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90182

Sigma-Aldrich

Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride

≥99.0% (AT)

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Synonym(s):
(3S)-1-Chloro-3-tosylamido-7-amino-2-heptanone hydrochloride, (3S)-7-Amino-1-chloro-3-tosylamino-2-heptanone hydrochloride, TLCK, Tosyl-L-lysyl-chloromethane hydrochloride
Empirical Formula (Hill Notation):
C14H21ClN2O3S · HCl
CAS Number:
4272-74-6
Molecular Weight:
369.31
Beilstein:
7106867
EC Number:
224-266-4
MDL number:
MFCD00065395
UNSPSC Code:
12352202
eCl@ss:
32160406
PubChem Substance ID:
57653369
NACRES:
NA.77

biological source

synthetic

Quality Level

100

Assay

≥99.0% (AT)

form

powder or crystals

optical activity

[α]20/D −7.8±0.5°, c = 2% in H2O

storage temp.

−20°C

SMILES string

Cl[H].Cc1ccc(cc1)S(=O)(=O)N[C@@H](CCCCN)C(=O)CCl

InChI

1S/C14H21ClN2O3S.ClH/c1-11-5-7-12(8-6-11)21(19,20)17-13(14(18)10-15)4-2-3-9-16;/h5-8,13,17H,2-4,9-10,16H2,1H3;1H/t13-;/m0./s1

InChI key

YFCUZWYIPBUQBD-ZOWNYOTGSA-N

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Other Notes

An alkylating reagent that may react with histidine or cysteine residues at the active site of enzymes. Inactivates serine proteases such as trypsin and clostripain . Chymotrypsin is not affected. To prevent proteolytic degradation, a combination of TLCK and TPCK can be used throughout the isolation of proteins, as in the isolation of histones.

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)

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J M Griscavage et al.
Biochemical and biophysical research communications, 215(2), 721-729 (1995-10-13)
The objective of this study was to ascertain the mechanism by which serine and cysteine proteinase inhibitors interfere with production of NO by LPS-activated rat alveolar macrophages. Macrophages were incubated in the presence of LPS+ test agent for 24 hr.
Further observations on substrate-derived chloromethyl ketones that inactivate trypsin.
E Shaw et al.
Archives of biochemistry and biophysics, 139(2), 298-305 (1970-08-01)
Victor F Zevallos et al.
European journal of nutrition, 58(4), 1507-1514 (2018-03-31)
Wheat amylase trypsin inhibitors (ATI) are dietary non-gluten proteins that activate the toll-like receptor 4 on myeloid cells, promoting intestinal inflammation. We investigated the effects of dietary ATI on experimental allergic airway inflammation. Mice on a gluten and ATI-free diet
Studies on the active site of clostripain. The specific inactivation by the chloromethyl ketone derived from -N-tosyl-L-lysine.
W H Porter et al.
The Journal of biological chemistry, 246(24), 7675-7682 (1971-12-25)
M K Urban et al.
Biochemistry, 18(18), 3952-3960 (1979-09-04)
Chicken erythrocyte histones 2A, 2B, and 3 can be resolved into nonallelic primary structure variants by polyacrylamide gel electrophoresis in the presence of Triton X-100. These variants were isolated and characterized by analysis of their tryptic and thermolytic peptides. The
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