Draw the Fischer projections representing the L forms of the following amino acids at pH higher than their isoelectric point. a) cysteine b) alanine
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Draw the Fischer projections representing the L forms of the following amino acids at pH higher than their isoelectric point.
a) cysteine
b) alanine
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- To calculate the isoelectric point of amino acids having other ionizable functional groups, we must also take into account the pk, of the additional functional group in the side chain. For an acidic amino acid (one with an additional acidic OH group): For a basic amino acid (one with an aditional basic NH group): pK, (a-COOH) + pK, (second COOH) - pKa (a-NH3") + pK, (side chain NH) pl = a. Indicate which pK, values must be used to calculate the pl of each of the following amino acids: [1] glutamic acid; [2] lysine; [3] arginine. b. In general, how does the pl of an acidic amino acid compare to that of a neutral amino acid? c. In general, how does the pl of a basic amino acid compare to the pl of a neutral amino acid?An oligopeptide has the following amino acid sequence: NH2-Ala-Glu–Leu–Trp–Tyr-Ser–Gly–Lys–Leu-Ala–Arg-Ala-Phe-Ile-Pro–Gly-COOH a) Estimate the net electric charge of the molecule at pH 8.0 and pH 11.0. b) If the above peptide is passed through a cation exchange chromatographic column (that is, the matrix of the column has negative charges) stabilized at pH 8.0, would you expect it to be retained on the column? c) Indicates the number of fragments, and the sequence of each of them, that would be obtained when treating the peptide in question with: i) trypsin, ii) chymotrypsin.(a) A decapeptide has the following amino acid composition: Alaz, Arg, Cys, Glu, Gly, Leu, Lys, Phe, Val Partial hydrolysis yields the following tripeptides: Cys-Glu-Leu + Gly-Arg-Cys + Leu-Ala-Ala+ Lys-Val-Phe + Val-Phe-Gly. Reaction of the decapeptide with 2,4-dinitrofluorobenzene yields 2,4-dinitrophenylysine om the experimental data, deduce the primary structure of the decapeptide.
- The peptide cys-leu-glu-ala-cys-lys is at pH 7 in oxidizing conditions. Part a) Draw the peptide's titration curve. Part b) What would the pI of the peptide be around?Given the following peptides below, what would be more soluble at the indicated pH? 1. (Gly)20 or (Glu)20 in pH 7.0 2. (Lys-Ala)3 or (Phe-Met)3 in pH 7.0 3. (Gly)20 or (Glu)20 in pH 6.0|| 4. (Ala-Ser-Gly)s or (Asn-Ser-His)s in pH 6.0 5. (Ala-Asp-Gly)8 or (Asn-Ser-His)8 in pH 3.0Based on your knowledge of the natural amino acids, what would you expect pKa of the sidechain of beta-(aminomethyl)succinic acid to be? Draw an appropriate titration curve for beta-(aminomethyl)succinic acid, labeling the axes, indicating the equivalence points and the pKavalues, and use a drawing to show the protonated/deprotonated forms.
- Write the one letter code for the oligopeptide Ser-Cys-Ile-Glu-Asn-Cys-Glu and calculate the total charge on it at pH 4.5.Use the pka values, calculate the isoelectric point (pl) of the following amino acids. a) Leucine b) Arginine c) Aspartic acid d) Glutamic acid Amino Acid Alanine Arginine Asparagine Aspartic acid Cysteine Glutamic acid Glutamine Glycine Histidine Isoleucine Leucine Lysine Methionine Phenylalanine Proline Serine Threonine Tryptophan Tyrosine Valine pk, of a-COOH 2.35 2.01 2.02 2.10 2.05 2.10 2.17 2.35 1.77 2.32 2.33 2.18 2.28 2.58 2.00 2.21 2.09 2.38 2.20 2.29 pk of a-NH,* 9.87 9.04 8.80 9.82 10.25 9.47 9.13 9.78 9.18 9.76 9.74 8.95 9.21 9.24 10.60 9.15 9.10 9.39 9.11 9.72 pk of Side Chain 12.48 - 3.86 8.00 4.07 6.10 - 10.53 II 10.07 -a) Circle or highlight with yellow coloring each essential amino acid residue that appears in the hirudin sequence. b) The prototropic groups and their stoichiometry in hirudin are listed below. Calculate the charge on hirudin at pH values 3 and 4 and then estimate its isoionic point.
- A 100 ml solution of 0.1 M amino acid (AA) at ph 1.0 was titrated with NaOH solution. The pH was monitored, and the results were plotted on the graph. The keypoints in the titration are designated I to VII. What is the possible identity of the amino acid? What is the isoelectric point of AA? what is the pKa corresponding to the dissociation of the alpha carboxylic group? Region/point where AA is predominantly present as a (-1) charged species? The effective buffering range for the amino acid in the acidic region? Region/point where the solution has 50:50 percent mixture of the (0) and (-1) speciesYou have isolated the following peptide: His-Ser-Arg-Ala-Glu-Leu-Pro-Gly A) Calculate the approximate charge of this peptide at pH 1, pH 3, pH 5, pH8, pH 11, and pH 14. B) What is the PI of this peptide?For the following amino acids select the INCORRECT alternative: (a) At pH = 4 all migrate towards the cathode except Asp. (b) At pH = 10 all migrate towards the anode. (c) The pI of phenylalanine (Phe) will be about 5.5. (d) The pl of aspartic acid (Asp) will be about 2.8. (e) At pH = 7 the amino acids Arg and Lys migrate towards the cathode and the rest to the anode.