Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 24, Problem 2PP
Practice Problem 24.2
The guanidino group
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Indicate whether each statement is true or false. (a) Tryptophan is an aromatic amino acid. (b) Lysine is positively charged at pH 7. (c) Asparagine has two amide bonds. (d) Isoleucine and leucine are enantiomers. (e) Valine is probably more water-soluble than arginine.
The amino acid (S)-alanine has the physical characteristics listed under the structure.
How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine?
Another method to form a peptide bond involves a two-step process
Reaction of the p-nitrophenyl ester with an amino acid ester.
Why does a p-nitrophenyl ester “activate” the carboxy group of thefirst amino acid to amide formation?
Chapter 24 Solutions
Organic Chemistry
Ch. 24 - Prob. 1PPCh. 24 - Practice Problem 24.2 The guanidino group NHNHCNH2...Ch. 24 - Prob. 3PPCh. 24 - Prob. 4PPCh. 24 - Prob. 5PPCh. 24 - Prob. 6PPCh. 24 - Prob. 7PPCh. 24 - Practice Problem 24.8
Glutathione is a tripeptide...Ch. 24 - Prob. 9PPCh. 24 - Prob. 10PP
Ch. 24 - Prob. 11PPCh. 24 - Practice Problem 24.12 Show all steps in the...Ch. 24 - Practice Problem 24.13 The synthesis of a...Ch. 24 - Practice Problem 24.14
The terminal carboxyl...Ch. 24 - Prob. 15PPCh. 24 - Prob. 16PPCh. 24 - (a) Which amino acids in Table 24.1 have more than...Ch. 24 - Prob. 18PCh. 24 - 24.19 (a) On the basis of the following sequence...Ch. 24 - Prob. 20PCh. 24 - Prob. 21PCh. 24 - Prob. 22PCh. 24 - Prob. 23PCh. 24 - Prob. 24PCh. 24 - The enzyme lysozyme and its mechanism are...Ch. 24 - Prob. 2LGP
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- What special role does the amino acid cysteine have in the peptides vasopressin and oxytocin?arrow_forwardLysine and tryptophan are two amino acids that contain an additional N atom in the R group bonded to the a carbon. While lysine is classified as a basic amino acid because it contains an additional basic N atom, tryptophan is classified as a neutral amino acid. Explain why this difference in classification occurs.arrow_forwardh) Specify the absolute (R/S) configuration of the amino group in structure IV. (i) If the substituents in structures I, IV and V were identical (all OH or all NH2), which structure would result in a meso compound? (j) If each hydroxy group for structures I, II and VI were replaced with another amino group, which compound would be made optically inactive?arrow_forward
- Explain what is meant by the following :(i) peptide linkage(ii) pyranose structure of glucosearrow_forwardDenaturation of a protein is a physical change, the most readily observable result of which is loss of biological activity. Denaturation stems from changes in secondary, tertiary, and quaternary structure through disruption of noncovalent interactions including hydrogen bonding and hydrophobic interactions. Three common denaturing agents are sodium dodecyl sulfate (SDS), urea, and heat. What kinds of noncovalent interactions might each reagent disrupt?arrow_forwardThe shown image is a reaction diagram for the hydrolysis of peptide bonds. Appropriately substituted phosphonates (structure shown above) were successfully designed as strong inhibitors for proteolytic enzymes. Explain why this strategy was successful. Note that the lengths of P–O bonds in phosphonates are significantly longer than the corresponding C–O bonds.arrow_forward
- The pKaa of the conjugate acid of guanidine is 13.6, making it one of the strongest neutral organic bases. Offer an explanation.arrow_forwardAnother method to form a peptide bond involves a two-step process Conversion of a Boc-protected amino acid to a p-nitrophenyl ester. Why does a p-nitrophenyl ester “activate” the carboxy group of thefirst amino acid to amide formation?arrow_forwardNet Charge on an Amino Group.The amino acid glycine has hydrogen as its side-chain (R) group. Values of pKca= 2:36 and pKaa=9:56 have been previously reported for glycine. Superscripts c, a, and s refer to a-carboxylic acid, α-amino base, and side chain, respectively. Using these values, determine the net charge on the a-amino group of glycine at a physiologic pH of 7.2 and a pH of 3 [70].arrow_forward
- Complete the table for the ionizable groups of the fictitious amino acid hypothetinine. Group alpha-amino alpha-carboxyl Ka 5.24 x 10-⁹ 2.13 x 10-3 pKa (to TWO decimals) 8.9 2.7 Average charge of group when pH=pK (to ONE decimal) -0.5 +0.5arrow_forwardIdentify an amino acid that complies with the following characteristic: (Write the COMPLETE name) A side chain that reacts with HCl via acid-base reactionarrow_forward(b) Which of the following common amino acids has more than one amino group?arrow_forward
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