1
Q
A
2
Q
General properties: Aromatic compound
A
Typically unreactive, highly stable
Often non-polar and hydrophobic
High carbon-hydrogen ratio
3
Q
Aromatic Nomenclature
A
Substituent bearing carbons numbered first
Numbering ties can be broken by prioritizing the substituent that comes first alphabetically
If ring is not the parent chain, it is treated as a substituent and given the name phenyl
4
Q
Nucleophilic Attack
A
A Nucleophile (Region of electron density) attacks an electrophile (electron-deficient) group
EX: Amine group electron dense, Carboxyl group electron deficient
5
Q
Condensation reactions
A
Two molecules combine (addition) with the release of water (elimination)
EX: peptide bond formation
6
Q
Hydrolysis reaction
A
Addition of water to break a covalent bond
EX: Glycosidic bond cleavage
7
Q
Redox reaction
A
Electron transfer between molecules
Ex: Dehydrogenase enzymes, electron transport chain reactions
8
Q
Isomerization reactions
A
Rearrangement of bonds within a molecule
Ex: Glucose-6-phosphate to Fructose-6-phosphate
9
Q
Transfer reactions
A
Transfer of chemical group (Phosphate, methyl) from one molecule to another
Ex: phosphorylation of proteins
10
Q
Decarboxylation reactions
A
Removal of CO2 from a molecule
Ex: Krebs cycle (aKG to succinyl-CoA), puruvate to acetyl-CoA
11
Q
Carboxylation
A
Addition of CO2
Ex: reverse glycolysis (Glyconeogenesis)
12
Q
Hydroxyl group reactions
A
H bonding, phosphorylation, nucleophilic attack (L functions as nucleophile
13
Q
Carbonyl reaction
A
Nucleophillic attack (carbon electrophile)
Ex: carbohydrate cyclic action
14
Q
-COOH reactions
A
Condensation
15
Q
Amine
A
Nucleophilic attack, N nucleophile
16
Q
Thiol /Sulfhydryl
A
Redox reaction (Disulfide bond formation)
17
Q
Ester
A
Subject to hydrolysis reactions where carbonyl carbon is a strong electrophile
Ex: DNA reaction/ structures
18
Q
Carbohydrate general formula
A
(CH2O)n
N= 3-9 for monosaccharides
19
Q
Aldoses
A
Aldehyde functional group
20
Q
Ketone
A
Ketone functional group
Fructose
21
Q
Oligosaccharides
A
2-10 saccharide chain
22
Q
Polysaccharide
A
Long chain, complex carbohydrates
Ex: cellulose, starch, glycogen
23
Q
Epimers
A
Diastomers that differ around one stereo enter
24
Q
Furanose
A
5 member ring
25
Pyranose
6 member ring
26
Mutarotation
Change of configuration about the anomeric carbon
27
Why is chair confirmation preferred
Prevents crowding of substituents reducing steric strain
28
Large groups prefer which conformation in carbohydrate ring
Equatorial, avoids 1,3 diaxial clashes
29
Reducing sugars
Small carbohydrates containing one or two sugar units that can act as reducing ages toward metal salts such as Ag+ and CU2+
30
Reducing aldehydes
Easily oxidized due to additional H compared to ketose, either chemically or enzymatically, results in the conversion of its aldehyde group to a carboxylic acid
31
Clinical tests that reduce
Tollens: Ag+
Benedicts: Cu2+
Oxidation of aldehydes drive colorimetric change to detect aldose sugar
32
Tautomers
Molecules (constitutional Isomers) that can readily interconvert
33
Glycosidic bonds
Condensation reaction, thermodynamically unfavorable, typically enzyme driven process, couple to high-energy molecule
34
Maltose
Glucose alpha 1,4 glycosidic bond to another glucose
35
Sucrose
Glucose alpha1, beta2 glycosidic bond to fructose
36
Glycogen
Frequent branching, increases solubility, more sites to break down
37
Glycoprotein functions
Sellular protein distribution, cell adhesion, cell recognition
38
Fat soluble vitamins
ADEK
39
Major Functions of lipids
Structural (membranes: phospholipids, cholesterol)
Energy provision or storage (triglycerides)
Signaling (sphingolipids, steroids, vitamins)
40
41
Major properties of most lipids
Significant # of C-H bonds
Generally hydrophobic
Most lipids are amphipathic (Hydrocarbon = hydrophobic tail) with hydrophilic head
Do not form large covalent polymers like proteins, nucleic acids
Associate with other lipids via entropy driven hydrophobic effect and VDW effect btwn hydrocarbons
42
43
Fatty acid composition
Carboxylic acid long-chain hydrocarbon side group
Occur in esterified form as major components
Most between 14-20 carbons
Simplest lipids
44
Saturated fatty acids
Single bonds
Solid at room temp
Linear, packed molecules
45
Unsaturated fatty acid
One or more c=c double bonds
Lower melting and boiling point
Cis configuration causes kinking, more stable due to less steric strain
46
Saturated vs Unsaturated fatty acid fluidity
Fluidity decreases as carbon chain length increases
Fluidity decreases as the number of cis double bonds decreases
(Less kinked = more solid)
47
Oleic (unsaturated fatty acid)
Cis-9-Octadecenoic
abbreviation: 16: 1c (delta) 9
Melting point: 16 Celsius
48
Palmitoleic Unsaturated fatty acid
Cis-9-Hexadecenoic
abbreviation: 16:1c (delta) 9
Melting point: 0 Celsius
49
Linoleic unsaturated fatty acid
Cis, cis-9,12-Octadecenoic
Abbreviation: 18:2c(delta) 9,12
Melting point: 5 Celsius
50
Linolenic
All-cis-9, 12, 15- Octadecenoic
Abbreviation: 18:3c(delta) 9, 12, 15
Melting point: -11 Celsius
51
If using omega nomenclature
Start on opposite side of chasing from carboxylic acid group
52
Triaclyglycerols (triglycerides) structure and function
Glycerol backbone with ester bonding to fatty acid chains (3)
Function: energy reservoirs
Do not occur in membranes
Extraordinarily efficient for energy because carbonyl carbon in reduced (bound to H) form which yields a lot of energy upon oxidation
53
Triacylglycerol as an energy source
Fats are packed tightly together without water, store far greater amounts of energy in a reduced space
Gram of fate is densely concentrated with energy, contains more than double the amount of energy than a gram of carb
more carbons, more reduced than glucose, therefore more products to enter the krebs cycle
54
Phospholipids
Major constituents of biological membranes
Highly polar head groups, usually two hydrocarbon (fatty acid) tails
55
Phospholipids structure
Phosphate and alcohol comprise the head group
Hydrophobic fatty acid tail
Joined by phosphodiester linkage
Further classified based on the back bone
(Glycerol=glycerophospholipids, sphingosine=sphingophospholipids)
56
Glycerophospholipids structure
Glycerol backbone bonded by ester to link FA
Phophodiester linkage to polar head groups
Amphipathic
(C3 linked to head group)
57
Glycerophospholipids head group: 0 net charge
PE, PC
58
Glycerophospholipids head group: -1 net charge
PA, PS, PG
59
Glycerophospholipids head group: -4 net charge
PI
60
Glycerophospholipids head group in order of size
PA, PE, PC, PS, PG, PI, cardiolipin
61
Cardiolipin
Conical shape= curviture
Inner mitochondrial membrane
Gobbles pitsode of cell ability to interact with aqueous solution
4 fatty acid chains, 2 glycerol backbone, phosphate head group
62
Sphingolipids
Membrane constituents
Can or may not be phospholipids
Derivatives of 18 C unsaturated, amino alcohol sphingosine
Sphingosine is backbone
FA linked to amino alcohol sphingosine via an amide bond to form ceramide
63
Ceramide
Sphingosine + FA
Amide bond linkage (gives it strong, resonance stabilization)
64
Ceramides function
Commonly used as precursors for more abundant sphingolipids
65
Ceramide structure
Fully saturated with 14-26 carbons with sphingosine (unsaturated backbone) amide bonding to FA,
66
Ceramide function/ properties
High phase transition temperature
Key to signaling processes, may serve as second messengers
67
Sphingomyelin structure
Head group: PE or PC
Long hydrophobic tails (14-24)
Amide bonding is particularly strong
68
Sphingomyelin Function
Primarily component of cell membrane of cells producing myelin sheath for axons
Decreased fluidity due to long Carbon chain length
Less permeable barrier for ions = better insulation for axons
69
Glycosphingo lipids
Glycans (sugars) attached to sphingosine
Simplest version has a single sugar (monoglycosphingolipid AKA cerebroside)
Includes cerebrosides and gangliosides
70
Gangliosides
Ceramide oligosaccharides that include at least one aiolis acid residue
Complex Carbohydrate head groups
71
Ganglioside s
72
Name, D or L, type of carb
D-Fructose, Ketose
73
Name, D or L, functional group
D-glucose, aldose
74
Name, D or L, type,
D-ribose, aldose, Pentose
75
Name, D or L, functional group
D-Galactose, aldose, hexose
76
Name, glycosidic bonding
Alpha D-glucose + Beta D- Fructose = sucrose ; Alpha 1, Beta 2
77
Name, D or L,
D-glyceraldehyde, triose
78
Name, D or L
L-Glyceraldehyde, triose
79
Name, saccharides involved, glycosidic bonding, properties
Isomaltulose, alpha D-glucose + D-fructose, glycosidic bond alpha 1,6
Slower absorption due to glycosidic alpha 1,6 bond. Resulting in lower blood glucose response
80
Which is Beta-D-Galactose involved in the formations of Lactulose
D
81
What is this structure, glycosidic bonding, is it a reducing sugar? If so why
Isomaltulose, alpha 1,6 glycosidic bond. It is a reducing sugar due to its anomeric carbon of fructose is available
82
Carbohydrates contain two important functional groups that can tautomerize when catalyzed by enzymes. Which functional groups?
Aldehydes and ketones
83
A lipid contains a backbone with at least two hydroxy groups, connected to a fatty acid tail via an amide bond. What family of lipids does this belong to?
Sphingolipids
84
What type of lipid
Glycerophospholipids
85
Name this molecule
5, methyl-1, phenyloctane
86
Name
4, phenyloctane
87
Name
4, phenyloctane-2-one
88
Name
2, ethyl-1, methyl- 3,prophylcyclohexane
89
Name
1, methyl-4, pentylbenzene
90
What disaccharide, glycosidic bond?
Lactose: Beta 1,4 glycosidic bond
91
When do you specify the the configuration of the second molecules glycosidic bond like in sucrose a1, B2?
When bond involves the anomeric carbon of the second sugar.
ANE 610
flashcards
Decks in class (8)
# Cards
-
Module 1: Methods/Measurements, Atoms, Periodic Table, Ionic And Covalent compounds61
-
Module2: Calculations, The Chemical Equation, And Solutions45
-
Module 791
-
Module 8143
-
Module 9 Molecular Genetics154
-
Module 10 Carbohydrate Metabolism152
-
Module 11 Aerobic Respiration And Energy Production92
-
Module 12 Fatty Acid Metabolism, Protein Metabolism, Nucleic Acid Synthesis117
