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L8397

Sigma-Aldrich

ʟ-Leucinethiol

leucine aminopeptidase inhibitor, solid

Synonym(s):

Dithiobis(2-amino-4-methylpentane)

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About This Item

Empirical Formula (Hill Notation):
C12H28N2S2 · 2HCl
CAS Number:
88264-65-7
Molecular Weight:
337.42
MDL number:
MFCD00133441
UNSPSC Code:
12352202
PubChem Substance ID:
24278518
NACRES:
NA.77

product name

L-Leucinethiol, oxidized dihydrochloride, leucine aminopeptidase inhibitor

Quality Level

200

form

solid

storage temp.

−20°C

SMILES string

CC(C)C[C@H](N)CS

InChI

1S/C6H15NS/c1-5(2)3-6(7)4-8/h5-6,8H,3-4,7H2,1-2H3/t6-/m0/s1

InChI key

GXEDNWSUKCJLLB-LURJTMIESA-N

Application

Upon reduction in vivo to L-leucinethiol, compound is a potent inhibitor of leucine aminopeptidase.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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W W Chan
Biochemical and biophysical research communications, 116(1), 297-302 (1983-10-14)
L-leucinthiol (2-amino-4-methyl-1-pentanethiol) was designed as an inhibitor of leucine aminopeptidase by analogy with sulfhydryl inhibitors of other zinc-containing peptidases. It was synthesized from L-leucinol and shown to be a potent competitive inhibitor of the microsomal aminopeptidase from porcine kidney (Ki
T D Ocain et al.
Biochemical and biophysical research communications, 145(3), 1038-1042 (1987-06-30)
L-Lysinethiol was found to be an extremely potent inhibitor of aminopeptidase B (AP-B) with a Ki = 9.1 X 10(-10) M. L-leucinethiol was also a potent inhibitor of AP-B (kj = 1.3 X 10(-7) M), while the D-isomer was much
D S Pickering et al.
Archives of biochemistry and biophysics, 239(2), 368-374 (1985-06-01)
L-Leucinthiol, a synthetic derivative of mercaptoethylamine with a hydrophobic side chain, was recently reported to be a potent inhibitor of microsomal aminopeptidase. The structural features necessary for interaction of mercaptoamines with this enzyme have now been explored more systematically. Optimal
Kathrin Textoris-Taube et al.
European journal of immunology, 50(2), 270-283 (2019-11-16)
Dissecting the different steps of the processing and presentation of tumor-associated antigens is a key aspect of immunotherapies enabling to tackle the immune response evasion attempts of cancer cells. The immunodominant glycoprotein gp100209-217 epitope, which is liberated from the melanoma
T D Ocain et al.
Journal of medicinal chemistry, 31(11), 2193-2199 (1988-11-01)
Sulfur-containing amino acid and peptide analogues of bestatin [((2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoyl)-L-leucine] (1) have been synthesized and evaluated as inhibitors of aminopeptidase M (AP-M), leucine aminopeptidase (LAP), and aminopeptidase B (AP-B). The 2-thiolbestatin analogue (6) was found to be a potent inhibitor of
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