form

A

bilayers where as soaps form micelles

they also have an extra tail to pack together tightly they are not leaky like soaps

60
Q

terpenes

A

lipids defined by solubility
5 carbon atoms

61
Q

isoprene units and related linkages

A

2 units: 1 head to tail
3 units: 2 head to tail …

30- 2 15 carbon tail to tail
40-2 20 carbon tail to tail

62
Q

DMA-OPP

A

electrophile double bond in the middle

63
Q

IP-OPP

A

nucleophile double bond on the top left

64
Q

max size of isoprene is

A

20 carbons which can then be used to make a diterpene or sesquiterpenes (15 carbons)

65
Q

dimerization to make C30 or C40

A

uses NADPH and

66
Q

the origins of DMA-OPP and IP-OPP

A

made from Beta keto thioester

67
Q

Aldol rxn

A

‘Aldol’ is an abbreviation of aldehyde and alcohol. When the enolate of an aldehyde or a ketone reacts at the α-carbon with the carbonyl of another molecule under basic or acidic conditions to obtain β-hydroxy aldehyde or ketone, this reaction is called Aldol Reaction.

68
Q

what is the intermediate relating the aldol condenstaion product and the IP-OPP is called

A

mevalonic acid

69
Q

why is the b keto attacked and not the enolate

A

it is more electrophilic bc the other side is more resonacne stabilize bc of the SR

70
Q

steriods

A

plant and animal lipids
tetracyclic fused ring system: 3 6 membered rings and one 5 membered ring

fused trans and h and CH3 are trans

planar, rigid structure and flatness is for cell membrane componets takes up leasespace

71
Q

what are steriod synthesised from

A

terpenes not fatty acids

72
Q

lanosterol

A

is a compound used for the synthesis of many other steroids

an intermediate to cholesterol

7 chiral centers

one one sterioisomer is formed bc there two enzymes put the stuf in the correct position

most stable as chair boat chair

73
Q

Fat soluble vitamins

A

A, D, E, K

74
Q

Vit A

A

made from beta carotene
can accumulate in the body

75
Q

Vit E

A

is an antioxidant bc it has a phenolic OH

it gives itself up so our cells arent oxidized

76
Q

What is BHT

A

synthetic antioxidant food preservative

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