Solid-Phase Synthesis and Circular Dichroism Study of β-ABpeptoids.
Ganesh A Sable1, Kang Ju Lee2, Hyun-Suk Lim3
1Department of Chemistry and Division of Advanced Material Science, Pohang University of Science and Technology (POSTECH), Pohang 37673, Korea. sganesh105@postech.ac.kr.
Molecules (Basel, Switzerland)
|January 10, 2019
Summary
Researchers developed novel β-ABpeptoids, a new class of peptidomimetic foldamers with backbone chirality. These molecules adopt defined folded structures, showing promise for biomedical and material science applications.
Area of Science:
- Chemical Biology
- Polymer Chemistry
- Biomaterials Science
Background:
- Developing peptidomimetic foldamers with predictable structures is a significant challenge.
- Previous work demonstrated α-ABpeptoids adopt folding conformations due to α-position chiral methyl groups.
Purpose of the Study:
- To introduce and characterize a new class of foldamers: β-ABpeptoids.
- To investigate the folding capabilities of β-ABpeptoids with backbone chirality.
Main Methods:
- Solid-phase synthesis of β-ABpeptoid oligomers (2-mer to 8-mer).
- Circular dichroism (CD) spectroscopy.
- Nuclear Magnetic Resonance (NMR) studies.
Main Results:
- A facile solid-phase synthetic route was established for β-ABpeptoids.
- β-ABpeptoid oligomers were synthesized in excellent yields.
- CD and NMR studies confirmed the adoption of ordered folding conformations.
Conclusions:
- β-ABpeptoids represent a novel class of peptidomimetic foldamers.
- These foldamers possess backbone chirality and form defined structures.
- Potential applications in biomedical and material sciences are indicated.
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Related Concept Videos
02:39Phase Diagrams
50.1K
A phase diagram combines plots of pressure versus temperature for the liquid-gas, solid-liquid, and solid-gas phase-transition equilibria of a substance. These diagrams indicate the physical states that exist under specific conditions of pressure and temperature and also provide the pressure dependence of the phase-transition temperatures (melting points, sublimation points, boiling points). Regions or areas labeled solid, liquid, and gas represent single phases, while lines or curves represent...
50.1K
01:07Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
4.6K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
4.6K
01:14Alkylation of β-Diester Enolates: Malonic Ester Synthesis
4.2K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
4.2K
02:37Metallic Solids
20.6K
Metallic solids such as crystals of copper, aluminum, and iron are formed by metal atoms. The structure of metallic crystals is often described as a uniform distribution of atomic nuclei within a “sea” of delocalized electrons. The atoms within such a metallic solid are held together by a unique force known as metallic bonding that gives rise to many useful and varied bulk properties.
All metallic solids exhibit high thermal and electrical conductivity, metallic luster, and malleability....
All metallic solids exhibit high thermal and electrical conductivity, metallic luster, and malleability....
20.6K
02:22Structures of Solids
17.7K
Solids in which the atoms, ions, or molecules are arranged in a definite repeating pattern are known as crystalline solids. Metals and ionic compounds typically form ordered, crystalline solids. A crystalline solid has a precise melting temperature because each atom or molecule of the same type is held in place with the same forces or energy. Amorphous solids or non-crystalline solids (or, sometimes, glasses) which lack an ordered internal structure and are randomly arranged. Substances that...
17.7K
02:31Phase Transitions
23.1K
Whether solid, liquid, or gas, a substance's state depends on the order and arrangement of its particles (atoms, molecules, or ions). Particles in the solid pack closely together, generally in a pattern. The particles vibrate about their fixed positions but do not move or squeeze past their neighbors. In liquids, although the particles are closely spaced, they are randomly arranged. The position of the particles are not fixed—that is, they are free to move past their neighbors to...
23.1K