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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)

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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
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
Yanna Zhu et al.
Peptides, 33(2), 265-271 (2012-01-26)
Bestatin, a dipeptide, a low molecular weight aminopeptidase inhibitor, has been demonstrated to be an immunomodulator with an antitumor activity. However, the transporter-mediated renal excretion of bestatin is not fully understood. The purpose of this study was to elucidate the
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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
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