16198-60-0

Basic information

• Product Name: HEXAFLUOROLEUCINE
• Synonyms: HEXAFLUOROLEUCINE;2-AMINO-5,5,5-TRIFLUORO-4-TRIFLUOROMETHYL-PENTANOIC ACID;Hexafluoroleucine 97%;Hexafluoroleucine97%;2-Amino-5,5,5-trifluoro-4-trifluoromethyl-pentanoic acid HCl;Hexafluoro-DL-leucine;2-Amino-5,5,5-trifluoro-4-trifluoromethyl pentanoic acid hydrochloride
• CAS NO: 16198-60-0
• Molecular Formula: C6H7F6NO2
• Molecular Weight: 239.12
• Product Categories: pharmacetical
• Mol File: 16198-60-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: >220°C
• Boiling Point: 224.672°C at 760 mmHg
• Flash Point: 89.679°C
• Appearance: /
• Density: 1.473g/cm³
• Vapor Pressure: 0.033mmHg at 25°C
• Refractive Index: 1.362
• CAS DataBase Reference: HEXAFLUOROLEUCINE(CAS DataBase Reference)
• NIST Chemistry Reference: HEXAFLUOROLEUCINE(16198-60-0)
• EPA Substance Registry System: HEXAFLUOROLEUCINE(16198-60-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 16198-60-0(Hazardous Substances Data)

Usage

General Description

Hexafluoroleucine is a synthetic, halogenated amino acid analog that is used in scientific research. It is an analog of leucine, an essential amino acid needed for the synthesis of proteins in human body, but it is made artificially with the addition of six fluorine atoms instead. This chemical is primarily used in biochemical research, especially in structural studies of proteins, to investigate the effects of fluorination on protein structure and function. Its properties can enable more precise structural determination of proteins or force proteins to change conformation, offering insights into protein folding, dynamics, and stability. The chemical is not naturally occurring and can be toxic, so its use is primarily limited to laboratory settings.

InChI:InChI=1/C6H7F6NO2/c1-4(2,7)6(9,10)5(8,3(14)15)13(11)12/h1-2H3,(H,14,15)

Upstream product

• 16063-98-2 2-amino-5,5,5-trifluoro-4-(trifluoromethyl)pentanoic acid 
• 478548-21-9 tert-butyl (2S)-2-[[(benzyloxy)carbonyl]amino]-5,5,5-trifluoro-4-(trifluoromethyl)pentanoate 
• 1053719-24-6 oxalic acid 3-benzyloxycarbonylamino-3-tert-butoxycarbonyl-1,1-bis-trifluoromethyl-propyl ester phenyl ester 
• 478548-20-8 tert-butyl (2S)-2-[[(benzyloxy)carbonyl]amino]-5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pentanoate 
• 201930-83-8 5,5,5-trifluoro-2-oxo-4-trifluoromethyl-pentanoic acid ethyl ester 

Downstream Products

• 149560-64-5 (S)-5,5,5,5',5',5'-hexafluoroleucine 
• 918667-71-7 (S)-2-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-5,5,5-trifluoro-4-(trifluoromethyl)-pentanoic acid 

Relevant articles and documents

MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Chemoenzymatic synthesis of (S)-hexafluoroleucine and (S)- tetrafluoroleucine

We have developed a short chemoenzymatic synthesis for both (S)-5,5,5,5′,5′,5′-hexafluoroleucine (Hfl) and (S)-5,5,5′,5′-tetrafluoroleucine (Qfl) on gram scale. Qfl was incorporated into a peptide using standard solid-phase peptide synthesis protocols to measure its helix propensity. The helix propensity for Qfl is 0.68 kcal·mol-1 more favorable compared to Hfl.

Process for preparing single enantiomers of 5,5,5,5',5',5'-hexafluoroleucine and protected analogs

A process for synthesizing L and D-5,5,5,5′,5′,5′-hexafluoroleucine and protected analogs is disclosed. These compounds have utility in the preparation of fluorous peptides and proteins, which display interesting and unusual properties including strong self-association and an affinity for lipid bilayers.