Abstract
Cyclosporin O (CyO), an immunosuppressent cyclic undecapeptide, was synthesized by convergent approach employing Bsmoc-Nmethyl amino acid fluorides and Potassium Salt of 7-Aza-1-hydroxybenzotriazole (KOAt) in solution by stepwise assembly. The couplings were found to be epimerisation free. The difficulty in the coupling of four consecutive N-methyl amino acids at position 8, 9, 10 and 11 was overcome by repeating the coupling thrice at these critical positions. All the ten protected peptide fragments of CyO starting from the dipeptide to the undecapeptide and final protected as well as CyO were isolated and fully characterized.
Keywords: Cyclosporin O, Acid fluoride, KOAt, N-Methyl amino acid, Diethyl amine
Protein & Peptide Letters
Title: Total Synthesis of Cyclosporin O: Exploring the Utility of Bsmoc-NMe- Amino Acid Fluorides and KOAt
Volume: 16 Issue: 3
Author(s): Vommina Venkata Sureshbabu, Subramanyam J. Tantry, Gundala Chennakrishnareddy and Govindappa Nagendra
Affiliation:
Keywords: Cyclosporin O, Acid fluoride, KOAt, N-Methyl amino acid, Diethyl amine
Abstract: Cyclosporin O (CyO), an immunosuppressent cyclic undecapeptide, was synthesized by convergent approach employing Bsmoc-Nmethyl amino acid fluorides and Potassium Salt of 7-Aza-1-hydroxybenzotriazole (KOAt) in solution by stepwise assembly. The couplings were found to be epimerisation free. The difficulty in the coupling of four consecutive N-methyl amino acids at position 8, 9, 10 and 11 was overcome by repeating the coupling thrice at these critical positions. All the ten protected peptide fragments of CyO starting from the dipeptide to the undecapeptide and final protected as well as CyO were isolated and fully characterized.
Export Options
About this article
Cite this article as:
Sureshbabu Venkata Vommina, Tantry J. Subramanyam, Chennakrishnareddy Gundala and Nagendra Govindappa, Total Synthesis of Cyclosporin O: Exploring the Utility of Bsmoc-NMe- Amino Acid Fluorides and KOAt, Protein & Peptide Letters 2009; 16 (3) . https://dx.doi.org/10.2174/092986609787601813
DOI https://dx.doi.org/10.2174/092986609787601813 |
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
-
Design, Synthesis, SAR Study, Antimicrobial and Anticancer Evaluation of Novel 2-Mercaptobenzimidazole Azomethine Derivatives
Mini-Reviews in Medicinal Chemistry Antimicrobial Activities of 1-H-Benzimidazole-based Molecules
Current Topics in Medicinal Chemistry Allosterism at Muscarinic Receptors: Ligands and Mechanisms
Mini-Reviews in Medicinal Chemistry Comparison the Effect of Arbidol Plus Hydroxychloroquine vs Hydroxychloroquine Alone in Treatment of COVID-19 Disease: A Randomized Clinical Trial
Current Respiratory Medicine Reviews Application of Nano- and Micro-Particles on the Topical Therapy of Skin-Related Immune Disorders
Current Pharmaceutical Design The Changing Face of Hepatitis C: Recent Advances on HCV Inhibitors Targeting NS5A
Current Medicinal Chemistry Potentials of Diphenyl Ether Scaffold as a Therapeutic Agent: A Review
Mini-Reviews in Medicinal Chemistry Triazole Use in the Nursery: Fluconazole, Voriconazole, Posaconazole, and Ravuconazole
Current Drug Metabolism Efficient Green Synthesis of Bis(3-indolyl)phenylmethanes Catalyzed by 1- (Benzenesulfonyl)-3-methyl-1H-imidazolium Chlorides
Letters in Organic Chemistry Snake Venom Peptides and Low Mass Proteins: Molecular Tools and Therapeutic Agents
Current Medicinal Chemistry Advances and Progress in Chagas Disease Drug Discovery
Current Topics in Medicinal Chemistry α<sub>2</sub> Adrenoceptor: a Target for Neuropathic Pain Treatment
Mini-Reviews in Medicinal Chemistry Diabetes and the Impairment of Reproductive Function: Possible Role of Mitochondria and Reactive Oxygen Species
Current Diabetes Reviews Synthesis and Antifungal Activity of 1,2,4-triazole Derivatives Containing Cyclopropane Moiety
Letters in Drug Design & Discovery Peptide Mediated siRNA Delivery
Current Topics in Medicinal Chemistry COVID-19-associated Coagulopathy: Role of Vitamins D and K
Current Pharmaceutical Biotechnology Genetic-TLBO Algorithm for Power System Stabilizer
Current Signal Transduction Therapy The Antidiabetic PPARγ Ligands: An Update on Compounds in Development
Current Medicinal Chemistry - Immunology, Endocrine & Metabolic Agents Structure-Based Development of Antagonists for Chemokine Receptor CXCR4
Current Computer-Aided Drug Design Nanotechnology-based Approaches for COVID-19: A Path Forward
Current Nanomaterials