Abstract
Bicyclic peptides have received interest as anticancer agents, protease inhibitors, antibiotics, receptor antagonists, artificial receptors and models of various structural motives of proteins. Their common characteristic feature, limited conformational freedom of the backbone, plays a central role in all these applications. The same feature poses a challenge for synthetic organic chemists. Additional levels have to be included in the protecting group strategy to ensure the desired regioselectivity of cyclization and still the yields tend to be low, owing to increasing rigidity that cyclizations, in particular the second one, result in. The present review is aimed at summarizing the strategies described for the synthesis of various types of bicyclic peptides, originally in solution-phase and nowadays more often on a solid-support.
Keywords: Solid-phase synthesis., bicyclic peptides, protecting groups, cyclization, peptide coupling
Current Organic Synthesis
Title: Synthesis of Bicyclic Peptides
Volume: 3 Issue: 3
Author(s): Tuomas Karskela, Pasi Virta and Harri Lonnberg
Affiliation:
Keywords: Solid-phase synthesis., bicyclic peptides, protecting groups, cyclization, peptide coupling
Abstract: Bicyclic peptides have received interest as anticancer agents, protease inhibitors, antibiotics, receptor antagonists, artificial receptors and models of various structural motives of proteins. Their common characteristic feature, limited conformational freedom of the backbone, plays a central role in all these applications. The same feature poses a challenge for synthetic organic chemists. Additional levels have to be included in the protecting group strategy to ensure the desired regioselectivity of cyclization and still the yields tend to be low, owing to increasing rigidity that cyclizations, in particular the second one, result in. The present review is aimed at summarizing the strategies described for the synthesis of various types of bicyclic peptides, originally in solution-phase and nowadays more often on a solid-support.
Export Options
About this article
Cite this article as:
Karskela Tuomas, Virta Pasi and Lonnberg Harri, Synthesis of Bicyclic Peptides, Current Organic Synthesis 2006; 3 (3) . https://dx.doi.org/10.2174/157017906777934917
DOI https://dx.doi.org/10.2174/157017906777934917 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
Call for Papers in Thematic Issues
Biorthogonal Chemistry: A translational chemical tool for in vivo applications
After the discovery in 1990, bioorthogonal chemistry encompassed a set of diverse fast-paced selective chemical reactions, facilitating the study of biomolecules under physiological aura without intervening in the biochemical processes. Over the past two decades, significant progress has been witnessed in bioorthogonal reactions such as Staudinger ligation, metal-catalyzed coupling reactions, ...read more
Design and Synthesis of Green Pesticides
The development of green new pesticides is currently one of the hotspots in the field of pesticide research, aiming to develop efficient, environmentally friendly, and safe pesticide products to meet the needs of modern agricultural production. Green new pesticides prioritize environmental friendliness and ecological safety. Therefore, during the research and ...read more
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Organic Radical Chemistry
Organic radical chemistry has a history of more than 110 years. In the past decade, we have witnessed new directions for organic radical chemistry. It has now become an exciting area of research in organic chemistry, and new discoveries can be seen every day in various aspects of radical chemistry ...read more
Related Journals
- 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