Abstract
Synthetic studies on fluorinated β-amino acids and β-peptides have expanded rapidly in recent years, and particularly significant are those methods giving access to the target compounds in enantiomerically pure form. Two main strategies have been investigated, namely selective fluorination of appropriate functional groups in β-amino acid frameworks, and exploitation of already fluorinated small molecules for their use as synthetic building blocks. In addition, fluorine-containing β-lactams have often been employed as synthetic intermediates for the preparation of the corresponding β-amino acids. A large variety of acyclic β-amino acids has been reported, containing one or two fluorine atoms at the α-position, as well as α- or β-fluoroalkyl substituents. In contrast, fluorinated cyclic derivatives are much more unusual. Furthermore, the first examples of peptidic molecules containing fluorinated β-amino acids in combination with non fluorinated α- or β-amino acids have recently appeared. These compounds have been studied in terms of structure, proteolytic stability and biological activity.
Current Organic Chemistry
Title: Recent Developments in the Synthesis of Fluorinated β-Amino Acids
Volume: 14 Issue: 9
Author(s): Jose Luis Acena, Antonio Simon-Fuentes and Santos Fustero
Affiliation:
Abstract: Synthetic studies on fluorinated β-amino acids and β-peptides have expanded rapidly in recent years, and particularly significant are those methods giving access to the target compounds in enantiomerically pure form. Two main strategies have been investigated, namely selective fluorination of appropriate functional groups in β-amino acid frameworks, and exploitation of already fluorinated small molecules for their use as synthetic building blocks. In addition, fluorine-containing β-lactams have often been employed as synthetic intermediates for the preparation of the corresponding β-amino acids. A large variety of acyclic β-amino acids has been reported, containing one or two fluorine atoms at the α-position, as well as α- or β-fluoroalkyl substituents. In contrast, fluorinated cyclic derivatives are much more unusual. Furthermore, the first examples of peptidic molecules containing fluorinated β-amino acids in combination with non fluorinated α- or β-amino acids have recently appeared. These compounds have been studied in terms of structure, proteolytic stability and biological activity.
Export Options
About this article
Cite this article as:
Luis Acena Jose, Simon-Fuentes Antonio and Fustero Santos, Recent Developments in the Synthesis of Fluorinated β-Amino Acids, Current Organic Chemistry 2010; 14 (9) . https://dx.doi.org/10.2174/138527210791111777
DOI https://dx.doi.org/10.2174/138527210791111777 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...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
- Announcements