Abstract
In recent years, peptidomimetics have gained enormous importance in drug design aiming to achieve increased drug metabolic stability and higher selectivity. In the field of peptidomimetics, β-peptides incorporating β2- and β3-amino acids (the higher homologs of natural α-amino acids) provide a powerful method for the synthesis of peptidomimetics with particular secondary structures. In this regard, 1,2,3-triazole-modified peptidomimetics can act as effective peptide surrogates, and therefore have gained considerable attention. In the present report, 1,4-disubstituted 1,2,3-triazoles attached to β-amino acids were prepared selectively from the corresponding alkynyl-β2-amino acids according to Huisgen’s copper-catalyzed 1,3-dipolar cycloaddition (CuAAC), under mild conditions and with very high efficiency. Different azide derivatives, including some incorporating α-amino acids, were employed in this cycloaddition reaction. The enantiopure compounds were obtained via diastereomeric salt formation with chiral adjuvants, and subsequent separation.
Keywords: Triazol, click-reaction, β-amino acids, peptidomimetics, enantio- and diastereoseparation.
Current Topics in Medicinal Chemistry
Title:Enantiopure 1,2,3-Triazolyl-β-amino Acids via Click Cycloaddition Reaction on Racemic Alkynyl Precursors Followed by Separation of Stereoisomers
Volume: 14 Issue: 10
Author(s): Margarita Escudero-Casao, Alberto Vega-Penaloza and Eusebio Juaristi
Affiliation:
Keywords: Triazol, click-reaction, β-amino acids, peptidomimetics, enantio- and diastereoseparation.
Abstract: In recent years, peptidomimetics have gained enormous importance in drug design aiming to achieve increased drug metabolic stability and higher selectivity. In the field of peptidomimetics, β-peptides incorporating β2- and β3-amino acids (the higher homologs of natural α-amino acids) provide a powerful method for the synthesis of peptidomimetics with particular secondary structures. In this regard, 1,2,3-triazole-modified peptidomimetics can act as effective peptide surrogates, and therefore have gained considerable attention. In the present report, 1,4-disubstituted 1,2,3-triazoles attached to β-amino acids were prepared selectively from the corresponding alkynyl-β2-amino acids according to Huisgen’s copper-catalyzed 1,3-dipolar cycloaddition (CuAAC), under mild conditions and with very high efficiency. Different azide derivatives, including some incorporating α-amino acids, were employed in this cycloaddition reaction. The enantiopure compounds were obtained via diastereomeric salt formation with chiral adjuvants, and subsequent separation.
Export Options
About this article
Cite this article as:
Escudero-Casao Margarita, Vega-Penaloza Alberto and Juaristi Eusebio, Enantiopure 1,2,3-Triazolyl-β-amino Acids via Click Cycloaddition Reaction on Racemic Alkynyl Precursors Followed by Separation of Stereoisomers, Current Topics in Medicinal Chemistry 2014; 14 (10) . https://dx.doi.org/10.2174/1568026614666140423110420
DOI https://dx.doi.org/10.2174/1568026614666140423110420 |
Print ISSN 1568-0266 |
Publisher Name Bentham Science Publisher |
Online ISSN 1873-4294 |
Call for Papers in Thematic Issues
Chemistry Based on Natural Products for Therapeutic Purposes
The development of new pharmaceuticals for a wide range of medical conditions has long relied on the identification of promising natural products (NPs). There are over sixty percent of cancer, infectious illness, and CNS disease medications that include an NP pharmacophore, according to the Food and Drug Administration. Since NP ...read more
Current Trends in Drug Discovery Based on Artificial Intelligence and Computer-Aided Drug Design
Drug development discovery has faced several challenges over the years. In fact, the evolution of classical approaches to modern methods using computational methods, or Computer-Aided Drug Design (CADD), has shown promising and essential results in any drug discovery campaign. Among these methods, molecular docking is one of the most notable ...read more
Drug Discovery in the Age of Artificial Intelligence
In the age of artificial intelligence (AI), we have witnessed a significant boom in AI techniques for drug discovery. AI techniques are increasingly integrated and accelerating the drug discovery process. These developments have not only attracted the attention of academia and industry but also raised important questions regarding the selection ...read more
From Biodiversity to Chemical Diversity: Focus of Flavonoids
Flavonoids are the largest group of polyphenols, plant secondary metabolites arising from the essential aromatic amino acid phenylalanine (or more rarely from tyrosine) via the phenylpropanoid pathway. The flavan nucleus is the basic 15-carbon skeleton of flavonoids (C6-C3-C6), which consists of two phenyl rings (A and B) and a heterocyclic ...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
-
Ion Channels and Epilepsy
Current Pharmaceutical Design Expanding Spectrum of Sodium Potassium Chloride Co-transporters in the Pathophysiology of Diseases
Current Neuropharmacology Metabolic Basis of Sporadic Alzeimer’s Disease. Role of Hormones Related to Energy Metabolism
Current Pharmaceutical Design Dreams and Psychedelics: Neurophenomenological Comparison and Therapeutic Implications
Current Neuropharmacology A Focus on Pharmacological Management of Catecholaminergic Polymorphic Ventricular Tachycardia
Mini-Reviews in Medicinal Chemistry Melatonin, its Metabolites and its Synthetic Analogs as Multi-Faceted Compounds: Antioxidant, Prooxidant and Inhibitor of Bioactivation Reactions
Current Medicinal Chemistry Pharmacological Treatment of Diabetic Peripheral Neuropathy: An Update
CNS & Neurological Disorders - Drug Targets Huntingtons Disease: The Value of Transcranial Meganetic Stimulation
Current Medicinal Chemistry Medications Acting on the GABA System in the Treatment of Alcoholic Patients
Current Pharmaceutical Design Opinion Paper: Post-surgical Delirium, Consciousness, and Therapy
Recent Patents on CNS Drug Discovery (Discontinued) Electrochemical Sensors in the Development of Selective Methods for Antiepileptic Drugs Determination
Combinatorial Chemistry & High Throughput Screening The Use of Antibody Engineering to Create Novel Drugs that Target N-methyl-D-Aspartate Receptors
Current Drug Targets Therapeutic Potential of Agonists and Antagonists of A1, A2a, A2b and A3 Adenosine Receptors
Current Pharmaceutical Design Pharmacological Investigation and Unraveling Mechanism of Action of Jasminum sambac Flowers for Predicated Treatment of Alzheimer’s Disease
Current Nutrition & Food Science Increased Neuronal Injury in Clock Gene Per-1 Deficient-Mice after Cerebral Ischemia
Current Neurovascular Research Astroglial Connexins in Neurological and Neuropsychological Disorders and Radiation Exposure
Current Medicinal Chemistry Why Anticancer Nanomedicine Needs Sugars?
Current Medicinal Chemistry Cerebroprotective Functions of HO-2
Current Pharmaceutical Design Protein Kinases and their Modulation in the Central Nervous System
Current Medicinal Chemistry - Central Nervous System Agents Purines and Pyrimidines: Metabolism, Function and Potential as Therapeutic Options in Neurodegenerative Diseases
Current Protein & Peptide Science