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Merck

91917

Sigma-Aldrich

5,5,5-Trifluoro-DL-leucine

≥98.0% (sum of isomers, HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C6H10F3NO2
Número de CAS:
Peso molecular:
185.14
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Takahiro Oba et al.
Bioscience, biotechnology, and biochemistry, 70(7), 1776-1779 (2006-07-25)
We characterized a trifluoroleucine-resistant mutant of Saccharomyces cerevisiae, TFL20, that has a mutation in the LEU4 gene. We monitored the concentration of extracellular i-AmOH and intracellular amino acids, and compared the ratios of gene expression in TFL20 with the wild-type
B Bendoni et al.
FEMS microbiology letters, 180(2), 229-233 (1999-11-11)
The resistance to 5,5,5-trifluoro-DL-leucine, encoded by the dominant allele LEU4-1, was used as a selectable marker to transform laboratory and natural Saccharomyces cerevisiae strains by the lithium acetate procedure. Results of transformation of S. cerevisiae laboratory and wine natural strains
E Casalone et al.
Research in microbiology, 148(7), 613-623 (1998-10-10)
Eighteen mutants resistant to 5',5',5'-trifluoroleucine (TFL), a leucine analog, were isolated in Saccharomyces cerevisiae strains YNN281 and YNN282. The mutants were characterized genetically and clustered in two groups, one comprising all the dominant (TFL1) and the other one all the
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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