Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Amino Acid Catabolism01:18

Amino Acid Catabolism

1
Microorganisms rely on proteins as an essential carbon and energy source, particularly in environments with limited polysaccharides or lipids. However, proteins are too large to cross the plasma membrane unaided, necessitating enzymatic degradation. Microbes secrete extracellular proteases and peptidases that hydrolyze proteins into peptides, which can then be transported across the membrane. Once inside the cell, intracellular proteases degrade these peptides into free amino acids, which...
1
Amino Acid Biosynthetic Pathways01:29

Amino Acid Biosynthetic Pathways

3
Amino acid biosynthesis is essential for cell growth, protein synthesis, and metabolic regulation. Cells generate essential and non-essential amino acids from metabolic intermediates to sustain vital biological functions. These intermediates originate from key metabolic pathways: glycolysis, the tricarboxylic acid (TCA) cycle, and the pentose phosphate pathway. Important precursors include α-ketoglutarate, pyruvate, oxaloacetate, phosphoenolpyruvate, and erythrose-4-phosphate, which...
3
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.4K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.4K
Phase II Reactions: Acetylation Reactions01:24

Phase II Reactions: Acetylation Reactions

188
Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...
188
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

178
Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
178
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

3.1K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
3.1K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Practical access to piperidines.

Nature reviews. Chemistry·2025
Same author

Broad Spectrum Enantioselective Amide Bond Synthetase from <i>Streptoalloteichus hindustanus</i>.

ACS catalysis·2024
Same author

Selective P450<sub>BM3</sub> Hydroxylation of Cyclobutylamine and Bicyclo[1.1.1]pentylamine Derivatives: Underpinning Synthetic Chemistry for Drug Discovery.

Journal of the American Chemical Society·2023
Same author

Two Total Syntheses of Trigoxyphins K and L.

Organic letters·2023
Same author

Selective Hydroxylation of C(sp<sup>3</sup> )-H Bonds in Steroids.

Chemistry (Weinheim an der Bergstrasse, Germany)·2023
Same author

Enzymatic Kinetic Resolution by Addition of Oxygen.

Angewandte Chemie (International ed. in English)·2020

Related Experiment Video

Updated: Jun 7, 2025

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
11:42

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

24.6K

Biocatalytic Amino Acid Functionalisation.

Mark R Petchey1, Pascal Schneider1, Lucy A Harwood1

  • 1Discovery Sciences, BioPharmaceuticals R&D, AstraZeneca, Gothenburg, Sweden.

Chemmedchem
|November 14, 2024
PubMed
Summary
This summary is machine-generated.

Enzymatic synthesis offers a powerful route to novel non-canonical amino acids (ncAAs). This review highlights advancements in enzymatic functionalization for producing diverse ncAAs, crucial for drug discovery.

Keywords:
C−C couplingC−H activationamino acidsbiocatalysispeptides

More Related Videos

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
09:14

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

12.0K
Author Spotlight: In Silico Creation and Impact of Carbonylated Amino Acids on Protein Structure and Function
05:57

Author Spotlight: In Silico Creation and Impact of Carbonylated Amino Acids on Protein Structure and Function

Published on: April 26, 2024

321

Related Experiment Videos

Last Updated: Jun 7, 2025

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
11:42

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

24.6K
Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
09:14

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

12.0K
Author Spotlight: In Silico Creation and Impact of Carbonylated Amino Acids on Protein Structure and Function
05:57

Author Spotlight: In Silico Creation and Impact of Carbonylated Amino Acids on Protein Structure and Function

Published on: April 26, 2024

321

Area of Science:

  • Synthetic chemistry
  • Biotechnology
  • Medicinal chemistry

Background:

  • Advancements in synthetic chemistry are vital for developing new therapeutic modalities.
  • Non-canonical amino acids (ncAAs) offer a way to optimize peptide drug properties beyond standard amino acids.
  • Current synthesis methods for ncAAs include bespoke chemical synthesis or direct modification of parent compounds using chemical reagents or enzymes.

Purpose of the Study:

  • To review recent progress in the enzymatic functionalization of amino acids.
  • To highlight the production of various non-canonical amino acids (ncAAs) using enzymatic methods.
  • To underscore the importance of these advancements for the drug discovery pipeline.

Main Methods:

  • Review of literature on enzymatic functionalization of amino acids.
  • Focus on methods utilizing enzymes for direct modification of amino acids.
  • Exploration of diverse synthetic routes to non-canonical amino acids (ncAAs).

Main Results:

  • Significant advancements have been made in enzymatic approaches for synthesizing non-canonical amino acids (ncAAs).
  • Enzymatic methods provide efficient and specific routes to a wide array of modified amino acids.
  • These methods complement traditional chemical synthesis, expanding the toolkit for medicinal chemists.

Conclusions:

  • Enzymatic functionalization represents a key innovation in producing non-canonical amino acids (ncAAs).
  • The development of these synthetic strategies is crucial for the advancement of peptide-based therapeutics.
  • Continued research in enzymatic synthesis will accelerate the drug discovery process by providing novel molecular building blocks.