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Chapter 25: Problem 75

Draw the structures of the dipeptides that can be formed from the reaction between the amino acids glycine and lysine.

Short Answer

Expert verified
The dipeptides are glycyl-lysine and lysyl-glycine.

Step by step solution

01

Understand Amino Acid Structure

First, we need to understand the structure of the amino acids involved. Glycine is the simplest amino acid, with the formula NH2CH2COOH, where the side chain is a hydrogen atom. Lysine has the formula NH2(CH2)4CH(NH2)COOH, with a side chain of (CH2)4NH2, giving it a basic character.
02

Know What Dipeptides Are

A dipeptide is a molecule formed by joining two amino acids. One amino acid contributes an amino group (NH2), and the other contributes a carboxyl group (COOH), forming a peptide bond (CONH) and releasing a molecule of water (H2O).
03

Forming Dipeptide Glycyl-Lysine

In the glycyl-lysine dipeptide, glycine contributes its NH2 group, and lysine contributes its COOH group. Remove a water molecule (by removing an OH from the carboxyl of lysine and an H from the amino of glycine), forming the peptide bond NH2CH2CONH(CH2)4CH(NH2)COOH.
04

Forming Dipeptide Lysyl-Glycine

In the lysyl-glycine dipeptide, lysine contributes its NH2 group, and glycine contributes its COOH group. Remove a water molecule (by removing an OH from the carboxyl of glycine and an H from the amino of lysine), forming the peptide bond NH2(CH2)4CH(NH2)CONHCH2COOH.
05

Verify Structures

Double-check the structures to ensure that each amino acid's side chain and backbone are properly represented. Ensure the peptide bonds (CONH) are formed correctly in both dipeptides.

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Key Concepts

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

Amino Acids
Amino acids are the building blocks of proteins, which play crucial roles in nearly every biological process. They are organic compounds that contain both an amino group (-NH2) and a carboxyl group (-COOH).
This structure allows amino acids to link together, forming proteins or peptides.
There are 20 standard amino acids, each with a unique side chain or R group, which determines its properties and role in the structure and function of proteins.
  • The amino group acts as a base, while the carboxyl group behaves as an acid.
  • They bond together to form peptides, in which sequences can be tailored for specific functions.
  • The sequence and combination of amino acids define the characteristics of the resulting protein or peptide.
Amino acids are essential for life, not only in forming proteins but also in processes such as neurotransmitter transport and biosynthesis.
Glycine
Glycine is the simplest and smallest amino acid, with a side chain consisting of just a hydrogen atom. Its chemical formula is NH2CH2COOH, making it unique among amino acids.
Because of its small size, glycine is highly flexible and can fit into tight spaces within protein structures.
  • Its lack of a complex side chain allows it to contribute minimal steric hindrance.
  • It often appears in protein structures that require tight turns or bends.
  • Glycine plays a crucial role in the formation of proteins like collagen, providing flexibility.
In dipeptides, glycine can easily form bonds with other amino acids due to its simple structure, facilitating the formation of peptide bonds needed for complex protein synthesis.
Lysine
Lysine is a basic amino acid known for its long side chain, which comprises four methylene groups capped with an amino group (NH2). The chemical formula for lysine is NH2(CH2)4CH(NH2)COOH.
This structure imparts lysine with a basic character, enabling it to participate in electrostatic interactions important for protein structure.
  • Lysine's side chain can form ionic bonds due to the presence of the terminal amino group.
  • It is an essential amino acid, meaning it must be ingested through diet as the body cannot synthesize it.
  • Lysine is crucial in protein interactions, where it often facilitates bonding and stabilization.
In forming dipeptides, lysine can provide its amino group for peptide bond formation, contributing to the overall charge balance and structural stability of the resulting molecules.
Peptide Bond
Peptide bonds are the chemical bonds that link amino acids together in proteins and peptides. These bonds are formed through a dehydration synthesis reaction, where a molecule of water is released as a bond is formed between the amino group of one amino acid and the carboxyl group of another.
This bond is represented as (-CONH-), and is critical in maintaining the structure of dipeptides and proteins.
  • The formation of a peptide bond results in a covalent linkage that is strong and stable.
  • As peptide bonds form along a chain of amino acids, they create a backbone that defines the primary structure of proteins.
  • Peptide bonds determine the sequence of amino acids, which further influences the protein's function and stability.
In processes such as those involving glycine and lysine, peptide bonds allow these amino acids to join and form dipeptides like glycyl-lysine or lysyl-glycine, facilitating diverse biological functions.

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Most popular questions from this chapter

What factor determines whether a carbon atom in a compound is chiral?

Fill in the blanks in the given paragraph with the most appropriate term from the following: chiral, cis, constitutional isomers, enantiomers, resonance structures, stereoisomers, trans. Isomers are different compounds that have the same molecular formula. Isomers that have their atoms connected in a different order (branched versus unbranched chain, for example) or a different sequence of bond types \((\mathrm{C}=\mathrm{CCC}\) versus \(\mathrm{CC}=\mathrm{CC},\) for example) are termed Isomers with the same order of connections and sequence of bond types, but which differ in the spatial arrangement of the atoms are called \(.\) This is often seen in compounds where substituents may be on the same or opposite sides of a carbon-carbon double bond. Substituents on the same side are described as \(\quad ;\) those on opposite sides are . A different kind of isomerism characterizes a molecule, that is, a molecule with a structure that allows for two nonsuperimposable mirror-image forms. Two nonsuperimposable mirror images are of the other

Nylon was designed to be a synthetic silk. (a) The average molar mass of a batch of nylon 66 is \(12,000 \mathrm{~g} / \mathrm{mol}\). How many monomer units are there in this sample? (b) Which part of nylon's structure is similar to a polypeptide's structure? (c) How many different tripeptides (made up of three amino acids) can be formed from the amino acids alanine (Ala), glycine (Gly), and serine (Ser), which account for most of the amino acids in silk?

Electrophilic addition of \(\mathrm{HCl}\) to \(\mathrm{cis}-2\) -butene gave 2-chlorobutane, which was determined not to be optically active when examined with a polarimeter. Which of the following is the better explanation for the lack of optical activity in the 2 -chlorobutane formed in this reaction? (a) 2 -Chlorobutane is not chiral. (b) Two enantiomers of 2 -chlorobutane were formed in equal amounts.

Two isomeric alkenes are formed in the dehydration of 2 -methyl-2-butanol. What are these two alkenes? Are they constitutional isomers or stereoisomers?
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