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91917

Sigma-Aldrich

5,5,5-Trifluoro-DL-leucine

≥98.0% (sum of isomers, HPLC)

Synonym(s):

(±)-2-Amino-4-(trifluoromethyl)pentanoic acid

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About This Item

Empirical Formula (Hill Notation):
C6H10F3NO2
CAS Number:
2792-72-5
Molecular Weight:
185.14
MDL number:
MFCD00039528
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
329770097
NACRES:
NA.22

Assay

≥98.0% (sum of isomers, HPLC)

form

crystals

reaction suitability

reaction type: solution phase peptide synthesis

application(s)

peptide synthesis

SMILES string

CC(CC(N)C(O)=O)C(F)(F)F

InChI

1S/C6H10F3NO2/c1-3(6(7,8)9)2-4(10)5(11)12/h3-4H,2,10H2,1H3,(H,11,12)

InChI key

XFGVJLGVINCWDP-UHFFFAOYSA-N

Related Categories

General description

5,5,5-Trifluoro-DL-leucine, also known as trifluoroleucine, is an analog of L-leucine amino acid, often used to synthesize highly fluorinated peptides.

Application

5,5,5-trifluoroleucine can be incorporated into the coiled-coil peptides to increase their thermal stability.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Takahiro Oba et al.
Bioscience, biotechnology, and biochemistry, 69(7), 1270-1273 (2005-07-26)
We identified a new mutation, Asp578Tyr, in alpha-isopropylmalate synthase (a LEU4 gene product) that releases leucine feedback inhibition and causes hyperproduction of isoamyl alcohol (i-AmOH) in sake yeast. Spontaneous sake yeast mutants that express resistance to 5,5,5-trifluoro-DL-leucine (TFL) were isolated
Y Tang et al.
Biochemistry, 40(9), 2790-2796 (2001-03-22)
Substitution of leucine residues by 5,5,5-trifluoroleucine at the d-positions of the leucine zipper peptide GCN4-p1d increases the thermal stability of the coiled-coil structure. The midpoint thermal unfolding temperature of the fluorinated peptide is elevated by 13 degrees C at 30
Tatsuya Tominaga et al.
Biotechnology letters, 25(20), 1735-1738 (2003-11-25)
Saccharomyces servazzii plays a crucial role in the making of Japanese radish pickles. To make more flavorsome pickles, we sought to generate trifluoroleucine-resistant mutants of S. servazzii. The three resulting mutants could be classified into two types: one that produces
D I Johnson et al.
Journal of bacteriology, 155(1), 49-55 (1983-07-01)
Mutants of Escherichia coli K-12 resistant to either the threonine analog DL-alpha-amino-beta-hydroxyvaleric acid or the leucine analog 5',5',5'-trifluoro-DL-leucine were isolated. One DL-alpha-amino-beta-hydroxyvaleric acid-resistant mutant strain, designated SP572, constitutively expressed the thr and ilv operons. The mutant allele, avr-16, was localized
I Bardazzi et al.
Folia microbiologica, 49(5), 534-538 (2005-02-11)
Two new plasmids, pEC3 and pECkan, were constructed and their use in yeast transformation described. Both plasmids are derivative of the pRS416 vector, in which the URA3 auxotrophic marker was replaced by the LEU4* gene (pEC3) or the kanMX4 gene
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