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Amino Acids/proteins
Amino Acids/proteins
Amino acids/Proteins
Chapter 17
Protein - More than an Energy Source
H dehydration
H2N CH C OH + H N CH C OH
hydrolysis
CH3 H
alanine (ala) glycine (gly)
O O
H
H2 N CH C N CH C OH + H2O
Ile - Gln
Vasopressin - diuretic
Tyr Asn
Cys Cys - Pro - Leu - Gly
S-S
Val-Ile-Gly Insulin (21 + 30)
Glu
Gln
Cys Cys-Ser-Leu-Tyr-Gln-Leu-Glu-Asn-Tyr-Cys-Asn
Cys-Thr-Ser-Ile
Cys-Gly-Ser-His-Leu-Val-Glu-Ala-Leu-Tyr-Leu-Val-Cys-Gly
Leu Glu
His Arg
H-bonding -
intramolecular
Tertiary Structure of Proteins
• Arises from weaker attractive forces (non
polar dispersion forces) between
hydrophobic parts of the same chain that are
widely separated in the primary structure,
but close in space
• “intramolecular”
• Results in chain twisting and folding
Dispersion forces
• Attractive when nuclei are separated by the
sum of their van der Waals radii
Tertiary structure of protein:
braids and globs
• Collagen-a fibrous protein (precursor of
gelatin) has a triple helix structure-some
elasticity due to interchain interactions
• Hemoglobin (a globular protein)
Tertiary Structure (30) - braids & globs
collagen
hemoglobin
Hemoglobin(H) and Myoglobin (M)
• H has 4 polypeptide chains : carries O 2, CO2
and H+ in the blood, and possesses
quaternary structure
• M has a single chain of 153 amino acids:
carries O2 from the blood vessels to the
muscles and stores it until needed.
• Both have Fe II containing heme unit in
each chain that binds O2.
Myoglobin Structure
To summarize
• Myoglobin cannot have quaternary
structure since it has only one polypeptide
chain
• Hemoglobin has 4 polypeptide chains and
possesses quaternary structure
Enzyme structure
• Many enzymes are proteins and their
specific binding properties to a substrate
depend on their overall molecular shape or
“conformation”
Lock and key mechanism for activity
Active Site of Enzymes
Denaturation -
any physical or chemical process that changes
the protein structure and makes it incapable of
performing its normal function.
Whether denaturation is reversible depends
on the protein and the extent of denaturation.
Examples:
heating egg whites (irreversible)
‘permanent’ waving of hair (reversible)
Protein Chemistry and your hair
• Forces combining to keep hair (a) straight
(b) in loose waves or (c) in tight curls are:
HSCH2COOH
H2O2
Use some Protein Chemistry on
your hair!
• Slightly basic solution of thioglycolic acid is used:
cleaves the disulfide links and makes new SH
bonds (reset hair)
• Then Dilute! Peroxide used in final Oxidation step
of “perm” (otherwise bleaching effect!)
Simple Conjugated
Fibrous
Collagens Elastins Keratins Myosins
Globular
Albumins Globulins
• Nutr aceutical
Tryptophan therapy
• For sleep disorders
Other foods with tryptophan
25
Problem Set #4
• Chapt 17# 1,3,4,5,11,14,15,22
CHEMISTRY of COOKING
• Why is my toast brown?
• What happens to meat when it is cooked?
• What causes the odour of roasted meats?
• What causes the flavour of roasted coffee?
• Does cooking introduce harmful
byproducts?
WHY COOK AT ALL?
• It tastes (and smells) good
• Food is made more digestible and allows us
to eat a greater range of food
• Releases the raw materials that we might
otherwise not be able to digest (ie. in meat)
• Cooking destroys bacteria such as
salmonella, E coli etc., thus more safe
Let’s compare
• Grilling (BBQ) gas or with hard wood
coals: char broiled
• Oven broiled
• Oven roasting (baked)
• Boiled
• Steamed
• Microwave
Your thoughts?????
What is known for sure
• BBQ (Grilling) of high fat content meats at
high temp produces Polynuclear aromatic
hydrocarbons (PNAH’s)
• Planar molecules: intercalate into the major
groove of the DNA double helix
• Can be cancer inducing if DNA directed
synthesis of protein gets out of control
First cancerous lesions
• Observed in chimney sweeps in UK in
1700’s and workers in coal tar industry
• Exposure to soot on skin
• PNAH’s common in soot from burning of
coal
Some structures of PNAH’s
That BBQ steak flavour
• 15 different PNAH’s have been isolated from the
outer layer of charcoal broiled steak
• 8 micrograms of 1,2-benzopyrene per kilo of steak
• Arise from decomposition of fat that drips on to
the glowing charcoal and the subsequent
vaporization of the hydrocarbons and deposition
on the surface of the meat
Other possible carcinogens
• Heterocyclic amines (HCA’s) added to list
of known carcinogens in 2005
• Arise from reaction of creatine (an amino
acid found in muscle) and carbohydrate
• Higher temps from grill, frying or oven
broiling increase the concentrations
How to minimize these risks
• Use lean meats or remove fat
• Cook at lower temperatures (ie allow coals
to cool to embers if using hardwood) or on
a gas grill move food to an upper rack
• Use marinades (olive oil or citrus based)
• Avoid overcooking
Marination: also denaturation
• Long time (days) exposure to acid (in
vinegar) will denature some protein and
tenderize some meat
• Also kills Salmonella, but not E coli
Cooking fish on the grill
• Leave skin on and do most of the grilling
skin side down–easily separated when fish
is cooked
• Use cedar grilling planks to impart a rich
smoky flavour –keeps fish moist and no
charring
Happy BBQ’s (a summer tradition)
• N: C=O
What are the products ?
• Reaction occurs around 300F
• Biscuit, popcorn, bread, tortilla flavour
(odour threshold is 0.06 ng/L)
Can you name this compound?
• Probably not!
• 2-acetyl-3,4,5,6-tetrahydropyridine