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Related Concept Videos

SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
Biosynthesis of Nucleic Acids01:28

Biosynthesis of Nucleic Acids

Nucleic acid biosynthesis is a fundamental biochemical process that produces the purine and pyrimidine nucleotides essential for DNA and RNA synthesis. This pathway maintains a balanced nucleotide pool, preventing imbalances that could jeopardize genetic integrity and cellular function. Given the crucial role of nucleotides, their synthesis is tightly regulated to ensure proper cellular homeostasis.Purine BiosynthesisThe biosynthesis of purine nucleotides begins with ribose-5-phosphate, a...
Proofreading01:43

Proofreading

Synthesis of new DNA molecules starts when DNA polymerase links nucleotides together in a sequence that is complementary to the template DNA strand. DNA polymerase has a higher affinity for the correct base to ensure fidelity in DNA replication. The DNA polymerase furthermore proofreads during replication, using an exonuclease domain that cuts off incorrect nucleotides from the nascent DNA strand.Errors during Replication Are Corrected by the DNA Polymerase EnzymeGenomic DNA is synthesized in...
Proofreading01:31

Proofreading

Synthesis of new DNA molecules is carried out by the enzyme DNA polymerase, which adds nucleotides on the daughter strand complementary to the template DNA strand. DNA polymerase has a higher affinity to add the correct base and ensures fidelity during DNA replication. Furthermore,  it exhibits proofreading activity during replication, using an exonuclease domain that cuts off incorrect nucleotides from the nascent DNA strand.
Errors During Replication are Corrected by the DNA Polymerase Enzyme
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

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Related Experiment Video

Updated: Jun 12, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
15:22

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

Published on: April 3, 2014

A stereoelectronic effect in prebiotic nucleotide synthesis.

Amit Choudhary, Kimberli J Kamer, Matthew W Powner

    ACS Chemical Biology
    |May 27, 2010
    PubMed
    Summary

    A proposed mechanism explains how early life

    Area of Science:

    • Origin of Life Studies
    • Prebiotic Chemistry
    • Biochemistry

    Background:

    • The spontaneous synthesis of activated ribonucleotides is crucial for understanding the RNA World hypothesis.
    • Previous research outlined a plausible route for ribonucleotide synthesis.

    Discussion:

    • This study proposes a stereoelectronic effect involving electron delocalization.
    • This n-->pi* interaction explains the regioselective phosphorylation of an anhydroarabinonucleoside.
    • This mechanism operates without the need for protecting groups.

    Key Insights:

    • Electron delocalization between O(5") lone pair and C(2)=N(3) pi* orbital dictates regioselectivity.
    • This interaction facilitates phosphorylation at C(3") over C(5").
    • A stereoelectronic effect may have been pivotal in early RNA synthesis.

    More Related Videos

    Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism
    11:37

    Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism

    Published on: July 28, 2017

    Chemical Triphosphorylation of Oligonucleotides
    13:19

    Chemical Triphosphorylation of Oligonucleotides

    Published on: June 2, 2022

    Related Experiment Videos

    Last Updated: Jun 12, 2026

    Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
    15:22

    Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

    Published on: April 3, 2014

    Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism
    11:37

    Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism

    Published on: July 28, 2017

    Chemical Triphosphorylation of Oligonucleotides
    13:19

    Chemical Triphosphorylation of Oligonucleotides

    Published on: June 2, 2022

    Outlook:

    • This finding provides a chemical basis for the emergence of the RNA World.
    • Understanding such prebiotic chemical pathways is key to abiogenesis research.
    • Further investigation into stereoelectronic effects in prebiotic chemistry is warranted.