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C8601

Sigma-Aldrich

Z-Pro-OH

99%

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

Quality Level

200

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.

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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A new dendrimer scaffold for preparing dimers or tetramers of biologically active molecules
Raju N, et al.
Tetrahedron Letters, 46(9), 1463-1465 (2005)
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)
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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