Skip to Content
Merck
All Photos(1)

Key Documents

More Documents

90182

Sigma-Aldrich

Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride

≥99.0% (AT)

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

Looking for similar products? Visit Product Comparison Guide

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.

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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.
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
I Kourteva et al.
Analytical biochemistry, 162(2), 345-349 (1987-05-01)
A technique for quickly detecting nanogram quantities of low- and high-molecular-weight inhibitors of some serine proteases is described. The inhibitor solutions are spotted onto agar films which contain either L-1-p-tosylamino-2-phenylethyl chloromethyl ketone (TPCK)-trypsin or tosyl lysine chloromethyl ketone (TLCK)-chymotrypsin. Enzyme
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service