Name: peptide bond formation and shape
Uploaded: 2020-09-24T15:06:53.000Z
Duration: 2 min 43 s
Channel: JoVE

K12 Standards

Pennsylvania State Academic Standards

9-12

Life Science

matter-and-energy-in-organisms-and-ecosystems

Matter and Energy in Organisms and Ecosystems

3.1.9-12.F

Peptide Bonds

Aminozuren binden covalent aan elkaar via peptidebindingen. Een peptidebinding verbindt de carboxylgroep van het ene aminozuur met de aminogroep van het andere. Peptiden zijn kleine ketens van aminozuren die variëren van twee tot vijftig monomeren.Een peptidebinding vormt zich door een condensatiereactie waarbij een watermolecuul vrijkomt. Wanneer een aminogroep en een carboxylgroep aan elkaar binden, resulteert dit in de vorming van een amidegroep. De peptidebinding heeft een stijve vlakke structuur en vertoont enkele kenmerken van een dubbele binding.Dit komt doordat de dubbele binding op de carbonylgroep kan werken als een resonantiestructuur met de koolstof-stikstofpeptidebinding. Deze resonantie leidt tot een afname van de lengte van de enkele binding, een toename van de lengte van de dubbele binding en remt rotatie van de groepen rond de peptidebinding. Peptidebindingen kunnen voorkomen in cis-en trans-conformaties.In de cis-conformatie bevinden de alfa-koolstofatomen zich aan dezelfde kant van de peptidebinding en in de trans-conformatie bevinden ze zich aan weerszijden van de binding. Peptidebindingen komen meestal voor in de trans-conformatie, behalve wanneer proline zijn aminogroep bijdraagt aan de vorming van bindingen. Aminozuren gekoppeld via peptidebindingen hebben een N-terminaal en een C-uiteinde.Het N-uiteinde is het uiteinde waar de aminogroep niet betrokken is bij de vorming van een peptidebinding, en het C-uiteinde is het uiteinde waar de carboxylgroep niet betrokken is bij de vorming van een peptidebinding. De volgorde van aminozuren in een peptide of eiwit begint altijd met het N-uiteinde en eindigt met het C-uiteinde. Wanneer twee aminozuren met elkaar verbonden zijn via een peptidebinding, staan ze bekend als dipeptiden.Wanneer drie en vier aminozuren met elkaar verbonden zijn via peptidebindingen, staan ze bekend als respectievelijk tripeptiden en tetrapeptiden. En wanneer verschillende aminozuren met elkaar verbonden zijn via peptidebindingen, staan ze bekend als polypeptiden. Peptidebindingen kunnen snel worden afgebroken door hydrolyse met behulp van chemische katalysatoren, zoals zuren of enzymen die bekend staan als proteasen.Het verbreken van peptidebindingen omvat de toevoeging van een watermolecuul. Als alternatief kunnen deze bindingen spontaan breken door een langzaam proces in aanwezigheid van water.

peptide-obligaties

Een peptidebinding hecht covalent aminozuren via een dehydratatiereactie. De carboxylgroep van het ene aminozuur en de aminogroep van een ander aminozuur combineren, waardoor een watermolecuul vrijkomt. De resulterende binding is de peptidebinding. De producten die dergelijke bindingen vormen zijn peptiden. Naarmate meer aminozuren zich bij deze groeiende keten voegen, is de resulterende keten een polypeptide. Elk polypeptide heeft aan één uiteinde een vrije aminogroep. Dit uiteinde heeft het N-uiteinde, of het amino-uiteinde, en het andere uiteinde heeft een vrije carboxylgroep: het C- of carboxyluiteinde. Hoewel de termen polypeptide en eiwit soms door elkaar worden gebruikt, is een polypeptide technisch gezien een polymeer van aminozuren, terwijl de term eiwit wordt gebruikt voor een polypeptide of polypeptiden die met elkaar zijn gecombineerd en vaak niet-peptide-prothetische groepen hebben gebonden, een aparte vorm en een unieke functie. Chemie van peptidebindingen Een peptidebinding heeft een stijve vlakke structuur als gevolg van resonantie. Deze resonantie omvat het delen van elektronen tussen de dubbele bindingen die aanwezig zijn in de carbonylgroep en de peptidebinding tussen koolstof en stikstof, die een enkele binding is. Dit resulteert erin dat de lengte van de dubbele binding toeneemt en de lengte van de enkele binding afneemt ten opzichte van de verwachte lengte bij afwezigheid van resonantie. Peptidebindingen kunnen in twee mogelijke conformaties voorkomen: cis en trans. In de cis-configuratie bevinden de alfakoolstoffen van beide aminozuren verbonden door de peptidebinding zich aan dezelfde kant van de binding; en in de trans-configuratie bevinden de alfakoolstoffen van de twee aminozuren verbonden door de peptidebinding zich aan de tegenovergestelde zijden van de binding. De cis-configuratie treedt gewoonlijk op wanneer proline zijn aminogroep bijdraagt aan de vorming van de binding; slechts ongeveer 10% van de prolines wordt echter voorafgegaan door cis-bindingen. Rotatie is niet mogelijk rond peptidebindingen vanwege hun stijve structuur. Er kan echter rotatie optreden rond de bindingen die de alfakoolstof verbinden met respectievelijk de stikstof- en koolstofatomen. Deze tekst is aangepast van <a href="https://openstax.org/books/biology-2e/pages/3-4-proteins">Openstax, Biology 2e, Hoofdstuk 3.4: Eiwitten</a>.

Peptide-obligaties

A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid&#39;s carboxyl group and another amino acid&#39;s amino ...

Education

JoVE Core

Chemistry

Scheikunde

Eén

Biochemistry

Biochemie

KEY TERMS AND CONCEPTS

BELANGRIJKE TERMEN EN CONCEPTEN

peptide bond formation and shape

Peptide bonds join amino acids into peptides and polypeptides. They form when the carboxyl group of one amino acid reacts with the amino group of another. This dehydration reaction releases a water molecule and creates a covalent link.

As more amino acids are added, the chain becomes a polypeptide. Each polypeptide has a free amino group at one end. This end is the N-terminal, or amino-terminal. The other end has a free carboxyl group. This end is the C-terminal, or carboxyl-terminal.

The terms polypeptide and protein are sometimes used as if they mean the same thing. Technically, a polypeptide is a polymer of amino acids. A protein is a polypeptide, or more than one polypeptide, that has joined together and often carries non-peptide prosthetic groups. Proteins also have a distinct shape and a unique function.

Peptide bonds have a rigid, planar shape because of resonance. Resonance is the sharing of electrons between the carbonyl group and the peptide bond between carbon and nitrogen. This changes bond lengths. The double bond becomes longer, and the single bond becomes shorter than expected without resonance.

Peptide bonds can exist in cis and trans forms. In the cis form, the alpha carbons of the two amino acids are on the same side of the bond. In the trans form, they are on opposite sides. The cis form usually appears when proline donates its amino group, but only about 10% of prolines are preceded by cis bonds.

Rotation does not occur around the peptide bond because of its rigid structure. Rotation can still happen around the bonds that connect the alpha carbon to the nitrogen and carbon atoms. This limited movement helps define the shape of peptides and proteins.

Peptide Bond Formation and Shape

functional groups

Functional Groups in Organic Chemistry

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structure of lipids

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chemistry of the cell

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protein and protein structure

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amino acids

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Amino acids are the building blocks of proteins. Each amino acid has the same basic structure. A central carbon atom, called the alpha carbon, is bonded to an amino group, a carboxyl group, and a hydrogen atom. Each amino acid also has an R group, or side chain, attached to the central carbon. The R group is different for every amino acid. It helps determine whether an amino acid is acidic, basic, polar, or nonpolar. Scientists call these molecules amino acids because they contain both amino...

peptide bonds

Peptide bonds join amino acids into peptides and polypeptides. They form when the carboxyl group of one amino acid reacts with the amino group of another. This dehydration reaction releases a water molecule and creates a covalent link. As more amino acids are added, the chain becomes a polypeptide. Each polypeptide has a free amino group at one end. This end is the N-terminal, or amino-terminal. The other end has a free carboxyl group. This end is the C-terminal, or carboxyl-terminal. The...

nucleic acids

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from dna to protein

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key terms and concepts

Learn how peptide bonds form amino acid chains, create N- and C-terminals, and why resonance gives peptides a rigid cis and trans structure.

Peptide Bond Formation and Shape | JoVE K12

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Louisiana Student Standards for Science

High School

Life Sciences

from-molecules-to-organisms-structures-and-processes

From Molecules To Organisms: Structures And Processes

HS-LS1-6

Next Generation Science Standards

From Molecules to Organisms: Structures and Processes

Florida Department of Education

SC.912.L.18

SC.912.L.18.1

SC.912.L.18.4

new-york-state-science-learning-standards

New York State Science Learning Standards

HS-LS1-6.

Light as Energy

The energy required to carry out photosynthesis is light&#8212; typically electromagnetic radiation from the sun. The range of all possible wavelengths is ...

What is Photosynthesis?

All living organisms on Earth are directly or indirectly dependent on photosynthesis. It is the only biological process that can capture energy from ...

The Anatomy of Chloroplasts

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Photosystems

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The Photochemical Reaction Center

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The Antenna Complex

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the-z-scheme-of-electron-transport-in-photosynthesis

The Z-Scheme of Electron Transport in Photosynthesis

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The Calvin Benson Cycle

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Photosynthesis

Autotrophs

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Plant Pigment Chromatography and Floating Leaf Discs in a Vacuum
ExpandOn the day before the experiment, fill a container with water.
Place the spinach ...

Plant Pigment Chromatography
ExpandNOTE: In this experiment you will separate pigments from spinach leaves using chromatography paper. Individual pigments ...

Students who demonstrate understanding can use a model to illustrate how photosynthesis transforms light energy into stored chemical energy.  Assessment Boundary: Assessment does not include specific biochemical steps.

3.1.9-12.E

Compounds Essential to Human Function

The human body is composed of cells that are fundamentally made up of several different molecules. These molecules are essential to carry out all ...

Overview of Functional Groups

Functional groups are a group of atoms with characteristic properties, which when linked to the carbon skeleton of a molecule, alter the properties of ...

Introduction to Carbohydrates

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Sugars as Energy Storage Molecules

What are Lipids?

lipid-derived-compounds-in-the-human-body

Lipid-derived Compounds in the Human Body

Fats and lipids are crucial components in the human body. Some lipid-derived compounds, such as fat-soluble vitamins, eicosanoids, lipoproteins, and ...

What are Proteins?

Protein Organization

Globular Proteins

In organisms, proteins are the most abundant macromolecules. They act as the building blocks of life and play various crucial roles in the body. Proteins ...

Fibrous Proteins

Fibrous proteins are either long and narrow proteins or assemble to form long and thin structures. They contain repetitive units and usually consist of ...

Protein Denaturation

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Role of Proteins in the Human Body

Proteins are the building block of life. They are also&#160; the most abundant macromolecules with as many diverse roles in the body. They are part of ...

Amino acids

Amino acids are the monomers that comprise proteins. Each amino acid has the same fundamental structure, which consists of a central carbon atom, or the ...

Nucleic Acids and Nucleotides

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Nucleic Acid Structure

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What is Energy?

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Energy Budgets and Reproductive Strategies

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Energy Dynamics

The Food Chain
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Production Efficiency

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Trophic Efficiency

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Students who demonstrate understanding can construct and revise an explanation based on evidence for how carbon, hydrogen, and oxygen from sugar molecules may combine with other elements to form amino acids and/or other large carbon-based molecules.  Assessment Boundary: Assessment does not include the details of specific chemical reactions or identification of macromolecules.

Introduction to Cellular Respiration

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What is Glycolysis?

Overview
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Energy-requiring Steps of Glycolysis

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Energy-releasing Steps of Glycolysis

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Outcomes of Glycolysis

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Pyruvate Oxidation

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Mitochondria

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Mitochondrial Membranes

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The Inner Mitochondrial Membrane

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The Citric Acid Cycle: Overview

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The Citric Acid Cycle: Output

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electron-transport-chain-complex-i-and-ii

Electron Transport Chain: Complex I and II

The mitochondrial electron transport chain (ETC) is the main energy generation system in the eukaryotic cells. However, mitochondria also produce ...

electron-transport-chain-complex-iii-and-iv

Electron Transport Chain: Complex III and IV

During the electron transport chain, electrons from NADH and FADH2 are first transferred to complexes I and II, respectively. These two complexes then ...

The Electron Transport Chain

The electron transport chain or oxidative phosphorylation is an exothermic process in which free energy released during electron transfer reactions is ...

the-supercomplexes-in-the-crista-membrane

The Supercomplexes in the Crista Membrane

The mitochondrial cristae membrane is the primary site for the oxidative phosphorylation (OXPHOS) process of energy conversion mediated through ...

ATP Synthase: Structure

ATP synthase or ATPase is among the most conserved proteins found in bacteria, mammals, and plants. This enzyme can catalyze a forward reaction in ...

ATP Synthase: Mechanism

In animals, the mitochondrial F1F0 ATP synthase is the key protein that synthesizes ATP molecules through a complex catalytic mechanism. While the nuclear ...

The ADP/ATP Carrier Protein

ADP/ATP carrier or AAC protein is the most abundant carrier protein in the inner mitochondrial membrane. It transports large quantities of ADP and ATP, ...

Students who demonstrate understanding can use a model to illustrate that cellular respiration is a chemical process whereby the bonds of food molecules and oxygen molecules are broken and the bonds in new compounds are formed resulting in a net transfer of energy.  Assessment Boundary: Assessment should not include identification of the steps or specific processes involved in cellular respiration.

3.1.9-12.G

What is an Ecosystem?

Overview

An ecosystem is the interaction between all abiotic and biotic factors in an environment and can be classified as terrestrial or aquatic. ...

Trophic Levels

All organisms in an ecosystem occupy a trophic level in the food chain. The lowest level consists of primary producers, which synthesize their food from ...

Primary Production

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What are Biogeochemical Cycles?

The most common elements in organic molecules, carbon, hydrogen, oxygen, nitrogen, sulfur, and phosphorus, are only available in the ecosystem in limited ...

The Water Cycle

The Earth&rsquo;s hydrosphere includes all of the areas where the storage and movement of water occurs. Since water is the basis of all living processes, ...

The Carbon Cycle

Carbon is the basis of all organic matter on Earth, and is recycled through the ecosystem in two primary processes: one in which carbon is exchanged among ...

The Nitrogen Cycle

Nitrogen atoms, present in all proteins and DNA, are recycled between abiotic and biotic components of the ecosystem. However, the primary form of ...

The Phosphorus Cycle

Unlike carbon, water, and nitrogen, phosphorus is not present in the atmosphere as a gas. Instead, most phosphorus in the ecosystem exists as compounds, ...

The Sulfur Cycle

Sulfur, an important element in the chemical makeup of proteins, is recycled through the atmosphere and aquatic and terrestrial environments. Found in the ...

Students who demonstrate understanding can use mathematical representations to support claims for the cycling of matter and flow of energy among organisms in an ecosystem.  Assessment Boundary: Assessment is limited to proportional reasoning to describe the cycling of matter and flow of energy.

3.1.9-12.H

Peptide Bond Formation and Shape

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