247127-51-1

Basic information

• Product Name: N-α –Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohe
• Synonyms: Fmoc-(N-beta-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl)-L-alpha,beta-diaminopropionic aci;(S)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-((1-(4,4-diMethyl-2,6-dioxocyclohexylidene)ethyl)aMino)propanoic acid;3-[[1-(4,4-Dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine;Fmoc-(N-beta-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl)-L-alpha,beta-diaminopropionic;(9H-Fluoren-9-yl)MethOxy]Carbonyl Dap(Dde)-OH
• CAS NO: 247127-51-1
• Molecular Formula: C₂₈H₃₀N₂O₆
• Molecular Weight: 490.5476
• Product Categories: amino acids;Unusual Amino Acids
• Mol File: 247127-51-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 719.2±60.0 °C(Predicted)
• Appearance: /
• Density: 1.270±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.47±0.10(Predicted)
• CAS DataBase Reference: N-α –Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohe(CAS DataBase Reference)
• NIST Chemistry Reference: N-α –Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohe(247127-51-1)
• EPA Substance Registry System: N-α –Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohe(247127-51-1)

Safety Data

• Hazardous Substances Data: 247127-51-1(Hazardous Substances Data)

Usage

General Description

The chemical N-α –Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohe is a modified amino acid derivative commonly used in peptide synthesis. It is composed of N-α-Fmoc, which is a protective group for the amine of the amino acid, and N-β-1-(4,4-dimethyl-2,6-dioxocyclohe, which is a substituted beta-amino acid. This chemical is often used in solid-phase peptide synthesis to selectively modify and add specific functional groups to peptides, allowing for the creation of a wide variety of peptide sequences with specific properties and functions. The presence of the Fmoc group allows for the selective deprotection and coupling of the amino acid during the synthesis process, making it an important tool for bioorganic chemistry research and the pharmaceutical industry.

Upstream product

• 126-81-8 dimedone 
• 1755-15-3 2-acetyldimedone 
• 181954-34-7 3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 

Relevant articles and documents

On-Resin Preparation of Allenamidyl Peptides: A Versatile Chemoselective Conjugation and Intramolecular Cyclisation Tool

The ability to modify peptides and proteins chemoselectively is of continued interest in medicinal chemistry, with peptide conjugation, lipidation, stapling, and disulfide engineering at the forefront of modern peptide chemistry. Herein we report a robust method for the on-resin preparation of allenamide-modified peptides, an unexplored functionality for peptides that provides a versatile chemical tool for chemoselective inter- or intramolecular bridging reactions with thiols. The bridging reaction is biocompatible, occurring spontaneously at pH 7.4 in catalyst-free aqueous media. By this “click” approach, a model peptide was successfully modified with a diverse range of alkyl and aryl thiols. Furthermore, this technique was demonstrated as a valuable tool to induce spontaneous intramolecular cyclisation by preparation of an oxytocin analogue, in which the native disulfide bridge was replaced with a vinyl sulfide moiety formed by thia-Michael addition of a cysteine thiol to the allenamide handle.