364460
L-Proline benzyl ester hydrochloride
98%
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About This Item
Empirical Formula (Hill Notation):
C12H15NO2 · HCl
CAS Number:
Molecular Weight:
241.71
NACRES:
NA.22
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
240-700-5
MDL number:
Beilstein/REAXYS Number:
3598081
InChI key
NEDMOHHWRPHBAL-MERQFXBCSA-N
InChI
1S/C12H15NO2.ClH/c14-12(11-7-4-8-13-11)15-9-10-5-2-1-3-6-10;/h1-3,5-6,11,13H,4,7-9H2;1H/t11-;/m0./s1
SMILES string
Cl[H].[H][C@]1(CCCN1)C(=O)OCc2ccccc2
assay
98%
optical activity
[α]20/D −48°, c = 1 in H2O
reaction suitability
reaction type: solution phase peptide synthesis
mp
148-151 °C (lit.)
application(s)
peptide synthesis
Quality Level
Application
Extensive applications in peptide chemistry and used as a chiral auxiliary in the asymmetric Diels-Alder reaction.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Enantiomeric purity determination of L-proline benzyl ester by chiral column gas chromatography.
M Jemal et al.
Journal of chromatography, 392, 442-446 (1987-04-17)
Aldrichimica Acta, 23, 45-45 (1990)
A Córdova et al.
Bioorganic & medicinal chemistry letters, 9(21), 3119-3122 (1999-11-24)
Mesylates or tosylates of delta-hydroxy-L-norvaline esters spontaneously afford L-proline esters upon exposure to aqueous buffer in near quantitative yield. This novel reaction has led to the development of a simple route to optically active proline esters.
Yukihiro Yamamoto et al.
Applied and environmental microbiology, 76(18), 6180-6185 (2010-08-03)
We specifically examined an exopeptidase, prolyl aminopeptidase (PAP), as a target for synthesis of proline-containing peptides. A PAP from Streptomyces thermoluteus subsp. fuscus NBRC14270 (PAP14270) was obtained using sequence-based screening. From PAP14270, 144Ser was replaced by Cys (scPAP14270) to give
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