Draw a structure for a peptide that gives Ala, Leu & Val on hydrolysis and fails to react with phenyl isothiocyanate. Mass spectrometry gives a molar mass of 283 for this peptide.Draw the predominant structure at pH 7 using the charge tools to adjust formal charges.You do not have to consider stereochemistry.You do not have to explicitly draw H atoms.• Do not include lone pairs in your answer. They will not be considered in the grading.85کرChemDoodleⓇルنے

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Answered: Draw a structure for a peptide that…

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter22: Proteins

Section: Chapter Questions

Problem 22.99P

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Draw a structure for a peptide that gives Gly, Ile & Phe on hydrolysis and fails to react with phenyl isothiocyanate. Mass spectrometry gives a molar mass of 317 for this peptide. Draw the predominant structure at pH 7 using the charge tools to adjust formal charges.
Draw a structure for a peptide that gives Ala, Leu & Val on hydrolysis and fails to react with phenyl isothiocyanate. Mass spectrometry gives a molar mass of 283 for this peptide. Draw the predominant structure at pH 7 using the charge tools to adjust formal charges.
Match the following amino acids with their chemical properties H -N-CIC- A -A ✓ B но с D VE ✓ F ✓ G / CH3 CH3 CH B H но -N-C-C- feed C но -N-C-C- H CH₂ D HO -N-CIC- 1 H CH₂ OH E но ||| -N-C-C- II H CH₂ I CH₂ CH₂ CH₂ T NH3 I. Acidic II. Nonpolar III. Polar uncharged IV, Basic + F O HO -N-C-C- H CH₂ NH₂ G но | || -N-C-C- I H CH₂ 1
13- If you were to have a mythical AA based on Aspartic acid in which the carboxylate on the side chain is replaced by a hydroxyl (alcoholic) group with pKa of 15.0. What would be the predominant form of this AA at pH 1, 7 and 12? Draw ALL structures with the correct net charges.
(b) Describe how the charge of some amino groups in a protein might differ at pH 9.0 and pH 5.0. the charge on the amino group will differ at pH 5 and pH 9 which will depend on the pKa of the amino acid. (c) Describe how the charge of some carboxyl groups in a protein might differ at pH 9.0 and pH 5.0. charge on carboxyl group will differ at pH 5 and pH 9 which will depend on the pKa of the amino acid. (d) Given your answers to parts (b) and (c), what kind of intramolecular interactions in beta-galactosidase are most likely to be affected by a change in pH from 9.0 to 5.0? (e) Could the interactions you mention in part (d) affect the catalytic activity of beta-galactosidase?
A chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug for the control of gastric acidity and peptic ulcers. Cimetidine reduces gastric acid secretion by inhibiting the interaction of histamine with gastric H2 receptors. In the development of this drug, a cyano group was added to the substituted guanidino group to alter its basicity. Do you expect this modified guanidino group to be more basic or less basic than the guanidino group of arginine? Explain.
Glycine is a diprotic acid, which can potentially undergo two dissociation reactions, one for the a-amino group (-NH3), and the other for the carboxyl (-COOH) group. Therefore, it has two pKą values. The carboxyl group has a pK₁ of 2.34 and the a-amino group has a pK₂ of 9.60. Glycine can exist in fully deprotonated (NH₂-CH₂-COO-), fully protonated (NH3-CH₂-COOH), or zwitterionic form (NH3-CH₂-COO-). Match the pH values with the corresponding form of glycine that would be present in the highest concentration in a solution of th pH. fully deprotonated form NH,−CH,−COO- pH 11.9 pH 6.0 pH 8.0 fully protonated form NH3-CH₂-COOH pH 1.0 Answer Bank pH 7.0 zwitterionic form NH3-CH₂-COO-
For the amino acid alanine, the major species in solution at pH 7 is the zwitterionic form, which has a negatively charged carboxylic acid group and a positively charged amino group. There is a less common neutral form in which neither group is charged. The carboxylic acid group of alanine has a p?apKa of 3.3. The amino group of alanine has a p?apKa of 8.8. Estimate the ratio of the concentration of the neutral amino acid species to the zwitterionic species at pH 7.
Answer the following questions on the basis of the free energies of formation at 25°C shown in the table at the top of the next page: (a) Does the peptide bond between alanine and glycine form spontaneously under standard conditions?
d) Amino acids show both acidic and basic properties. Write equations to illustrate the reactions of 2-amino ethanoic acid with: i) HCI: HOWN ( + Ajouter une légende.. > Statut (Personnalisé)
Draw the product that valine forms when it reacts with di-tert-butyl dicarbonate and triethylamine followed by an aqueous acid wash. O • You do not have to consider stereochemistry. • Do not draw organic or inorganic by-products. • Draw the product in neutral form unless conditions are clearly designed to give an ionic product. • Include cationic counter-ions, e.g., Na+ in your answer, but draw them in their own sketcher. • Do not include anionic counter-ions, e.g., I, in your answer. 90.0 ChemDoodle /n [F
Consider a "tripeptide" with the following features (at pH = 10.8) • The N-terminal amino acid is leucine • The middle amino acid is aspartate • The C-terminal amino acid is lysine i. What is the 1-letter symbol for each of these amino acids il. Calculate the net charge of the predominant ionic state of this tripeptide at pH 10.8. Show work.

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