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364460

L-Proline benzyl ester hydrochloride

Name: <SC>L</SC>-Proline benzyl ester hydrochloride
Brand: ALDRICH

98%

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₅NO₂ · HCl

CAS Number:

16652-71-4

Molecular Weight:

241.71

NACRES:

NA.22

PubChem Substance ID:

24862432

eCl@ss:

32160406

UNSPSC Code:

12352209

EC Number:

240-700-5

MDL number:

MFCD00039002

Beilstein/REAXYS Number:

3598081

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Properties

Quality Level

100

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

Description

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)

Convenient synthesis of L-proline benzyl ester.

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.

Prolyl aminopeptidase from Streptomyces thermoluteus subsp. fuscus strain NBRC14270 and synthesis of proline-containing peptides by its S144C variant.

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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Global Trade Item Number

SKU	GTIN
364460-5G	04061832641997