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Phase Diagrams02:39

Phase Diagrams

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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...
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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.
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Structures of Solids

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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...
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Phase Transitions02:31

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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...
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Network Covalent Solids

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Total Solid-Phase Synthesis of Dehydroxy Fengycin Derivatives.

Cristina Rosés1, Cristina Camó1, Àngel Oliveras1

  • 1LIPPSO, Department of Chemistry , University of Girona , Maria Aurèlia Capmany 69 , 17003 Girona , Spain.

The Journal of Organic Chemistry
|December 12, 2018
PubMed
Summary

Researchers developed a novel solid-phase synthesis for dehydroxy fengycin derivatives. This method enhances macrolactone stability, particularly with specific tyrosine configurations, marking a significant advancement in cyclic lipodepsipeptide synthesis.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Peptide Synthesis

Background:

  • Dehydroxy fengycins are a class of cyclic lipodepsipeptides with potential biological activities.
  • Efficient synthesis of complex peptide structures like fengycin derivatives is challenging.
  • Solid-phase synthesis offers advantages for constructing peptide-based molecules.

Purpose of the Study:

  • To develop a rapid and efficient solid-phase strategy for synthesizing dehydroxy fengycin derivatives.
  • To investigate the influence of amino acid composition and N-terminal acylation on macrolactone stability.
  • To explore the impact of stereochemistry on the stability of cyclic lipodepsipeptides.

Main Methods:

  • Solid-phase synthesis involving Tyr linkage to Wang resin via Mitsunobu reaction.
  • Peptide sequence elongation, N-terminal acylation, and phenol esterification with Ile.
  • Final macrolactamization to form the cyclic structure.

Main Results:

  • A novel solid-phase strategy for dehydroxy fengycin derivative synthesis was established.
  • Macrolactone stability was significantly influenced by amino acid composition and N-terminal acyl group.
  • Cyclic lipodepsipeptides with l-Tyr³/d-Tyr⁹ configuration exhibited greater stability than those with opposite configurations.

Conclusions:

  • This study presents the first total solid-phase synthesis approach for dehydroxy fengycin derivatives.
  • The developed method provides a stable platform for generating fengycin analogs.
  • Stereochemical configuration of tyrosine residues is a critical factor for macrolactone stability.