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Chapter 16: Problem 11

Draw the condensed structural formula for each of the following peptides, and give their three-letter and one-letter abbreviations: a. alanyltryptophan b. glycylthreonine c. serylphenylalanine d. glycylvalylmethionine

Short Answer

Expert verified
a. Ala-Trp (A-W) b. Gly-Thr (G-T) c. Ser-Phe (S-F) d. Gly-Val-Met (G-V-M).

Step by step solution

01

Title - Understand peptide structure

Peptides are chains of amino acids linked by peptide bonds. The condensed structural formula shows the sequence of amino acids in the peptide compactly. Each amino acid abbreviation needs to be understood: Ala (A), Trp (W), Gly (G), Thr (T), Ser (S), Phe (F), Val (V), and Met (M).
02

Title - Draw alanyltryptophan

Alanyltryptophan consists of Alanine followed by Tryptophan. The condensed structural formula is: NH2-CH(CH3)-CO-NH-CH(C8H6N)-COOH. Three-letter abbreviation: Ala-Trp. One-letter abbreviation: A-W.
03

Title - Draw glycylthreonine

Glycylthreonine consists of Glycine followed by Threonine. The condensed structural formula is: NH2-CH2-CO-NH-CH(CH3)(OH)-COOH. Three-letter abbreviation: Gly-Thr. One-letter abbreviation: G-T.
04

Title - Draw serylphenylalanine

Serylphenylalanine consists of Serine followed by Phenylalanine. The condensed structural formula is: NH2-CH(CH2OH)-CO-NH-CH(C6H5)-COOH. Three-letter abbreviation: Ser-Phe. One-letter abbreviation: S-F.
05

Title - Draw glycylvalylmethionine

Glycylvalylmethionine consists of Glycine followed by Valine followed by Methionine. The condensed structural formula is: NH2-CH2-CO-NH-CH(CH3)(CH3)-CO-NH-CH2-CH2-S-CH3-COOH. Three-letter abbreviation: Gly-Val-Met. One-letter abbreviation: G-V-M.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Amino Acid Sequence
Every peptide is composed of a specific sequence of amino acids. These amino acids are linked together by peptide bonds, which create a chain-like structure. Understanding the sequence is important because it determines the peptide's ultimate structure and function. Each amino acid has a unique side chain, which is represented in the condensed structural formula of the peptide. For example, in the peptide alanyltryptophan, alanine and tryptophan are linked together in a specific order to form the peptide. Recognizing and interpreting these sequences allows scientists and students to predict the behavior of peptides in various biological contexts.
Three-letter Abbreviation
To simplify the representation of amino acids in a sequence, a three-letter abbreviation system is often used. Each amino acid has a standardized three-letter abbreviation. For instance, Alanine is abbreviated as 'Ala,' Glycine as 'Gly,' Threonine as 'Thr,' Serine as 'Ser,' Phenylalanine as 'Phe,' and so on. These abbreviations help to quickly identify the components of a peptide sequence without resorting to full structural or chemical names, making it easier to read and comprehend. In the peptide glycylthreonine, 'Gly' represents Glycine and 'Thr' stands for Threonine, clearly indicating the sequence of the peptide.
One-letter Abbreviation
For even greater simplicity, amino acids are also represented using a one-letter abbreviation system. This method assigns a single, unique letter to each amino acid, facilitating rapid communication and notation. For example, Alanine is represented as 'A,' Glycine as 'G,' Threonine as 'T,' Serine as 'S,' Phenylalanine as 'F,' and so on. These one-letter abbreviations are particularly useful in long peptide or protein sequences, where space and clarity are essential. Looking at the peptide serylphenylalanine, 'S' stands for Serine and 'F' stands for Phenylalanine, making the sequence 'S-F,' which is both concise and easy to remember.

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Most popular questions from this chapter

Indicate whether each of the following statements describes primary, secondary, tertiary, or quaternary protein structure: a. Hydrophobic R groups seeking a nonpolar environment move toward the inside of the folded protein. b. Protein chains of collagen form a triple helix. c. An active protein contains four tertiary subunits. d. In sickle-cell anemia, valine replaces glutamate in the \(\beta\) -chain.

In myoglobin, about one-half of the 153 amino acids have nonpolar R groups. a. Where would you expect those amino acids to be located in the tertiary structure? b. Where would you expect the polar \(\mathrm{R}\) groups to be in the tertiary structure? c. Why is myoglobin more soluble in water than silk or wool?

A portion of a polypeptide chain contains the following sequence of amino acids: ( \(\neg\) Met \(\neg\) Leu \(\neg\) Ala \(\neg\) Cys \(\neg\) Asp \(\neg\) ) a. Which amino acid can form a disulfide bond? b. Which amino acids are likely to make the polypeptide more soluble in water? c. Which amino acids are likely to make the polypeptide less soluble in water? d. How does the primary structure of a protein affect its tertiary structure?

Indicate whether each of the following statements describes primary, secondary, tertiary, or quaternary protein structure: a. \(\mathrm{R}\) groups interact to form disulfide bonds or salt bridges. b. Peptide bonds join amino acids in a polypeptide chain. c. Several polypeptides in a beta-pleated sheet are held together by hydrogen bonds between adjacent chains. d. Hydrogen bonding between amino acids in the same polypeptide gives a coiled shape to the protein.

Methanol and ethanol are oxidized by alcohol dehydrogenase. In methanol poisoning, ethanol is given intravenously to prevent the formation of formaldehyde that has toxic effects. a. Draw the condensed structural formulas for methanol and ethanol. b. Would ethanol compete for the active site or bind to a different site? c. Would ethanol be a competitive or noncompetitive inhibitor of alcohol dehydrogenase?
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