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 29.22P
Interpretation Introduction
Interpretation: The sequence of heptapeptide that contains amino acids Ala, Arg, Glu, Gly, Leu, Phe and Ser from the given experimental data is to be predicted.
Concept introduction: The chemical compounds in which carbon atom is bonded to
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Deduce the sequence of a heptapeptide that contains the amino acids Ala, Arg, Glu, Gly, Leu, Phe, and Ser, from the following experimental data. Edman degradation cleaves Leu from the heptapeptide, and carboxypeptidase forms Glu and a hexapeptide. Treatment of the heptapeptide with chymotrypsin forms a hexapeptide and a single amino acid. Treatment of the heptapeptide with trypsin forms a pentapeptide and a dipeptide. Partial hydrolysis forms Glu, Leu, Phe, and the tripeptides Gly–Ala–Ser and Ala–Ser–Arg.
Deduce the sequence of a pentapeptide that contains the amino acids Ala, Glu, Gly, Ser, and Tyr, from the following experimental data. Edman degradation cleaves Gly from the pentapeptide, and carboxypeptidase forms Ala and a tetrapeptide. Treatment of the pentapeptide with chymotrypsin forms a dipeptide and a tripeptide. Partial hydrolysis forms Gly, Ser, and the tripeptide Tyr–Glu–Ala.
Somatostatin is a tetradecapeptide of the hypothalamus that inhibits the release of pituitary growth hormone. Its amino acid sequence has been determined by a combination of Edman degradations and enzymic hydrolysis experiments. On the basis of the following data, deduce the primary structure of somatostatin: 1. Edman degradation gave PTH-Ala. 2. Selective hydrolysis gave peptides having the following indicated sequences: Phe-Trp Thr-Ser-Cys Lys-Thr-Phe Thr-Phe-Thr-Ser-Cys Asn-Phe-Phe-Trp-Lys Ala-Gly-Cys-Lys-Asn-Phe 3. Somatostatin has a disulfide bridge.
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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