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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

Quality Level

100

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCD4914
MKBW9442V
MKBR2220V
MKBK0650V
MKBJ8307V

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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
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
Atsushi Wakita et al.
International journal of hematology, 96(1), 84-93 (2012-05-29)
We conducted a multicenter prospective randomized study to compare a fixed-scheduled induction therapy with a response-oriented individualized induction therapy for elderly patients with acute myeloid leukemia (AML). Newly diagnosed AML patients, aged between 65 and 80, were randomly assigned to
Magdalena Lis et al.
Pharmacological reports : PR, 63(6), 1481-1490 (2012-02-24)
The low-molecular weight dipeptide bestatin is a potent inhibitor of aminopeptidase N and has been demonstrated to have antitumor and immunomodulatory effects. The effects of bestatin on interleukin (IL)-1β synthesis and release by peritoneal macrophages stimulated in vitro with lipopolysaccharide
Yekaterina Poloz et al.
Eukaryotic cell, 11(4), 545-557 (2012-02-22)
Bestatin methyl ester (BME) is an inhibitor of Zn(2+)-binding aminopeptidases that inhibits cell proliferation and induces apoptosis in normal and cancer cells. We have used Dictyostelium as a model organism to study the effects of BME. Only two Zn(2+)-binding aminopeptidases
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