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Related Concept Videos

Phosphorylation01:02

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The addition or removal of phosphate groups from proteins is the most common chemical modification that regulates cellular processes. These modifications can affect the structure, activity, stability, and localization of proteins within cells as well as their interactions with other proteins.
During phosphorylation, protein kinases transfer the terminal phosphate group of ATP to specific amino acid side chains of substrate proteins. Serine, threonine, and tyrosine are the most commonly...
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Phosphoinositides are a group of phospholipids containing a glycerol backbone with two fatty acid chains and a phosphate attached to a myoinositol sugar ring. The inositol head group extends into the cytoplasm, where it is modified by adding phosphate groups to form phosphatidylinositol phosphates or PIPs.
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Protein Kinases and Phosphatases02:54

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Proteins undergo chemical modifications that trigger changes in the charge, structure, and conformation of the proteins. Phosphorylation, acetylation, glycosylation, nitrosylation, ubiquitination, lipidation, methylation, and proteolysis are various protein modifications that regulate protein activity. Such modifications are usually enzyme-driven.
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Modified-Release Drug Delivery Systems: Stimuli-Activated01:30

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Stimuli-activated drug delivery systems are designed to release drugs in response to specific physical, chemical, or biological stimuli. These systems often utilize hydrogels—three-dimensional, hydrophilic polymer networks capable of swelling in aqueous environments and retaining significant fluid volumes. Upon exposure to particular stimuli, these hydrogels undergo structural transitions that allow the embedded drug to be released. Due to this adaptive behavior, such systems are also...
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IP3/DAG Signaling Pathway01:11

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Membrane lipids such as phosphatidylinositol (PI) are precursors for several membrane-bound and soluble second messengers. Specific kinases phosphorylate PI and produce phosphorylated inositol phospholipids. One such inositol phospholipids are the  phosphatidylinositol-4,5 bisphosphate [PI(4,5)P2], present in the inner half of the lipid bilayer. Upon ligand binding, GPCR stimulates Gq proteins to turn on phospholipase Cꞵ. Activated phospholipase Cꞵ cleaves PI(4,5)P2 and...
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Phosphodiester Linkages01:01

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Overview
Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
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Chemical Triphosphorylation of Oligonucleotides
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Protease-triggered self-immolative acyl phosphates for controlled phosphate release.

Hunter J Clark1, Yoojeong Chun1, Mark Nitz1

  • 1Department of Chemistry, University of Toronto, Toronto, Ontario, Canada. mark.nitz@utoronto.ca.

Organic & Biomolecular Chemistry
|April 29, 2026
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Summary

Researchers developed a novel protease-responsive scaffold for intracellular phosphate ester delivery. This system triggers phosphate release via enzyme-catalyzed cleavage and intramolecular lactamization, offering a new prodrug strategy.

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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Chemical Biology

Background:

  • Intracellular delivery of phosphate esters is challenging.
  • Prodrug strategies are often required for effective delivery.
  • Existing methods like ProTides have limitations.

Purpose of the Study:

  • To develop a novel scaffold for enzyme-triggered phosphate release.
  • To establish a new mechanistic class of phosphate unmasking.
  • To explore applications in prodrug development and intracellular delivery.

Main Methods:

  • Design and synthesis of a protease-responsive scaffold.
  • Utilizing intramolecular lactamization onto an acyl phosphate.
  • Employing a modified Staudinger ligation for modular synthesis.
  • Testing with a phenylalanine-based monoalkyl acyl phosphate model substrate.

Main Results:

  • Demonstrated chymotrypsin-dependent decomposition of the scaffold.
  • Achieved liberation of phosphate-bearing substrates under mild conditions.
  • Established a distinct mechanistic class of phosphate unmasking.
  • Showcased modular synthesis for generating diverse protease-recognition sequences.

Conclusions:

  • The developed scaffold provides a general platform for enzyme-triggered phosphate release.
  • This approach offers a novel strategy for prodrug development.
  • Potential applications include intracellular probe delivery and therapeutic agent delivery.