Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 29, Problem 29.44P
Devise a synthesis of each amino acid from acetaldehyde (
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2.
Classify the following amino acids as nonpolar, polar basic, polar acidic, or polar neutral.
(a)
(b)
(c)
(d)
H₂N-CH-COH
CH-OH
I
CH3
||
H₂N-CH-C-OH
I
CH₂
C=O
1
OH
H₂N-CH-C-OH
CH₂
T
CH-CH3
CH₂
H₂N-CH-C-OH
ī
CH₂
OH
229
write the IUPAC names for the following
aminos
CH,CH,
CH;CH,NH2
b)
CH;CH,
c)
CH
9. Escriha la aetunt -.
(a) What amino acids would be obtained by hydrolysis of
the following tripeptide?
H,NCHCNHCHCNHCHCOH
(CH)2CH H.CоН Н-ССH-СОН
(b) How many different tripeptides can be made from gly-
cine, serine, and glutamic acid? Give the abbreviation for
each of these tripeptides, using the three-letter codes and
one-letter codes for the amino acids.
Chapter 29 Solutions
Organic Chemistry
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 - 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 - Prob. 29.8PCh. 29 - Prob. 29.9PCh. 29 - Prob. 29.10P
Ch. 29 - Prob. 29.11PCh. 29 - Problem 29.13
What alkene is needed to synthesize...Ch. 29 - Problem 29.14
Draw the structure of each peptide....Ch. 29 - Name each peptide using both the one-letter and...Ch. 29 - Prob. 29.15PCh. 29 - Prob. 29.16PCh. 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. 29.21PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.24PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.27PCh. 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. 29.31PCh. 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 - To calculate the isoelectric point of amino acids...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 - Draw the organic product formed when the amino...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. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - Prob. 29.48PCh. 29 - Prob. 29.49PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.51PCh. 29 - Prob. 29.52PCh. 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. 29.55PCh. 29 - Explain why a peptide CN bond is stronger than an...Ch. 29 - Prob. 29.57PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.59PCh. 29 - Prob. 29.60PCh. 29 - Prob. 29.61PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - Prob. 29.63PCh. 29 - Prob. 29.64PCh. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - Which of the following amino acids are typically...Ch. 29 - After the peptide chain of collagen has been...Ch. 29 - Prob. 29.72PCh. 29 - Prob. 29.73PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.75P
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- Draw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu. (The structure of a related peptide, met-enkephalin, appeared in Section 22.6B.)arrow_forwardAlanine is one of the 20 amino acids (it contains both an amino and a carboxyl group) found in proteins - \, Is alanine better represented by structural formula A or B? Explain. CH-CH-Ö-OH CH-CH-Ö-o- NH, NH3" (A) (B)arrow_forwardFf.289.arrow_forward
- Draw the structure of (a) a ketotetrose; (b) an aldopentose; (c) an aldotetrose.arrow_forwardA 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.arrow_forward22-47 How many different tetrapeptides can be made (a) if the peptides contain the residues of asparagine, proline, serine, and metbionine and (b) if all 20 amino acids can be used?arrow_forward
- 27. Which of the following statements about cholesterol is not correct? CH3 CH3 H. d но Cholesterol (a) Cholesterol is a steroid that contains a tetracyclic ring system. (b) Cholesterol is a steroid that contains 8 chiral carbons and can form 28 or 256 stereoisomers. (c) Each atom or group attached to a ring-junction carbon (i.e., carbons a -e) is in a trans or axial position. Because of this the tetracyclic ring system is mostly flat. (d) Cholesterol is used to synthesized vitamin D, bile acids, sex hormones, and adrenocorticoid hormones. (e) Cholesterol is not found in the cell membranes of animals.arrow_forwardIndicate whether each statement is true or false. (a) Thesequence of amino acids in a protein, from the amine endto the acid end, is called the primary structure of the protein.(b) Alpha helix and beta sheet structures are examplesof quaternary protein structure. (c) It is impossiblefor more than one protein to bind to another and make ahigher order structure.arrow_forwardSome of the most important organic compounds in biochemistry are the α-amino acids, represented by the general formula shown.Write structural formulas for the following α-amino acids.(a) Alanine (R = methyl)(b) Valine (R = isopropyl)(c) Leucine (R = isobutyl)(d) Isoleucine (R = sec-butyl)(e) Serine (R = XCH2, where X is the functional group that characterizes alcohols)(f) Cysteine (R = XCH2, where X is the functional group that characterizes thiols)(g) Aspartic acid (R = XCH2, where X is the functional group that characterizes carboxylic acids)arrow_forward
- Please give a clear explanation handwritten answer..arrow_forwardGive the amino acid sequence of a hexapeptide that contains the amino acids Ala, Val, Ser, Ile, Gly, Tyr, and forms the following fragments when partially hydrolyzed with HCl: Gly–Ile–Val, Ala–Ser–Gly, and Tyr–Ala.arrow_forward8.) Which of these a-amino acids is described by the IUPAC name 2-amino-3-(4-hydroxyphenyl)propanoic acid? (Hint: draw it.) D) glutamine A) alanine B) phenylalanine C) proline E) tyrosine F) tryptophan G) threoninearrow_forward
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