Interpretation:
The structure for vasopressin is to be proposed.
Concept introduction:
Vasopressin is a peptide prohormone that regulates the effective osmotic pressure gradient. It comprises
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EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- Both norepinephrine and epinephrine are synthesized from the same protein-derived amino acid. From which amino acid are they synthesized? What types of reactions are involved in their biosynthesis? н он H OH H HO. NH, НО. CH3 (a) (b) HO НО Norepinephrine Epinephrine (Adrenaline)arrow_forwardAfter treatment with peroxyformic acid, the peptide hormone vasopressin is partiallyhydrolyzed. The following fragments are recovered. Propose a structure for vasopressin.Phe@Gln@Asn Pro@Arg@Gly # NH2 Cys@Tyr@PheAsn@Cys@Pro@Arg Tyr@Phe@Gln@Asnarrow_forward18:3c∆9,12,15 all cis-9,12,15-octadecatrienoic, linolenic acid cis-9,12-octadecadienoic, linoleic acid cis-9,12-octadecadienoic, linolenic acid all cis-9,12,15-octadecatrienoic, arachidonic acidarrow_forward
- 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_forwardGive the amino acid sequence of hexapeptides that produce the following sets of fragments upon partial acid hydrolysis: (a) Arg, Gly, Ile, Leu, Pro, Val gives Pro-Leu-Gly, Arg-Pro, Gly-Ile-Val (a) N, L, M, W, V2 gives V-L, V-M-W, W-N-Varrow_forwardb с NH2 O N-methylhexanamide O 2-amino-N,N-diethylbenzamide 2-amino-N-methylbenzamide O N-ethyl-2-hydroxybutanamide 4-aminobenzamide N-ethyl-2-methylbutanamide Submit cyclopentyl acetate ethyl 3-hydroxy-2-methylbutanoate ethyl 3-oxobutanoate cyclopent-3-enyl propanoate ethyl 3-hydroxybutanoate cyclopent-3-enyl acetatearrow_forward
- Although tryptophan contains a heterocyclic amine, it is considered a neutral aminoacid. Explain why the indole nitrogen of tryptophan is more weakly basic than one ofthe imidazole nitrogens of histidine.arrow_forwardVasopressin is a peptide hormone synthesized by the hypothalamus; in its reduced form it has the structure shown. NH2 HS H H H H H *H3N° NH2 N' SH NH2 ОН Vasopressin NH *H2N= NH2 This structure is incorrect in that one of the amino acids is shown in the D-configuration, rather than the L-. Which one is it? What is the amino acid sequence of this peptide? Enter your answer using the single letter abbretiavions for the amino acids; i.e. GPT, not Gly-Pro-Thr. What is the net charge of this peptide at physiological pH? ZI IZ ZI IZ ZIarrow_forwardThe anti-obesity drug orlistat works by irreversibly inhibiting pancreatic lipase, an enzyme responsible for the hydrolysis of triacylglycerols in the intestines, so they are excreted without metabolism. Inhibition occurs by reaction of orlistat with a serine residue of the enzyme, forming a covalently bound, inactive enzyme product. Draw the structure of the product formed during inhibition.arrow_forward
- The addition of a nucleophilic group like a thiol (-SH), or an unprotonated amino group (-NH₂) to an a,ß-unsaturated ketone is important for understanding how NAPQI reacts with glutathione, N-acetylcysteine, or protein amino acid side chains containing -SH or -NH2 groups. In this problem we will add mercaptoethanol to p-benzoquinone. p-Benzoquinone will be a simple model of NAPQI. +H H a single uncharged addition product This reaction will proceed in steps. First the H-S-R will add to the unsaturated ketone to give a charged addition product. Next, a simple proton transfer will form an uncharged adduct in which the 6-membered ring contains one carbonyl and a second enolic hydroxyl. The keto form next will tautomerize to its more stable enol form, and in doing so the 6-membered ring becomes aromatic with 6-π electrons. See page 14 of the lecture notes for Lecture 9 How ADME affects preclinical Drug Design February 24, 2023, where I have shown the mechanism for this addition and give the…arrow_forwardCompounds with polyfunctional groups must follow priority rule. Which of the following compound is correctly named. Justify your claim and construct its correct structure. А: 3-amino-7-carboxy-4-oxoheptanamide 3-amino-7-carbanoyl-4-oxoheptanoic acid 3-amino-4-ox0-7-carbanoylheptanoic acid 3-amino-4-oxo-7-carboxyheptanamide В: С: D:arrow_forwardWhich of the following substituent is an ortho/para-directing activator and an ortho/para-directing deactivator? a amino group b halogen group c nitro group d carboxyl grouparrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning