15960-05-1

Basic information

• Product Name: 2-AMINO-4,4,4-TRIFLUOROBUTYRIC ACID
• Synonyms: 3-trifluoromethylalanine;(2S)-4,4,4-Trifluoro-2-aminobutanoic acid;(S)-3-(Trifluoromethyl)-2-aminopropanoic acid;2-(2,2,2-Trifluoroethyl)-L-glycine;(S)-2-amino-4,4,4-trifluorobutanoic acid
• CAS NO: 15960-05-1
• Molecular Formula: C₄H₆F₃NO₂
• Molecular Weight: 157.09
• Mol File: 15960-05-1.mol

Chemical Properties

• Melting Point: 260-265°C
• Boiling Point: 185.2°Cat760mmHg
• Flash Point: 65.8°C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.3293 (estimate)
• Vapor Pressure: 0.321mmHg at 25°C
• Refractive Index: 1.391
• CAS DataBase Reference: 2-AMINO-4,4,4-TRIFLUOROBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4,4,4-TRIFLUOROBUTYRIC ACID(15960-05-1)
• EPA Substance Registry System: 2-AMINO-4,4,4-TRIFLUOROBUTYRIC ACID(15960-05-1)

Safety Data

• Hazardous Substances Data: 15960-05-1(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder

InChI:InChI=1/C4H6F3NO2/c5-4(6,7)1-2(8)3(9)10/h2H,1,8H2,(H,9,10)/t2-/m1/s1

Upstream product

• 120097-65-6 2-Acetylamino-4,4,4-trifluoro-butyric acid 
• 15960-04-0 N-(2-Trifluoracetylamino-4,4,4-trifluor-L-butyryl)-L-glutaminsaeure-dimethylester 

Downstream Products

• 1219145-37-5 (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4,4,4-trifluorobutanoic acid 

Relevant articles and documents

Expedient Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid via Alkylation of Chiral Nucleophilic Glycine Equivalent

Here we disclose a practical asymmetric synthesis of an enantiomerically 97.8% ee pure N-Fmoc derivative of (S)-2-amino-4,4,4-trifluorobutanoic acid performed on >10 g scale of the target product. The method is based on alkylation (CF3-CH2-I) of a new generation of a chiral nucleophilic equivalent conducted at ambient temperature with an excellent stereochemical outcome. The developed protocol does not require any chromatographic separations and includes only one purification step via recrystallization of the final product.

MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF

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

MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF

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

Helix propensity of highly fluorinated amino acids

Highly fluorinated amino acids have been used to stabilize helical proteins for potential application in various protein-based biotechnologies. To gain further insight into the effect of these highly fluorinated amino acids on helix formation exclusively, we measured the helix propensity of three highly fluorinated amino acids: (S)-5,5,5,5′,5′,5′-hexafluoroleucine (Hfl), (S)-2-amino-4,4,4-trifluorobutyric acid (Atb), and (S)-pentafluorophenylalanine (Pff). We have developed a short chemoenzymatic synthesis of Hfl with extremely high enantioselectivity (>99%). To measure the helix propensity (w) of the amino acids, alanine-based peptides were synthesized, purified, and investigated by circular dichroism spectroscopy (CD). On the basis of the CD data, the helix propensity of hydrocarbon amino acids can decrease up to 24-fold (1.72 kcal·mol-1·residue-1) upon fluorination. This difference in helix propensity has previously been overlooked in estimating the magnitude of the fluoro-stabilization effect (which has been estimated to be 0.32-0.83 kcal·mol-1·residue-1 for Hfl), resulting in a gross underestimation. Therefore, the full potential of the fluoro-stabilization effect should provide even more stable proteins than the fluoro-stabilized proteins to date. Copyright

Stereoselective Conversions of t-Butyl rac-, (R)-, or (S)-5-Alkylidene-2-t-butyl-3-methyl-4-oxo-1-imidazolidinecarboxylates (Chiral 2,3-Dehydroamino Acid Derivatives) and Preparation of Some Nonproteinogenic Amino Acids

The reactivity of the alkylidene derivatives 1-11 specified in the title and prepared in two operational steps from commercially available Boc-BMI and aldehydes is investigated. - According to high-field 1H-NMR analysis of the crude products, additions of H-H and D-D (catalytic hydrogenation, products 12-20), of R-H (BF3-activated R2CuLi/LiI and protonation, products 21-29), and of Cl2C (CHCl3/NaOH, products 33,34) occur with complete selectivity from the face opposite to the t-butyl group.The doubly unsaturated carbonyl derivative 11 reacts with dibutyl cuprate in the δ position, again with formation of a single diastereomer 32, while trifluoroethylidene-Boc-BMI 3a is reduced to the difluoro analogue 30 by this cuprate. - Li dienolates are generated by deprotonation with LDA of the ethylidene (2a) and butylidene compound 4a; subsequent alkylations (with primary and secondary halides, products 35-41) and hydroxyalkylations (with aldehydes, products 42-44) lead to single products of electrophilic attack in the α carbonyl position (C-5 of the imidazolidinone ring) under kinetic control.On the other hand, reaction of the 2a-derived dienolate with benzaldehyde under equilibrating conditions furnishes the four possible (E/R, E/S, Z/R, and Z/S) γ adducts 45-48. - A combination of methods - 1H- and 13C-NMR spectroscopy, NOE measurements, spectroscopic analogies, chemical correlation (with authentic samples or by spectroscopic or optical comparison), and X-ray analysis (Table 1, Figure 1, Schemes 1 and 2) - is used to assign the product configurations and thus the stereochemical course of the reactions.Some unusual amino acids (50-52, 54, 55) are prepared by hydrolysis of the corresponding imidazolidinones. Key words: Amino acids, dehydro-, chiral/ Amino acids, nonproteinogenic/ Michael additions of cuprates/ a5-Reactivi ty of doubly unsaturated carbonyl compounds/ Kinetic d2-versus thermodynamic d4-reactivity of Li dienolates