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482609

Sigma-Aldrich

N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine

97%

Synonym(s):

([2S,3R]-3-Amino-2-hydroxy-4-phenylbutanoyl)-L-leucine

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About This Item

Linear Formula:
(CH3)2CHCH2CH[NHCOCH(OH)CH(NH2)CH2C6H5]CO2H
CAS Number:
58970-76-6
Molecular Weight:
308.37
EC Number:
261-529-2
MDL number:
MFCD00083262
UNSPSC Code:
12352209
PubChem Substance ID:
24871835
NACRES:
NA.22

Assay

97%

form

powder or crystals

optical activity

[α]20/D −11°, c = 1 in 1 M NaOH

reaction suitability

reaction type: solution phase peptide synthesis

mp

245 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

CC(C)C[C@H](NC(=O)[C@@H](O)[C@H](N)Cc1ccccc1)C(O)=O

InChI

1S/C16H24N2O4/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22)/t12-,13+,14+/m1/s1

InChI key

VGGGPCQERPFHOB-RDBSUJKOSA-N

Gene Information

human ... ANPEP(290) , DPP4(1803)
mouse ... Rnpep(215615)
rat ... Mme(24590)

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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Arun Kumar Singh et al.
International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases, 16(5), e375-e381 (2012-03-14)
Staphylococcus aureus has emerged as a major drug-resistant pathogen in hospital- and community-acquired infections. Leucine aminopeptidase (LAP) is known to be essential for survival of the bacteria; however the LAP of S. aureus has not been extensively characterized. In this
Jung-Mi Kang et al.
Molecular and biochemical parasitology, 182(1-2), 17-26 (2011-12-14)
Leucine aminopeptidases (LAP; EC 3.4.11.1) are a group of metalloexopeptidases, which catalyze the sequential removal of leucine amino acids from the N-termini of the polypeptides or proteins. In this study, we identified two novel genes that encode LAPs of Clonorchis
Xiaopan Zhang et al.
Journal of enzyme inhibition and medicinal chemistry, 28(3), 545-551 (2012-03-03)
Aminopeptidase N (APN/CD13) over expressed on tumour cells, plays a critical role in tumour invasion, metastasis and tumour angiogenesis. In this article, we described the design, synthesis and preliminary activity studies of novel 3-amino-2-hydroxyl-3-phenylpropanoic acid derivatives as APN inhibitors. The
Daniela P Alves et al.
Pharmacology, 89(1-2), 22-28 (2012-01-13)
The aim of the present study was to investigate the mechanisms underlying the endogenous control of nociception at a peripheral level during inflammation. Using a pharmacological approach and the rat paw pressure test, we assessed the effect of an intraplantar
M Lis et al.
Polish journal of veterinary sciences, 14(3), 393-403 (2011-10-01)
Bestatin, a low-molecular weight dipeptide, is a potent inhibitor of aminopeptidase N which has been demonstrated to have antitumor and immunomodulatory effects. The effects of bestatin (10, 1 and 0.1 mg/kg) administered intraperitoneally once, five or ten times to mice
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