Organic Chemistry, Biochemistry and Biochemical Engineering Flashcards
Who coined the word enzyme first?
Wilhelm Kühne
Substituent effects:
Enumerate Ortho- and Para- Activating Substituents
-Hydroxy
-Alkyl
-Amino
-Alkoxy
-Halogen (-OR)
-Acetamido (-NHCOCH3)
Substituent effects:
Enumerate Meta- Activating Substituents
-Sulfonic Acid
-Carbonyl
-Cyano
-Carboxyl
-Nitro
Zaitev’s Rule
(Definition and when to apply)
“the rich getting richer, the poor getting poorer”
The carbon with the fewest hydrogens loses the hydrogen.
Catalyzed the Biochemical Engineering Field
Penicillin
Most abundant organic compounds in the plant world.
Carbohydrates
These biomolecules are polyhydroxy aldehydes, polyhydroxy ketones, or compounds that can be hydrolyzed to them.
Carbohydrates
What are used in animals as a source of quick energy that can be stored in the liver and muscles?
Carbohydrates
Sugars, starches, and cellulose belong to which major class of biological molecules?
carbohydrates
(CH2O)n is the molecular formula for which type of macromolecules?
Carbohydrates
Plants like sugar cane and sugar beets store the energy as simple sugars. Other plants, like corn and potatoes, store the energy as more complex sugars called?
starches
Monosaccharides chemical formula
Cn(H2O)n
Monosaccharides:
Differentiate Aldoses and Ketoses
Aldoses: contains aldehyde group. Carbonyl (C=O) at C1 (at one end)
Ketoses: contains ketone group. Carbonyl (C=O) at other carbon atom
Enumerate Monosaccharides
ALL ALTruists GLadly MAke GUm In GALlon TAnks
-Allose
-Altrase
-Glucose
-Mannose
-Gulose
-Idose
-Galactose
-Talose
Explain D-L stereochemistry of Carbohydrates
*Emil Fischer
Dextrorotatory – highest numbered chiral carbon on right side
Levorotatory - highest numbered chiral carbon on left side
Can also be based on penultimate carbon (2nd to last)
What are chiral carbons?
Carbon connected to four different functional groups
Describe anomers, alpha and beta anomers
Anomeric carbon - Carbon in ring attached to hydroxyl group (-OH)
Alpha anomer = trans configuration
Beta anomer = cis config, more contributing
Bonds between monosaccharaide units
Glycosidic bond
Which of the following is NOT a polysaccharide?
A. Glycogen
B. Starch
C. Sucrose
D. Cellulose
Sucrose
Oligosaccharides vs Polysaccharides
Oligosaccharides: 6 to 10 monosaccharide units
Polysaccharides: >10 monosaccharide units
Found in cell walls of nearly all plants where it gives support and rigidity to plant stems.
ADDITIONAL: What is its composition?
Cellulose
20% amylose, 80% amylopectin
Main carbohydrate found in the seeds and roots of plants.
Starch
Enumerate Disaccharides (and combinations)
1) Sucrose
- Glucose + Fructose
- a-1,2-glycosidic bond
- From sugar cane and photosynthetic plants
- Only non-reducing sugar (negative Fehling’s)
2) Maltose
- Glucose + Glucose
- from hydrolysis of starch
- a-1,4-glycosidic bond.
3) Lactose
- Glucose + Galactose
- b-1,4-glycosidic bond
4) Cellobiose
- from partial hydrolysis of cellulose
- Beta-Glycosidic Linkage
Differentiate bonds in Disaccharides:
Sucrose
Lactose
Maltose
Cellobiose
Sucrose: a(1–>2)
Lactose: B(1–>4)
Maltose: a(1–>4)
Cellobiose: B(1–>4)
Describe Sucrose
1) Sucrose
- Glucose + Fructose
- From sugar cane and photosynthetic plants
- Only non-reducing sugar (negative Fehling’s)
Describe Maltose
2) Maltose
- Glucose + Glucose
- from hydrolysis of starch
- Alpha-Glycosidic Linkage
Describe Lactose
3) Lactose
- Glucose + Galactose
- Beta-Glycosidic Linkage
Describe Cellobiose
4) Cellobiose
- from partial hydrolysis of cellulose
- Beta-Glycosidic Linkage
Most abundant disaccharide in the biological world.
Sucrose
Describe the following Polysaccharides:
Starch
Amylose
Amylopectin
Glycogen
Celulose
*Starch - energy storage for plants. Can be separated into two fractions: amylose and amylopectin
* Amylose - 1,4-ALPHA-glycosidic bonds
* Amylopectin - branching with 1,4-ALPHA-glycosidic bonds & 1,6-ALPHA-glycosidic bonds
* Glycogen - energy storage for animals. similar structure to amylopectin but more extensive branching
* Celulose -1,4-BETA-glycosidic bonds
Animals stored energy in glycogen, while plants in starch. What is the difference of their structure?
Starch - sugar molecules linked in same interval
Glycogen - branching chains
Proponent of ABO blood group system
Karl Landsteiner
Invert sugar consists of ___ and ___
fructose and glucose
Describe Chemical Characterization of Sugars
Fehling’s Test
Tollen’s Test
Benedict’s Test
Iodine Test
IDENTIFY REDUCING SUGARS
Fehling’s Test: form red ppt
Tollen’s Test: form silver mirror
Benedict’s Test: form brick red ppt
OTHERS
Iodine Test: identify presence of starch. Form blue solution
Molisch’s Test: identify presence of carbohydrates
AMINO ACIDS:
Enumerate amino acids with Non-Polar Side Chains
GAV LIM PTP
* Glycine
* Alanine
* Valine
* Leucine
* IsoLeucinE (ILE)
* Methionine
* (F) Phenylalanine
* (W) Tryptophan
* Proline
AMINO ACIDS:
Enumerate amino acids with Polar Side Chains
STC TAG
* Serine
* Threonine
* Cysteine
* tYrosine
* asparagiNe
* (Q) glutamine
AMINO ACIDS:
Enumerate amino acids with Electrically Charged Side Chains
AG HAL
Acidic:
* (D) Aspartate
* (E) Glutamate
Basic:
* (K) Lysine
* (R) aRginine
* Histidine
Solution used to differentiate between water-soluble carbohydrate and ketone functional groups, and as a test for reducing sugars and non-reducing sugars
Fehling solution
Which macromolecule does not dissolve in water?
lipids
What are the monomers of lipids?
Fatty acids and glycerol
Lipids are used by the body to perform all of the following functions EXCEPT:
A. membrane structural material.
B. enzyme action.
C. insulation.
D. a rich energy source.
enzyme action
________ are the most abundant lipid present in an organism.
Fats / Triacylglycerols
Fats as compared to oils have _____
less unsaturated glycerides of fatty acid
Fats that have fatty acids with only single covalent bonds in their carbon skeletons are ____
saturated
Differentiate Hydrolysable and Non-Hydrolysable Lipids
Hydrolysable Lipids: CAN be cleaved into smaller units
Non-Hydrolysable Lipids: CANNOT be cleaved into smaller units
Describe Waxes
- C16 - C36
- Hydrolysable
- Simplest Hydrolysable Lipid
- ester
- hydrophobic
Describe Triacylglycerol
- Hydrolysable
- Most abundant lipid
- energy storage
- Triesters that produces glycerol and fatty acid
Describe Sphingomyelins
- Hydrolysable
- Component of lipid bilayer
-Found as insulation in nerve cells (myelin sheathes)
Describe Phosphoacylglycerols
- Hydrolysable
- ## 2nd most abundant lipid
Fats are esters derived from fatty acids stored via esterification with glycerol. Due to this reaction, fats are also referred to as:
Glycerides
Glycerides is also known as ___
Triacylglycerols
Triacylglycerides
Unsaturation of the acid chains of a fat results in a/an ________ in their melting point.
Decrease
Defined by their physical properties, NOT by particular functional groups
Lipids
Where in the body does fatty acid synthesis occur?
Cytoplasm and Endoplasmic reticulum
Where in the body does protein synthesis occur?
Ribosome
Lipids that mainly contain ester units. Can be hydrolyzed
Hydrolysable Lipids
Simplest hydrolysable lipids. Formed from alcohol and fatty acid. Hydrophobic.
Waxes
Differentiate Animal fats and Vegetable oils
Animal fats: composed of saturated fatty acids, thus higher melt pt and solid at room temp.
Vegetable oils: composed of unsaturated fatty acids, this lower melt pt. and liquid at room temp.
Hydrolysis of triglyceride to produce glycerol + soap
Saponification
Salt of a long chain carboxylic acid.
Soap
Soaps are _____ produced from the saponification (base hydrolysis) of animal fats (glycerides)
sodium & potassium salts of fatty acid
Common bases for saponification
NaOH or KOH
These are spherical clusters of hundreds of soap molecules:
Micelles
_____ involves the industrial hydrogenation of unsaturated fats (oils) in the presence of nickel catalyst at 175-190 degC and 20-40 psi.
Saturation / Hydrogenation
____ of fat is due to the presence of volatile, bad smelling acids and aldehydes.
Rancidity
Hydrolysis of triglycerides under basic conditions, producing glycerol and soaps
Saponification
Process that turns vegetable oil to margarine
Hardening
Important fats for the body that can be found in eggyolks and soybeans
Lecithin
Lipids important biological regulators that show dramatic physiological effects when administered to living organisms.
Steroids
Enumerate Non-Hydrolysable Lipid
FETS
Fat Soluble Vitamins
Eicosanoids
Terpenes
Steroids
An organic compound required by organisms in minute quantities for growth and reproduction because it cannot be synthesized by the organism; it often serve as enzyme cofactors or parts of cofactors.
vitamin
Explain Fat-Soluble Vitamins
Vitamin A
Vitamin D
Vitamin E
Vitamin K
Non-Hydrolysable Lipid
Vitamins that must be obtained from food, but do not have to be ingested every day.
Vitamin A - Retinol
Vitamin D - Calciferol
Vitamin E - a-Tocopherol
Vitamin K - Phylloquinone
Describe Terpenes
(Hydrolysable? Function? Composition?)
Non-Hydrolysable Lipid
Lipids found in the essential oils of many plants.
Consists of repeating units of isoprene
Describe Eicosanoids
(Hydrolysable? Function? Composition?)
-Non-Hydrolysable Lipid
- Biologically active
-containing 20+ C’s derived from ARACHIDONIC (C20) acid.
Enumerate Saturated Fatty Acids by increasing MW, melting point, boiling point
Laura Makes Pancakes on Saturday Afternoon
Lauric C12 < Myristic C14 < Palmitic C16 < Stearic C18 < Arachidic Acid C20
Describe Steroids
(Hydrolysable? Function? Composition?)
- Non-Hydrolysable Lipid
- Biologically active
- Consists of 3 six-membered rings and 1 five-membered ring joined together
Describe Cholesterol
(Hydrolysable? Function? Composition?)
- Most abundant and most important steroid
- Plasma membrane of animal cells
- Starting material for synthesis of other steroids
Sex hormones are derived from ___
Androgens are for ___
Estrogens for ___
Cholesterol
Males
Females
The main fate of amino acids is the synthesis of ____
Protein
Biomolecule made of long chains of amino acid residues.
Proteins
These biomolecules are polyamides whose monomers from which they are derived are α-amino carboxylic acids known as amino acids.
Proteins
What are described as the “building blocks of Protein”?
Amino Acids
Proteins are ____ made of amino acid _____.
polymers; monomers
Differentiate proteins and peptides
proteins: > 50 amino acids
peptides: < 50 amino acids
____ is a disorder which results from the replacement of one glutamic acid side chain in the hemoglobin molecule by a valine unit.
Sickle-cell anemia
PROTEIN:
Primary, Secondary, Tertiary and Quaternary Structure of Protein
Primary: Amino acid sequence
Secondary: Alpha helix coil or beta sheet
Tertiary: fold of proteins
- #d shaped adopted by the entire peptide chain
Quaternary: polypeptide chains
The local spatial arrangement of a polypeptide’s backbone atoms without regard to the conformation of its side chains can be called as ___
Secondary structure
The primary stabilizing force of protein secondary structure is:
Hydrogen bonds
In this type of structure, most of carbonyl groups of peptide bonds forms a hydrogen bond with the amide nitrogen of another peptide bond four amino acids further down the polypeptide chain:
Alpha-helix
The alpha helix found in myoglobin can best be described as
Secondary structure
The action of disrupting the threedimensional shape of a protein is termed ___
denaturation
Enumerate the Essential Amino Acids
PriVaTe TIM HALL (PVT TIM HALL)
Phenylalanine
Valine
Tryptophan
Threonine
Isoleucine
Methionine
Histidine
Arginine (not essential for adults)
Leucine
Lysine
Found in hair, nails and skin
Keratin
Most abundant protein in invertebrates. Also found in bones teeth and blood vessels
Collagen
Where collagen can be found?
found in bones teeth and blood vessels