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Chapter 27: Problem 13

Draw zwitterion forms of these amino acids. (a) Valine (b) Phenylalanine (c) Glutamine

Short Answer

Expert verified
Answer: The zwitterion forms of Valine, Phenylalanine, and Glutamine amino acids are as follows: (a) Valine: H3N+-CH(-CH(CH3)2)-COO- (b) Phenylalanine: H3N+-CH(-CH2-C6H5)-COO- (c) Glutamine: H3N+-CH(-CH2-CH2-CONH2)-COO-

Step by step solution

01

Understand the general structure of an amino acid

An amino acid is composed of a central carbon atom (called the alpha carbon), an amino group (NH2), a carboxyl group (COOH), and a side chain group (R). The general structure of an amino acid is represented as: H2N-CH(R)-COOH Where R is the side chain group. In the zwitterion form, the amino group gains a proton becoming NH3+ while the carboxyl group loses a proton becoming COO-. Hence, it takes the form: H3N+-CH(R)-COO-
02

Know the side chain groups for Valine, Phenylalanine, and Glutamine

The side chain groups (R) for the given amino acids are: (a) Valine: R = -CH(CH3)2 (b) Phenylalanine: R = -CH2-C6H5 (C6H5 is a phenyl group) (c) Glutamine: R = -CH2-CH2-CONH2
03

Draw the zwitterion forms of Valine, Phenylalanine, and Glutamine

Using the general zwitterion structure of an amino acid, substitute the appropriate side chain group for each amino acid: (a) Valine: H3N+-CH(-CH(CH3)2)-COO- (b) Phenylalanine: H3N+-CH(-CH2-C6H5)-COO- (c) Glutamine: H3N+-CH(-CH2-CH2-CONH2)-COO-

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Most popular questions from this chapter

Histamine is synthesized from one of the 20 protein-derived amino acids. Suggest which amino acid is its biochemical precursor and the type of organic reaction(s) involved in its biosynthesis (for example, oxidation, reduction, decarboxylation, nucleophilic substitution).

Draw a structural formula for Lys-Phe-Ala. Label the \(N\)-terminal amino acid and the \(C\)-terminal amino acid. What is the net charge on this tripeptide at \(\mathrm{pH} 6.0\) ?

Describe the behavior of a mixture of glutamic acid, arginine, and valine on paper electrophoresis at pH \(6.0\).

A decapeptide has the following amino acid composition. $$ \mathrm{Ala}_{2} \text {, Arg, Cys, Glu, Gly, Leu, Lys, Phe, Val } $$ Partial hydrolysis yields the following tripeptides. $$ \text { Cys-Glu-Leu + Gly-Arg-Cys + Leu-Ala-Ala + Lys-Val-Phe + Val-Phe-Gly } $$ One round of Edman degradation yields a lysine phenylthiohydantoin. From this information, deduce the primary structure of this decapeptide.

The BOC-protecting group may be added by treatment of an amino acid with di- tert-butyl dicarbonate as shown in the following reaction sequence. Propose a mechanism to account for formation of these products.
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