87720-55-6

Basic information

• Product Name: Fmoc-4,5-dehydro-L-leucine
• Synonyms: FMOC-ALPHA,BETA-DEHYDRO-LEUCINE;FMOC-4,5-DEHYDRO-LEUCINE;FMOC-4,5-DEHYDRO-LEU-OH;FMOC-4,5-DEHYDRO-L-LEUCINE;FMOC-4,5-DEHYRO-LEU-OH;FMOC-2,3-DEHYDROLEU-OH;FMOC-DELTA-LEU-OH;FMOC-DLE(4,5)-OH
• CAS NO: 87720-55-6
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.4
• Mol File: 87720-55-6.mol

Chemical Properties

• Boiling Point: 569.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.223±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 3.74±0.10(Predicted)
• CAS DataBase Reference: Fmoc-4,5-dehydro-L-leucine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-4,5-dehydro-L-leucine(87720-55-6)
• EPA Substance Registry System: Fmoc-4,5-dehydro-L-leucine(87720-55-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 87720-55-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Fmoc-4,5-dehydro-L-leucine is used as a reagent in the solid-phase preparation of ε-lysylcarbonylphenoxyacetic acids. This application is significant for studying the selective inhibition of human aldose reductase over aldehyde reductase, which are key enzymes involved in various metabolic pathways and have been implicated in the development of diabetic complications and other diseases.
In the field of pharmaceutical research, the selective inhibition of aldose reductase has been a topic of interest due to its potential therapeutic benefits in managing diabetic complications, such as cataract formation, neuropathy, and retinopathy. By using Fmoc-4,5-dehydro-L-leucine in the synthesis of ε-lysylcarbonylphenoxyacetic acids, researchers can develop novel inhibitors with improved selectivity and potency, leading to more effective treatments for these conditions.
Furthermore, the unique structural features of Fmoc-4,5-dehydro-L-leucine may also contribute to the development of other bioactive peptides and peptidomimetics with potential applications in various therapeutic areas. The ability to incorporate this unusual amino acid into peptide sequences allows for the exploration of new chemical space and the discovery of innovative drug candidates with unique mechanisms of action.

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Relevant articles and documents

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.

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.

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