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364460

Sigma-Aldrich

L-Proline benzyl ester hydrochloride

98%

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About This Item

Empirical Formula (Hill Notation):
C12H15NO2 · HCl
CAS Number:
16652-71-4
Molecular Weight:
241.71
Beilstein:
3598081
EC Number:
240-700-5
MDL number:
MFCD00039002
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24862432
NACRES:
NA.22

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

SMILES string

Cl[H].[H][C@]1(CCCN1)C(=O)OCc2ccccc2

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

InChI key

NEDMOHHWRPHBAL-MERQFXBCSA-N

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Application

Extensive applications in peptide chemistry and used as a chiral auxiliary in the asymmetric Diels-Alder reaction.

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)

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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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)
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
Aldrichimica Acta, 23, 45-45 (1990)

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