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Basic Concepts in Biochemistry
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pH pKa 46 4 [CH3CO2 ] 2 [CH3CO2 ] [CH3CO2H]
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pKa [CH3CO2 ] [CH3CO2H]
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[CH3CO2H]
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Equivalents of Base Added
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Figure 23-4 Titration of Acetic Acid
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At the pKa, the concentrations of acetate and acetic acid are equal
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other (closer than about 2 units), the higher-pKa group starts titrating before the lower-pKa group finishes, and there are no sharp transitions between the two titrations This is most obvious for the titration of glutamate, aspartate, or lysine, which all have two groups with similar pKa s The presence of nearby charged groups can affect the pKa of an ionizing group For example, the pKa of acetic acid (CH3CO2H) is 46 However, the pKa of the carboxyl group in glycine (+NH3 CH2 CO2H) is 24 The reason lies in the effect of the protonated amino group The positive charge of this group makes it easier to abstract the proton from the carboxylic acid since the negative charge of the carboxylate product is stabilized by having the positive charge of the amino group nearby The effects of nearby charge can be even more dramatic when the ionizable side chain is part of a protein
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pH, pKa, pRoblems
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12 10 8 pH 6 4 2 0
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pKa1 18 pKa2 60 pKa3 92
(18)
HO2C
(92)
NH3 HN NH
(60)
1 2 Equivalents of Base Added
12 10 8 (18) pH 6 4
pKa1 18 HO2C pKa3 97
(97)
2 0 1 2 Equivalents of Base Added 3
12 10 8 (21) pH 6 4 2 0 1 2 Equivalents of Base Added 3
pKa2 pKa1 21 39 HO2C pKa3 98
(98)
NH3 CO2H
(21)
Figure 23-5
Titration of Amino Acids
Multiple ionizable groups titrate separately and in order of increasing pKa
Basic Concepts in Biochemistry
pI ISOELECTRIC POINT
pH pH pH pI means no net charge pI means negative charge pI means positive charge
The pI is a fake little-p function and does not represent the log [I] It represents the pH at which a molecule has no net charge When fully protonated, glycine has a net 1 charge, a charged amino group, and an uncharged, protonated carboxylic acid group About halfway between the titration of the carboxyl and the amino group, the molecule must have no net charge the amount of positive charge on RNH 3 is exactly matched by the amount of negative charge on RCOO If an amino acid (or protein) has more basic groups (Arg, Lys, His) than acidic groups (Glu, Asp), the pI is greater than 7 If an amino acid or protein has more acidic groups, the pI is less than 7 The same considerations apply (but in a more complicated way) to proteins (Fig 23-6)
H2OC
His pl
HN N
H2OC
NH3 24 O2C
NH3 97
Ala pl
Asp pl
H2OC
NH3 21 O2C CO2H
NH3 39 CO2H
NH3 98 CO2
NH2 CO2
Figure 23-6
Figuring out the pI
Average the two pKa s that convert the charge from This will give you an estimate of the pI
1 to 0 and from 0 to
pH, pKa, pRoblems
At the pI, the molecule is neutral [H ] is positively charged, and adding it to another molecule must make that molecule more positively charged As the pH decreases below the pI, the amount of positive charge on the molecule increases (protonating a COO makes the compound more positive, just like protonating an RNH2 group) When the pH is less than the pI, the molecule is positively charged When the pH is greater than the pI, the molecule must be negatively charged
THE BICARBONATE BUFFER
[H ] 24 pCO2/[HCO 3 ]
The CO2 bicarbonate buffer is a little different from buffers using the usual kind of acids and bases, but it is extremely important in maintaining the acid base balance of the blood The acid form of the bicarbonate buffer is actually a gas dissolved in water Dissolved CO2 is turned into an acid by hydration to give H2CO3 Hydrated CO2 is then much like a carboxylic acid It gives up a proton to a base and makes bicarbonate, HCO 3 CO2 H2O H2CO3 H HCO 3
When CO2 is dissolved in water, there is never very much H2CO3, so we can ignore it and count CO2 as the acid and HCO 3 as the base There are two ways of dealing with the bicarbonate buffer system The first uses the Henderson-Hasselbalch equation and an effective pKa of 61 If there is more base (HCO 3 ) than acid (CO2), the pH will always be bigger than the pKa This is usually the case physiologically (pH 74; pKa 61) so that on a molar basis there is always more than 10fold more HCO 3 than CO2 You might be wondering why the bicarbonate buffer can buffer effectively at pH 74 when its pKa is 61 The answer is that it doesn t buffer all that well What makes it unique and the major buffer system of the blood is that CO2, being a gas, can be exhaled by the lungs Exhaling CO2 is equivalent to exhaling protons H+ HCO 3 CO2 H2O
It s not that a proton is exhaled; it s just left behind and turned into water This gives the body control over the concentration of the CO2 by controlling the breathing rate
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