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Related Concept Videos

Base-Catalyzed Aldol Addition Reaction01:08

Base-Catalyzed Aldol Addition Reaction

3.5K
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
3.5K
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

2.3K
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
2.3K
Intramolecular Aldol Reaction01:18

Intramolecular Aldol Reaction

2.7K
Intramolecular aldol reaction occurs in dicarbonyl compounds such as dialdehydes, diketones, and keto-aldehydes. The dicarbonyl compounds possess more than one nucleophilic ⍺ carbon for the base to deprotonate and form the enolates. For example, in symmetrical diketones, there are four ⍺ carbons. Hence, four types of enolates are possible when treated with a base. However, since the molecule is symmetrical, the enolates formed on either side of one carbonyl group are equivalent to...
2.7K
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation01:14

Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation

6.0K
This lesson delves into the aldol condensation catalyzed by bases, where aldols undergo dehydration to enals. As shown in Figure 1, the β-hydroxy aldehyde formed in a base-catalyzed aldol addition reaction dehydrates on heating to yield an unsaturated carbonyl product, which is commonly referred to as an enal.
6.0K
Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

5.4K
Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
5.4K
Aldol Condensation vs Claisen Condensation01:33

Aldol Condensation vs Claisen Condensation

7.0K
Aldol condensation is an acid or base-catalyzed condensation between aldehydes or ketones to give an α,ꞵ-unsaturated carbonyl compound. A base-promoted condensation between ester molecules to produce a ꞵ-ketoester is known as the Claisen condensation. In the presence of a base, both reactions involve deprotonation of the acidic α hydrogen to produce the corresponding enolates. The nucleophilic enolates attack their respective nonenolized carbonyl compound forming a...
7.0K

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Updated: Apr 30, 2026

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

Sarah E Franz1, Jon D Stewart1

  • 1Department of Chemistry, University of Florida, Gainesville, Florida, USA.

Advances in Applied Microbiology
|April 29, 2014
PubMed
Summary
This summary is machine-generated.

Threonine aldolases are enzymes that form carbon-carbon bonds using glycine and aldehydes. This review covers their reaction mechanisms, synthetic applications, and recent crystallographic and protein engineering studies.

Keywords:
Aldol reactionAldolaseAmino acidsCarbon–carbon bond formationPyridoxal phosphateThreonine

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Area of Science:

  • Biocatalysis
  • Enzyme engineering
  • Organic synthesis

Background:

  • Threonine aldolases are pyridoxal phosphate-dependent enzymes catalyzing the condensation of amino acids and aldehydes.
  • These enzymes form two adjacent chiral centers, exhibiting high stereoselectivity at the α-carbon but moderate selectivity at the β-carbon.
  • They accept diverse aldehydes, making them valuable tools in synthetic chemistry.

Purpose of the Study:

  • To review the reaction mechanism of threonine aldolases.
  • To compile published synthetic reactions utilizing threonine aldolases up to early 2014.
  • To present the current status of crystallographic and protein engineering studies on these enzymes.

Main Methods:

  • Literature review of threonine aldolase reactions and studies.
  • Summary of enzymatic reaction mechanisms.
  • Compilation of crystallographic and protein engineering data.

Main Results:

  • Threonine aldolases demonstrate high α-carbon stereoselectivity and broad substrate acceptance for aldehydes.
  • A comprehensive list of synthetic applications up to early 2014 is provided.
  • Current advancements in structural and engineering studies are highlighted.

Conclusions:

  • Threonine aldolases are versatile biocatalysts with significant potential in synthetic organic chemistry.
  • Further research in protein engineering and structural biology can enhance their catalytic efficiency and selectivity.
  • These enzymes represent a key component of the modern synthetic chemist's toolkit.