917099-00-4

Basic information

• Product Name: Fmoc-4,5-dehydro-D-leu-OH
• Synonyms: FMoc-(R)-2-Methallylglycine
• CAS NO: 917099-00-4
• Molecular Formula: C21H21NO4
• Molecular Weight: 351.4
• Mol File: 917099-00-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Store at?0-5°C
• CAS DataBase Reference: Fmoc-4,5-dehydro-D-leu-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-4,5-dehydro-D-leu-OH(917099-00-4)
• EPA Substance Registry System: Fmoc-4,5-dehydro-D-leu-OH(917099-00-4)

Safety Data

• Hazardous Substances Data: 917099-00-4(Hazardous Substances Data)

Usage

General Description

Fmoc-4,5-dehydro-D-leu-OH is a chemical compound that belongs to the class of amino acids. It is a derivative of the amino acid leucine, with a specific modification at the 4th and 5th carbon positions that leads to the formation of a double bond. This modification makes Fmoc-4,5-dehydro-D-leu-OH a unique and potentially valuable building block for the synthesis of peptides and other complex organic molecules. It can be used in peptide chemistry and drug discovery research, where the incorporation of non-natural amino acids can lead to the development of novel therapeutics with enhanced properties. Overall, Fmoc-4,5-dehydro-D-leu-OH has the potential to expand the synthetic toolbox available to chemists and advance the development of new biologically active molecules.

Upstream product

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Relevant articles and documents

Total Synthesis of the Death Cap Toxin Phalloidin: Atropoisomer Selectivity Explained by Molecular-Dynamics Simulations

Phallotoxins and amatoxins are a group of prominent peptide toxins produced by the death cap mushroom Amanita phalloides. Phalloidin is a bicyclic cyclopeptide with an unusual tryptathionin thioether bridge. It is a potent stabilizer of filamentous actin and in a fluorescently labeled form widely used as a probe for actin binding. Herein, we report the enantioselective synthesis of the key amino acid (2S,4R)-4,5-dihydroxy-leucine as a basis for the first total synthesis of phalloidin, which was accomplished by two different synthesis strategies. Molecular-dynamics simulations provided insights into the conformational flexibility of peptide intermediates of different reaction strategies and showed that this flexibility is critical for the formation of atropoisomers. By simulating the intermediates, rather than the final product, molecular-dynamics simulations will become a decisive tool in orchestrating the sequence of ring formation reactions of complex cyclic peptides.

Direct incorporation of unprotected ketone groups into peptides during solid-phase synthesis: Application to the one-step modification of peptides with two different biophysical probes for FRET

An amino acid bearing an unprotected ketone group, (2S)-aminolevulinic acid, was incorporated into a synthetic peptide using standard Fmoc-based solid-phase methods. The ketone group remained unharmed during the synthesis and provided a uniquely reactive functional group for covalent modification of the peptide. The ketone and the sulfhydryl group of a cysteine residue elsewhere in the peptide were reacted simultaneously with two different biophysical probes, enabling the site-specific installation of a donor and acceptor pair for FRET in one step without the need for differential side chain protection.

Synthesis of 2>- and 6>-Locust Adipokinetic Hormone

The syntheses of 2>- and 6>-locust adipokinetic hormone (LAKH) by the coupling of N-terminal hexapeptides prepared by the solid-phase method with a common C-terminal tetrapeptide synthesised in solution