Chapter 29: Q14P (page 1152)
Question: Identify the nucleophile and the electrophile in the following acid–base reactions:
AlCl3is an electrophileand NH3 is a nucleophile.
The H+ of HBr is the electrophile and OH- is the nucleophile.
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Which of the following amino acids are typically found in the interior of a globular protein, and which are typically found on the surface: (a)phenylalanine; (b)aspartic acid; (c) lysine; (d) isoleucine; (e) arginine; (f) glutamic acid?
The 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.
Besides the Boc and Fmoc protecting groups used in peptide synthesis, amines can also be protected by reaction with benzyl chloroformate (). Draw the structure of the product formed by reaction of alanine with benzyl chloroformate
Devise a synthesis of the following dipeptide from amino acid starting materials.
What - halo carbonyl compoundis needed to synthesize each amino acid?
(a) Glycine
(b) Isoleucine
(c) Phenylalanine
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