Abstract
A convenient solid phase synthesis of a Thrombin Receptor Glycopeptide Mimetic analogue namely, 1-OMethyl- 2-N-{1’-(argininocarbonyl)-4’-[(4’’-fluoro)-benzylamido]-cyclohexane}-glucosamine using Fmoc/tBu methodology and the 4-Methoxybenzhydryl bromide resin is described. The synthesized analogue was purified by Reverse Phase High Performance Liquid Chromatography (RP-HPLC) and was identified by Electron Spray Ionization-Mass Spectrometry (ESI-MS) and Nuclear Magnetic Resonance (NMR). The synthetic protocol introduced for the first time successfully the acid sensitive 4-Methoxybenzhydryl bromide resin as a scaffold for the synthesis of glycopeptides resulting in high yield reactions. This synthetic procedure could be a general one for the convenient synthesis of such glyco compounds as the method was used for the first time to glycosylate a non peptide mimetic of an important protein sequence, in particular of the thrombin receptor active site S42FLLR46.
Keywords: Glycopeptides, glycoproteins, 4-Methoxybenzhydryl bromide resin (MDMR-Br), Fmoc/tBu solid phase synthesis, glucosamine
Protein & Peptide Letters
Title: Solid Phase Synthesis of a Glycopeptide Analogue Using the Acid Sensitive 4-Methoxybenzhydryl Bromide Resin
Volume: 15 Issue: 1
Author(s): Theodore Tselios, Konstantinos Kelaidonis, Amalia Resvani, Konstantinos Prousalis, John Matsoukas and Theodore Tsegenidis
Affiliation:
Keywords: Glycopeptides, glycoproteins, 4-Methoxybenzhydryl bromide resin (MDMR-Br), Fmoc/tBu solid phase synthesis, glucosamine
Abstract: A convenient solid phase synthesis of a Thrombin Receptor Glycopeptide Mimetic analogue namely, 1-OMethyl- 2-N-{1’-(argininocarbonyl)-4’-[(4’’-fluoro)-benzylamido]-cyclohexane}-glucosamine using Fmoc/tBu methodology and the 4-Methoxybenzhydryl bromide resin is described. The synthesized analogue was purified by Reverse Phase High Performance Liquid Chromatography (RP-HPLC) and was identified by Electron Spray Ionization-Mass Spectrometry (ESI-MS) and Nuclear Magnetic Resonance (NMR). The synthetic protocol introduced for the first time successfully the acid sensitive 4-Methoxybenzhydryl bromide resin as a scaffold for the synthesis of glycopeptides resulting in high yield reactions. This synthetic procedure could be a general one for the convenient synthesis of such glyco compounds as the method was used for the first time to glycosylate a non peptide mimetic of an important protein sequence, in particular of the thrombin receptor active site S42FLLR46.
Export Options
About this article
Cite this article as:
Tselios Theodore, Kelaidonis Konstantinos, Resvani Amalia, Prousalis Konstantinos, Matsoukas John and Tsegenidis Theodore, Solid Phase Synthesis of a Glycopeptide Analogue Using the Acid Sensitive 4-Methoxybenzhydryl Bromide Resin, Protein & Peptide Letters 2008; 15 (1) . https://dx.doi.org/10.2174/092986608783330323
DOI https://dx.doi.org/10.2174/092986608783330323 |
Print ISSN 0929-8665 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5305 |
- 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
Related Articles
-
Chronic Inflammatory Diseases: Progress and Prospect with Herbal Medicine
Current Pharmaceutical Design Therapeutic Targeting of Chemokines and Chemokine Receptors in Multiple Sclerosis: Opportunities and Challenges
CNS & Neurological Disorders - Drug Targets Nitric Oxide and Inflammation
Current Medicinal Chemistry - Anti-Inflammatory & Anti-Allergy Agents Nano-formulations for Diagnostics and Therapeutics of Foot-and-Mouth Disease in Animals
Nanoscience & Nanotechnology-Asia The Importance of NAD in Multiple Sclerosis
Current Pharmaceutical Design The Effect of Psychological Stress and Social Isolation on Neuroimmunoendocrine Communication
Current Pharmaceutical Design The Potential Role of Pro-Inflammatory and Anti-Inflammatory Cytokines in Epilepsy Pathogenesis
Endocrine, Metabolic & Immune Disorders - Drug Targets Autoimmune Diseases and Atherosclerosis: The Inflammatory Connection
Current Immunology Reviews (Discontinued) Oxidative Stress Protection by Novel Telomerase Activators in Mesenchymal Stem Cells Derived from Healthy and Diseased Individuals
Current Molecular Medicine Antidepressants and Neuroinflammation: Can Antidepressants Calm Glial Rage Down?
Mini-Reviews in Medicinal Chemistry Therapeutic Targeting of Leukocyte Trafficking Across the Blood-Brain Barrier
Inflammation & Allergy - Drug Targets (Discontinued) The role of interleukin 35 in atherosclerosis
Current Pharmaceutical Design Clonal Expansion of Mitochondrial DNA Deletions and the Progression of Multiple Sclerosis
CNS & Neurological Disorders - Drug Targets Interleukin-21 in Immune and Allergic Diseases
Inflammation & Allergy - Drug Targets (Discontinued) Opioids and Opioid Maintenance Therapies: Their Impact on Monocyte-Mediated HIV Neuropathogenesis
Current HIV Research The Role of Neutrophils and TH17 Cells in the Immunopathology of Severe Asthmax
Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry Targeting the Prokineticin System to Control Chronic Pain and Inflammation
Current Medicinal Chemistry Role of Free Radicals and Poly(ADP-Ribose)Polymerase-1 in the Development of Spinal Cord Injury: New Potential Therapeutic Targets
Current Medicinal Chemistry P2X7 Receptors: Channels, Pores and More
CNS & Neurological Disorders - Drug Targets Virulence Mechanisms Displayed by Salmonella to Impair Dendritic Cell Function
Current Medicinal Chemistry