Answer the following question based on the catalytic mechanism of chymotrypsin. Its catalytic triad and substrate are shown below: R2: R1 H-N What is the role of the amide carbonyl in this mechanism (one word answer)?
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Is this a base or a nucleophile
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- Provide an electron pushing mechanism for the conversion shown below. Abbreviate the enzyme catalyst active site groups (BH* and B:) as needed. Which purine base is used? NH₂ Enz H₂O 'N NH3a. 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?Several compounds have been found to inhibit -lactamase, and drugs based on these compounds can be taken in combination with penicillins and cephalosporins to restore their effectiveness when resistance is known to be a problem. The commonly prescribed formulation called Augmentin is a combination of the -lactamase inhibitor shown below with amoxicillin (shown above). It is used to treat childhood ear infections when resistance is suspected, and many kids know it as the white liquid that tastes like bananas. Which of the statements below are true statements? 1. The stereochemistry of the fusion between the four-and five-membered rings in the inhibitor and amoxicillin are different. 2. The inhibitor possesses enol ether and allylic alcohol functional groups while the antibiotic possesses a phenol and a secondary amide functional group. 3. Neither the inhibitor nor the antibiotic contains strained rings. 4. Both 1 and 2 are true.
- a) Draw the curly arrow mechanism to show a proton transfer between benzoic acid and the salt sodium ethoxide (C₂H, ONA): b) Amino acids can exist in two possible forms (shown) i) Explain the position of the following equilibrium: OH R NH₂ H R NH3 H ii) Predict, giving reasons, the melting point of amino acids compared to other similar mass hydrogen bonded organics such as amines and diols.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…Which of the following substituent is an ortho/para-directing deactivator? a amino group b halogen group c phenyl group d carboxyl group
- A) Imine and Enamine Formation CH3 N-N S. B) Imine Formation (Ignore chiral centers) RacemicWhich of the following substituent is a meta-directing deactivator? a amino group b halogenation group c phenyl group d carboxyl groupUnder acidic conditions (such as in your stomach) benzyl penicillin (BP) breaks down to three products which we will call A, B, and C in a parallel reaction with the following A BP B. values for the rate constants: ka = 7.0 × 10-4 sec-1; ks = 4.1 x 10-3 sec-1; and ke 5.7 x 10-3 sec-1. What is the yield of product A? In other words, after the reaction has reached completion what fraction of the product is present as compound-A?
- When aspirin is made from acetic acid, the by product is H2O; when acetic anhydride 1Sused, the by-product is acetic acid. When acetyl chloride is used (see above), the by product is HC1. Which route should you use if you were working for Leica, a company that mass produces aspirin on a daily basis? Why?(a) Provide (Draw) products for the following reactions OH OH 1. PCC 2. t-BuPh₂SiCl DMAP,CH₂Cl2The conversion of methionine to homocysteine requires folate (N5-methyl THF) while the remethylation of homocysteine to methionine requires Vitamin B12. Describe at least two different ways in which these enzymatic reactions could be positively influenced to help reduce this individual's homocysteine levels.