Package: Loose Leaf Organic Chemistry with Connect 2-year Access Card
5th Edition
ISBN: 9781259729980
Author: SMITH
Publisher: MCG
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Chapter 29, Problem 29.54P
Interpretation Introduction
Interpretation: The structures of the amino acids that form gramicidin S is to be drawn and. The reason corresponding to the fact that the given compound possesses two unusual structural features are to be explained.
Concept introduction: Peptide linkage is formed between the amino group of one amino acid and the carboxyl group of other amino acid with the loss of water molecule. Amino acids are naturally occurring compounds in which the amino group is present on the alpha carbon of carboxyl group. The name of amino acids is represented by the one-letter and three-letter abbreviations.
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Gramicidin S, a topical antibiotic produced by the bacterium Bacillus brevis, is a cyclic decapeptide formed from five amino acids. Draw the structures of the amino acids that form gramicidin S, and explain why this compound possesses two unusual structural features.
Cholic acid is secreted in bile as an amide linked to the aminogroup of glycine. This cholic acid–amino acid combination acts asan emulsifying agent to disperse lipids in the intestines for easierdigestion. Draw the structure of the cholic acid–glycine combination,and explain why it is a good emulsifying agent.
Glutathione, a powerful antioxidant that destroys harmful oxidizing agents in cells, is composed of glutamic acid, cysteine, and glycine, and has the following structure:
a. What product is formed when glutathione reacts with an oxidizing agent?
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Chapter 29 Solutions
Package: Loose Leaf Organic Chemistry with Connect 2-year Access Card
Ch. 29 - Prob. 29.1PCh. 29 - Problem 29.2
What form exists at the isoelectric...Ch. 29 - Problem 29.3
Explain why the of the group of an...Ch. 29 - Prob. 29.4PCh. 29 - Problem 29.5
What -halo carbonyl compound is...Ch. 29 - Problem 29.6
The enolate derived from diethyl...Ch. 29 - Problem 29.7
What amino acid is formed when is...Ch. 29 - Problem 29.8
What aldehyde is needed to synthesize...Ch. 29 - Problem 29.9
Draw the products of each...Ch. 29 - Prob. 29.10P
Ch. 29 - Prob. 29.11PCh. 29 - Prob. 29.12PCh. 29 - Problem 29.13
What alkene is needed to synthesize...Ch. 29 - Problem 29.14
Draw the structure of each peptide....Ch. 29 - Problem 29.15
Name each peptide using both the...Ch. 29 - Prob. 29.16PCh. 29 - Prob. 29.17PCh. 29 - Problem 29.18
Glutathione, a powerful antioxidant...Ch. 29 - Problem 29.19
Draw the structure of the...Ch. 29 - Problem 29.20
Give the amino acid sequence of an...Ch. 29 - a What products are formed when each peptide is...Ch. 29 - Prob. 29.22PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.25PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.28PCh. 29 - Draw the product formed when the following amino...Ch. 29 - With reference to the following peptide: a...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.32PCh. 29 - Histidine is classified as a basic amino acid...Ch. 29 - Tryptophan is not classified as a basic amino acid...Ch. 29 - What is the structure of each amino acid at its...Ch. 29 - What is the predominant form of each of the...Ch. 29 - 29.37 What is the predominant form of each of the...Ch. 29 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 29 - 29.39 Draw the organic products formed in each...Ch. 29 - 29.40 What alkyl halide is needed to synthesize...Ch. 29 - 29.41 Devise a synthesis of threonine from diethyl...Ch. 29 - 29.42 Devise a synthesis of each amino acid from...Ch. 29 - Prob. 29.43PCh. 29 - Prob. 29.44PCh. 29 - Prob. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.49PCh. 29 - Prob. 29.50PCh. 29 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 29 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr:
a....Ch. 29 - Prob. 29.53PCh. 29 - Prob. 29.54PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.56PCh. 29 - Prob. 29.57PCh. 29 - Prob. 29.58PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - 29.60 Draw the organic products formed in each...Ch. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.63 Besides the Boc and Fmoc protecting groups...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - 29.65 Draw the mechanism for the reaction that...Ch. 29 - 29.66 Which of the following amino acids are...Ch. 29 - 29.67 After the peptide chain of collagen has been...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.71P
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- Compare the structures of the peptide neurotransmitters Met-enkephalin and Leu-enkephalin in terms of a. what they have in common. b. how they differ.arrow_forwardAt room temperature, amino acids are solids with relatively high decomposition points. Explain why.arrow_forwardGlutathione, a powerful antioxidant that destroys harmful oxidizing agents in cells, is composed of glutamic acid, cysteine, and glycine, and has the following structure:a. What product is formed when glutathione reacts with an oxidizing agent? b. What is unusual about the peptide bond between glutamic acid and cysteine?arrow_forward
- α-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. Draw the structures of the two intermediates formed in this reaction.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_forwardThe first amino acid incorporated into a polypeptide chain during its biosynthesis in prokaryotes is N-formylmethionine. Explain the purpose of the formyl grouparrow_forward
- The dynorphins are a group of opioid peptides that play an importantrole in changes in the brain associated with cocaine addiction. One ofthese peptides, dynorphin A, contains the following amino acidsequence: Tyr–Gly–Gly–Phe–Leu–Arg–Arg–Ile–Arg–Pro–Lys–Leu–Lys.Draw the amino acids and peptide fragments formed when dynorphin A is treated with each reagent or enzyme: (a) chymotrypsin; (b) trypsin; (c)carboxypeptidase; (d) C6H5N=C=S.arrow_forwardWhat type of bond is broken when peptides undergo hydrolysis?arrow_forward1. What is the active form (structure) of doxorubicin *write the structure legiblyarrow_forward
- Draw the structure formed between alpha-L-erythose with amino acid asparagine and label the type of bond that is formed.arrow_forwardα-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. What amino acid is formed when the aldehyde that is used is 3-methylbutanal?arrow_forward1a. Describe the formation of a bond between two amino acids that craves a peptide. 1B. The image below is a dipeptide. How can you always identified the peptide bond between amino acids?arrow_forward
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