EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
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Chapter 24, Problem 24.32SP
Suggest a method for the synthesis of the unnatural D enantiomer of alanine from the readily available I enantiomer of lactic acid.
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3a.
3b.
3c
3d.
3e.
CO₂
clavulanic acid
CH₂-OH
H
Answer the following questions about clavulanic acid.
Does clavulanic acid inhibit D-alanyl-D-alanine transpeptidase?
Does clavulanic acid contain a ß-lactam?
Does clavulanic acid contain a thiazolium ring?
What is the result of the treatment of penicillinase with clavulanic acid?
Does clavulanic acid form a covalent acyl-enzyme intermediate with
penicillinase?
(a) What is the difference between the hormones progesterone and testosterone?
(b) Draw the structure of a a steroid nucleus.
(c) Give the products obtained from complete base hydrolysis in the following reaction:
O
||
CH,−O−C−(CH2)14–CH3
O
CH–0–C−(CH2)14—CH3 + 3 NaOH
O
CH,−0–C−(CH2)14–CH3
α-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?
Chapter 24 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 24.2A - Draw three-dimensional representations of the...Ch. 24.2A - Prob. 24.2PCh. 24.2B - The herbicide glyphosate (Roundup) kills plants by...Ch. 24.4 - Draw the structure of the predominant form of a....Ch. 24.4 - Draw the resonance forms of a protonated guanidino...Ch. 24.4 - Although tryptophan contains a heterocyclic amine,...Ch. 24.4 - Prob. 24.7PCh. 24.4 - Prob. 24.8PCh. 24.5A - Show how the following amino acids might be formed...Ch. 24.5B - Prob. 24.10P
Ch. 24.5C - Prob. 24.11PCh. 24.5C - Show how you would use a Strecker synthesis to...Ch. 24.6 - Suggest how you would separate the free i-ammo...Ch. 24.7A - Propose a mechanism for the acid-catalyzed...Ch. 24.7A - Give equations for the formation and...Ch. 24.7B - Prob. 24.16PCh. 24.7C - Prob. 24.17PCh. 24.8B - Draw the complete structures of the following...Ch. 24.9C - Prob. 24.19PCh. 24.9C - Prob. 24.20PCh. 24.9C - Prob. 24.21PCh. 24.9E - Prob. 24.22PCh. 24.9E - Prob. 24.23PCh. 24.10A - Propose a mechanism for the coupling of acetic...Ch. 24.10B - Show how you would synthesize Leu-Gly-Ala-Val-Phe...Ch. 24.10B - Show how solid-phase peptide synthesis would be...Ch. 24 - a. The isoelectric point (pl) of phenylalanine is...Ch. 24 - Prob. 24.28SPCh. 24 - Prob. 24.29SPCh. 24 - Prob. 24.30SPCh. 24 - Prob. 24.31SPCh. 24 - Suggest a method for the synthesis of the...Ch. 24 - Prob. 24.33SPCh. 24 - Write the complete structures for the following...Ch. 24 - The following structure is drawn in an...Ch. 24 - Prob. 24.36SPCh. 24 - Prob. 24.37SPCh. 24 - Show the steps and intermediates in the synthesis...Ch. 24 - Prob. 24.39SPCh. 24 - Lipoic acid is often found near the active sites...Ch. 24 - Prob. 24.41SPCh. 24 - Prob. 24.42SPCh. 24 - Prob. 24.43SPCh. 24 - Complete hydrolysis of an unknown basic...Ch. 24 - Prob. 24.45SPCh. 24 - Prob. 24.46SPCh. 24 - Prob. 24.47SP
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- 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.arrow_forwardTreating chitin with H2O, -OH hydrolyzes its amide linkages, forming a compound called chitosan. What is the structure of chitosan? Chitosan has been used in shampoos, bers for sutures, and wound dressings.arrow_forwardWhich molecule is the enantiomer of L-alanine, shown below? COOH L-alanine NH CH, COOH NH2 COOH COOH NH2 HOOC HN Molecule D Molecule C Molecule A Molecule Barrow_forward
- i H₂N-CH-C-N-CH-C-N-CH-C-OH CH₂ i CHCH₂ CH₂ H H H + water HCI valine phenylalanine + glycinearrow_forwardCystine is an amino acid formed from the oxidation of twocysteine molecules to form a disulfide bond. The molecular formula of cystine is C6H12O4N2S2. Draw the structural formula of cystine. (arrow_forwardEnzyme-catalyzed decarboxylation of glutamic acid gives 4-aminobutanoic acid . Estimate the pI of 4-aminobutanoic acidarrow_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_forwardO2CCH,CH,-C-CO2 + CH2 NH3 NH3 O2CCH,CH,-C-CO2 + CH2 CH2-C-CO2 + H. phenylalanine -CO2 0,CCH,CH2—CO2 CH2-C-CO2arrow_forwardα-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_forward
- The first step in the catabolism of most amino acids is the removal of the nitrogen atom by transfer to an a-keto acid, a reaction catalyzed by an enzyme called a transaminase. The a-keto acid acceptor is often a-ketoglutarate. Modify the structures in the product to show the products of the transamination of cysteine. Be sure to show functional groups with the charge and number of attached hydrogen atoms appropriate for pH 7.4. transaminase + O=C H₂N-CH + CH₂ CH₂ CH₂ SH Incorrect H₂N || CH | CH₂ | CH₂ I || O || n | CH₂ T SHarrow_forwardIdentify the anomeric carbon. Identify the glycosidic linkage. Lactose ОН ОН OH HO HO, HO OHarrow_forwardFully explain the synthesis of anthocyanins, step by step. Provide pictures.arrow_forward
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