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C8601

Sigma-Aldrich

Z-Pro-OH

99%

Synonym(s):

Z-L-Proline

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About This Item

Empirical Formula (Hill Notation):
C13H15NO4
CAS Number:
1148-11-4
Molecular Weight:
249.26
Beilstein/REAXYS Number:
88579
EC Number:
214-557-4
MDL number:
MFCD00003170
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24893080
NACRES:
NA.22

assay

99%

form

powder or crystals

optical activity

[α]20/D −42°, c = 2 in ethanol

reaction suitability

reaction type: solution phase peptide synthesis

technique(s)

NMR: suitable

color

white

mp

76-78 °C (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)[C@@H]1CCCN1C(=O)OCc2ccccc2

InChI

1S/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m0/s1

InChI key

JXGVXCZADZNAMJ-NSHDSACASA-N

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Application

Z-Pro-OH can be used:
  • As a starting material to prepare aib-pro endothiopeptides of pharmacological importance.
  • To prepare biologically significant fluorophore-labeled peptide tetramers or dimers.
  • As a reactant to synthesize benzoxazole derived human neutrophil elastase (HNE) inhibitors.

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)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH2726
BCCC6213
BCCB4986
BCBT8771
BCBQ3200V

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Design and synthesis of peptide-based carboxylic acid-containing transition-state inhibitors of human neutrophil elastase
Sato F, et al.
Bioorganic & medicinal chemistry letters, 12(4), 551-555 (2002)
A new dendrimer scaffold for preparing dimers or tetramers of biologically active molecules
Raju N, et al.
Tetrahedron Letters, 46(9), 1463-1465 (2005)
The `azirine/oxazolone approach?to the synthesis of Aib-Pro endothiopeptides
Budzowski A, et al.
Helvetica Chimica Acta, 91(8), 1471-1488 (2008)
Cytotoxicity of carbobenzoxy-protected amino acids.
M Dolenga et al.
In vitro cellular & developmental biology : journal of the Tissue Culture Association, 28A(5), 300-302 (1992-05-01)
Sachin Mittal et al.
Pharmaceutical research, 24(7), 1290-1298 (2007-03-23)
To determine the bioactivation and uptake of prolidase-targeted proline prodrugs of melphalan in six cancer cell lines with variable prolidase expression and to evaluate prolidase-dependence of prodrug cytotoxicity in the cell lines compared to that of the parent drug, melphalan.
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