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A2636

Sigma-Aldrich

S-(2-Aminoethyl)-L-cysteine hydrochloride

≥98% (TLC)

Synonym(s):

L-4-Thialysine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C5H12N2O2S · HCl
CAS Number:
4099-35-8
Molecular Weight:
200.69
Beilstein:
3697262
EC Number:
223-862-1
MDL number:
MFCD00036385
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24890680
NACRES:
NA.26

Quality Level

200

Assay

≥98% (TLC)

form

powder

color

white to off-white

storage temp.

2-8°C

SMILES string

Cl.NCCSC[C@H](N)C(O)=O

InChI

1S/C5H12N2O2S.ClH/c6-1-2-10-3-4(7)5(8)9;/h4H,1-3,6-7H2,(H,8,9);1H/t4-;/m0./s1

InChI key

CVHKULVNPGAEQM-WCCKRBBISA-N

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Biochem/physiol Actions

S-(2-Aminoethyl)-L-cysteine (AEC) hydrochloride is used as a lysine analogue for comparative analysis with other lysine analogues. S-(2-Aminoethyl)-L-cysteine is an alternative substrate useful for characterizing lysine cyclodeaminase from Streptomyces pristinaespiralis. AEC may be used as a non-antibiotic selection agent for genetically engineered soybeans expressing a lysine insensitive DHPS gene. AEC is being studied as an amino acid antibiotic.

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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Asri Peni Wulandari et al.
FEBS letters, 522(1-3), 35-40 (2002-07-04)
In Thermus thermophilus homocitrate synthase (HCS) catalyzes the initial reaction of lysine biosynthesis through alpha-aminoadipic acid, synthesis of homocitrate from 2-oxoglutarate and acetyl-CoA. HCS is strongly inhibited by lysine, indicating that the biosynthesis is regulated by the endproduct at the
M N Cahyanto et al.
Journal of applied microbiology, 102(3), 674-679 (2007-02-21)
To enhance L-lysine secretion in Lactobacillus plantarum. An S-2-aminoethyl-L-cystein (AEC)-resistant mutant of L. plantarum was isolated, and it produced L-lysine at considerably higher level than the parent strain. Aspartokinase in the mutant has been desensitized to feedback inhibition by L-lysine.
Dasantila Golemi-Kotra et al.
The Journal of biological chemistry, 279(33), 34665-34673 (2004-05-21)
Beta-lactamases and penicillin-binding proteins are bacterial enzymes involved in antibiotic resistance to beta-lactam antibiotics and biosynthetic assembly of cell wall, respectively. Members of these large families of enzymes all experience acylation by their respective substrates at an active site serine
Amarendra N Maity et al.
The journal of physical chemistry. B, 113(36), 12161-12163 (2009-08-19)
We demonstrate that the steady state reaction of lysine 5,6-aminomutase with substrate analogue 4-thia-l-lysine generates a radical intermediate, which accumulates in the enzyme to an electron paramagnetic resonance (EPR) detectable level. EPR line width narrowing of approximately 1 mT due
Do Youn Jun et al.
Biochemical pharmacology, 66(12), 2291-2300 (2003-11-26)
We first report the mechanism for the inhibitory effect of the lysine analog, thialysine on human acute leukemia Jurkat T cells. When Jurkat T cells were treated with thialysine (0.32-2.5 mM), apoptotic cell death along with several biochemical events such
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