409333-54-6

Basic information

• Product Name: BOC-D,L-4,4,4-TRIFLUOROVALINE
• Synonyms: Valine, N-[(1,1-dimethylethoxy)carbonyl]-4,4,4-trifluoro-;2-(Boc-amino)-4,4,4-trifluoro-3-methylbutyric acid;2-(tert-butoxycarbonylamino)-4,4,4-trifluoro-3-methylbutanoic acid
• CAS NO: 409333-54-6
• Molecular Formula: C10H16F3NO4
• Molecular Weight: 271.24
• Mol File: 409333-54-6.mol

Chemical Properties

• Boiling Point: 331.5°C at 760 mmHg
• Flash Point: 154.3°C
• Appearance: /
• Density: 1.245g/cm³
• Vapor Pressure: 3.01E-05mmHg at 25°C
• Refractive Index: 1.424
• CAS DataBase Reference: BOC-D,L-4,4,4-TRIFLUOROVALINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D,L-4,4,4-TRIFLUOROVALINE(409333-54-6)
• EPA Substance Registry System: BOC-D,L-4,4,4-TRIFLUOROVALINE(409333-54-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 409333-54-6(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry and Pharmaceutical Research:
BOC-D,L-4,4,4-TRIFLUOROVALINE is used as a building block for the synthesis of novel peptide-based drugs and pharmaceuticals. Its unique properties contribute to the enhancement of biological activity and stability of the resulting peptide molecules.
Used in Drug Discovery and Development:
BOC-D,L-4,4,4-TRIFLUOROVALINE is used as a valuable tool in drug discovery and development. Its incorporation into peptide molecules has potential applications in the development of therapeutics for various diseases and medical conditions, making it an important asset in advancing pharmaceutical research.

InChI:InChI=1/C10H16F3NO4/c1-5(10(11,12)13)6(7(15)16)14-8(17)18-9(2,3)4/h5-6H,1-4H3,(H,14,17)(H,15,16)

Upstream product

• 952714-68-0 (S)-4-benzyl-3-((S)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one 
• 952714-69-1 (S)-3-((2S,3S)-2-azido-4,4,4-trifluoro-3-methylbutanoyl)-4-benzyloxazolidin-2-one 
• 1414349-18-0 tert-butyl ((2R,3S)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4,4,4-trifluoro-3-methyl-1-oxobutan-2-yl)carbamate 
• 1414348-97-2 (S)-4-benzyl-3-((2S,3R)-2-bromo-4,4,4-trifluoro-3-methylbutanoyl)-oxazolidin-2-one 
• 1414348-99-4 (S)-3-((2R,3S)-2-azido-4,4,4-trifluoro-3-methylbutanoyl)-4-benzyloxazolidin-2-one 
• 1414348-90-5 (S)-4-benzyl-3-((R)-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1414349-15-7 (S)-3-((2S,3R)-2-azido-4,4,4-trifluoro-3-methylbutanoyl)-4-benzyloxazolidin-2-one 
• 1414349-17-9 tert-butyl ((2R,3R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4,4,4-trifluoro-3-methyl-1-oxobutan-2-yl)carbamate 
• 1414349-00-0 (S)-3-((2R,3R)-2-azido-4,4,4-trifluoro-3-methylbutanoyl)-4-benzyloxazolidin-2-one 
• 1414348-93-8 tert-butyl ((2S,3R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4,4,4-trifluoro-3-methyl-1-oxobutan-2-yl)carbamate 
• 1414348-98-3 (S)-4-benzyl-3-((2S,3S)-2-bromo-4,4,4-trifluoro-3-methylbutanoyl)oxazolidin-2-one 
• 888725-61-9 tert-butyl (1R,2S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3,3-trifluoro-2-methylpropyl carbamate 
• 888725-62-0 tert-butyl (2S,3R,4S)-1,1,1-trifluoro-4,5-dihydroxy-2-methylpentan-3-ylcarbamate 

Relevant articles and documents

A coiled coil with a fluorous core

The design, synthesis, and structural characterization of a highly fluorinated peptide system based on the coiled coil region of the yeast transcription factor GCN4 is described. All four leucine residues (a position) and three valine residues (d position) were replaced by the unnatural amino acids 5,5,5-trifluoroleucine and 4,4,4-trifluorovaline, respectively. The peptide is highly α-helical at low micromolar concentrations as judged by circular dichroism spectra, sediments as a dimeric species in the 5-30 μM concentration range, and exhibits a dimer melting temperature that is 15 °C higher than a control peptide with a hydrocarbon core. Furthermore, the apparent free energy of unfolding as calculated from guanidinium hydrochloride denaturation experiments is larger by ～1.0 kcal/mol for the fluorinated peptide than its hydrocarbon counterpart. We conclude that additional stability is derived from sequestering the more hydrophobic trifluoromethyl groups from aqueous solvent. These studies introduce a new paradigm in the design of molecular self-assembling systems, one based on orthogonal solubility properties of liquid phases.

Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: Synthesis of chiral fluorinated amino acids

A novel conjugate hydrofluoroalkylation of α,β-unsaturated acyl-oxazolidinones is described. Using this method, enantiomerically pure β-trifluoromethylated amino acids were prepared. Trifluorovaline and trifluoroisoleucine were incorporated into peptides and found to show extremely low α-helix propensities.

Indium-mediated diastereoselective allylation of D- and L-glyceraldimines with 4-bromo-1,1,1-trifluoro-2-butene: Highly stereoselective synthesis of 4,4,4-trifluoroisoleucines and 4,4,4-trifluorovaline

A practical and efficient route for the stereoselective synthesis of (2R,3S)- and (2S,3R)-4,4,4-trifluoroisoleucines and (2R,3S)-4,4,4- trifluorovaline was developed. Indium-mediated allylation of (R)-N-benzyl-2,3-O-isopropylideneglyceraldimine 7 with 4-bromo-1,1,1-trifluoro- 2-butene 4 gave the desired homoallylic amine 8 in high diastereoselectivity (>95% de) with moderate yield. The Cbz-protected (2R,35)-4,4,4- trifluoroisoleucine 14 and Boc-protected (2R,3S)-4,4,4-trifluorovaline 21 were then readily prepared from 8. In addition, following the same procedure, Cbz-protected (2S,3R)-4,4,4-trifluoroisoleucine 28, the enantiomer of 14, was prepared starting from (S)-N-benzyl-2,3-O-isopropylideneglyceraldimine 24.

Non-racemic hexafluoreleucine, and methods of making and using it

One aspect of the invention relates to hexafluoroleucine and congeners thereof, and methods of making the compounds. Another aspect of the nvention relates to the synthesis of protein cores comprising hexafluoroleucine and congeners thereof. Certain peptides comprising hexafluorleucine and congeners thereof have been characterized using comparative biophysical studies. In general, the fluorinated peptides show higher thermal stability and enhanced resistance to chemical denaturation. Further, mixed hydrocarbonfluorocarbon cores self-sort into homogeneous bundles, suggesting new avenues for the design and manipulation of protein-protein interfaces.