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Key Documents

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:
Molecular Weight:
337.42
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

product name

L-Leucinethiol, oxidized dihydrochloride, leucine aminopeptidase inhibitor

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 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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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
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
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

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