Abstract
The O-N intramolecular acyl migration, also named as an acyl shift or acyl transfer reaction, is well-known in organic and peptide chemistry as a simple rearrangement which proceeds under very mild aqueous conditions. Despite a long history with this reaction, its application in medicinal chemistry has only lately been proposed. In the last decade, this reaction has been intensively studied and several applications of this rearrangement in medicinal chemistry have appeared. O-N Intramolecular acyl migration has been employed in “no auxiliary, no byproduct” prodrug strategies (prodrugs of paclitaxel and other taxoids, prodrugs of HIV protease inhibitors), for the synthesis of peptides containing difficult sequences via “O-acyl isopeptide method”, including Alzheimers disease related amyloid β peptide (Aβ) 1-42, and in the design of pH-, photo- or enzyme-triggered click peptides, as a potential powerful tool for identifying the pathological functions of amyloid β peptides in Alzheimers disease. This review summarized recent advances in the application of O-N intramolecular acyl migration with special focus on medicinal chemistry.
Keywords: O-N Intramolecular acyl migration, O-N intramolecular acyl shift, O-N intramolecular acyl transfer, HIV protease inhibitor prodrugs, paclitaxel prodrugs, O-acyl isopeptide method, depsipeptide, Alzheimer's disease
Current Medicinal Chemistry
Title: Application of the O-N Intramolecular Acyl Migration Reaction in Medicinal Chemistry
Volume: 14 Issue: 26
Author(s): Mariusz Skwarczynski and Yoshiaki Kiso
Affiliation:
Keywords: O-N Intramolecular acyl migration, O-N intramolecular acyl shift, O-N intramolecular acyl transfer, HIV protease inhibitor prodrugs, paclitaxel prodrugs, O-acyl isopeptide method, depsipeptide, Alzheimer's disease
Abstract: The O-N intramolecular acyl migration, also named as an acyl shift or acyl transfer reaction, is well-known in organic and peptide chemistry as a simple rearrangement which proceeds under very mild aqueous conditions. Despite a long history with this reaction, its application in medicinal chemistry has only lately been proposed. In the last decade, this reaction has been intensively studied and several applications of this rearrangement in medicinal chemistry have appeared. O-N Intramolecular acyl migration has been employed in “no auxiliary, no byproduct” prodrug strategies (prodrugs of paclitaxel and other taxoids, prodrugs of HIV protease inhibitors), for the synthesis of peptides containing difficult sequences via “O-acyl isopeptide method”, including Alzheimers disease related amyloid β peptide (Aβ) 1-42, and in the design of pH-, photo- or enzyme-triggered click peptides, as a potential powerful tool for identifying the pathological functions of amyloid β peptides in Alzheimers disease. This review summarized recent advances in the application of O-N intramolecular acyl migration with special focus on medicinal chemistry.
Export Options
About this article
Cite this article as:
Skwarczynski Mariusz and Kiso Yoshiaki, Application of the O-N Intramolecular Acyl Migration Reaction in Medicinal Chemistry, Current Medicinal Chemistry 2007; 14 (26) . https://dx.doi.org/10.2174/092986707782360123
DOI https://dx.doi.org/10.2174/092986707782360123 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
Call for Papers in Thematic Issues
Advances in Medicinal Chemistry: From Cancer to Chronic Diseases.
The broad spectrum of the issue will provide a comprehensive overview of emerging trends, novel therapeutic interventions, and translational insights that impact modern medicine. The primary focus will be diseases of global concern, including cancer, chronic pain, metabolic disorders, and autoimmune conditions, providing a broad overview of the advancements in ...read more
Approaches to the treatment of chronic inflammation
Chronic inflammation is a hallmark of numerous diseases, significantly impacting global health. Although chronic inflammation is a hot topic, not much has been written about approaches to its treatment. This thematic issue aims to showcase the latest advancements in chronic inflammation treatment and foster discussion on future directions in this ...read more
Cellular and Molecular Mechanisms of Non-Infectious Inflammatory Diseases: Focus on Clinical Implications
The Special Issue covers the results of the studies on cellular and molecular mechanisms of non-infectious inflammatory diseases, in particular, autoimmune rheumatic diseases, atherosclerotic cardiovascular disease and other age-related disorders such as type II diabetes, cancer, neurodegenerative disorders, etc. Review and research articles as well as methodology papers that summarize ...read more
Chalcogen-modified nucleic acid analogues
Chalcogen-modified nucleosides, nucleotides and oligonucleotides have been of great interest to scientific research for many years. The replacement of oxygen in the nucleobase, sugar or phosphate backbone by chalcogen atoms (sulfur, selenium, tellurium) gives these biomolecules unique properties resulting from their altered physical and chemical properties. The continuing interest in ...read more
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
CD26: A Multi-Purpose Pharmacological Target
Current Clinical Pharmacology Small Molecule Inhibitors of Peptidylprolyl cis/trans Isomerase
Current Enzyme Inhibition Efficacy and Mechanisms of Action of Lithium Augmentation in Refractory Major Depression
Current Pharmaceutical Design The Potential Role of Morus Alba Leaves Extract on the Brain of Mice Infected with Schistosoma Mansoni
CNS & Neurological Disorders - Drug Targets An Overview of Computer-aided Drug Design Tools and Recent Applications in Designing of Anti-diabetic Agents
Current Drug Targets Rufinamide Improves Functional and Behavioral Deficits <i>via</i> Blockade of Tetrodotoxin-Resistant Sodium Channels in Diabetic Neuropathy
Current Neurovascular Research 5-HT3 Receptors
Current Pharmaceutical Design Revisiting Non-Cancer Drugs for Cancer Therapy
Current Topics in Medicinal Chemistry Effects of Gastrodia Elata Bl on Phencyclidine-Induced Schizophrenia-Like Psychosis in Mice
Current Neuropharmacology Sole Anti-inflammatory Immunomodulators: Innovative Drugs to Prevent and Treat Autoimmune Diseases and Proteopathies
Current Chinese Science Xanthine Oxidoreductase in Drug Metabolism: Beyond a Role as a Detoxifying Enzyme
Current Medicinal Chemistry Cardiovascular Effects of Omega-3 Free Fatty Acids.
Current Vascular Pharmacology Kinase Inhibitors in Multitargeted Cancer Therapy
Current Medicinal Chemistry Studies on the Effect of the Apolipoprotein E Genotype on the Lipid Profile in Alzheimers Disease
Current Alzheimer Research Functional and Structural Benefits Induced by Omega-3 Polyunsaturated Fatty Acids During Aging
Current Neuropharmacology Neurosteroid PREGS Protects Neurite Growth and Survival of Newborn Neurons in the Hippocampal Dentate Gyrus of APPswe/PS1dE9 Mice
Current Alzheimer Research The Glutathione System and its Regulation by Neurohormone Melatonin in the Central Nervous System
Central Nervous System Agents in Medicinal Chemistry Xeno-Cannibalism as an Exacerbation of Self-Cannibalism: A Possible Fruitful Survival Strategy for Cancer Cells
Current Pharmaceutical Design Alternate Strategies of Hsp90 Modulation for the Treatment of Cancer and Other Diseases
Current Topics in Medicinal Chemistry Recent Developments in Group I Metabotropic Glutamate Receptor Allosteric Modulators for the Treatment of Psychiatric and Neurological Disorders (2014-May 2015)
Current Topics in Medicinal Chemistry