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Merck

G3267

Sigma-Aldrich

Glycine benzyl ester hydrochloride

≥98% (TLC)

Sinónimos:

Benzyl glycinate

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About This Item

Fórmula empírica (notación de Hill):
C9H11NO2 · HCl
Número de CAS:
Peso molecular:
201.65
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

product name

Glycine benzyl ester hydrochloride,

assay

≥98% (TLC)

Quality Level

form

powder

color

white

storage temp.

−20°C

SMILES string

Cl.NCC(=O)OCc1ccccc1

InChI

1S/C9H11NO2.ClH/c10-6-9(11)12-7-8-4-2-1-3-5-8;/h1-5H,6-7,10H2;1H

InChI key

VLQHNAMRWPQWNK-UHFFFAOYSA-N

Application

Glycine benzyl ester is used as an organic reagent in condensing reactions.

Biochem/physiol Actions

The benzyl ester group of the amino acid monomers promote kinetically controlled synthesis (KCS) of polypeptides by increasing the substrate affinity and specificity of the enzyme. It is useful in the chemoenzymatic polymerization of glycine monomers.

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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V Maurich et al.
Farmaco (Societa chimica italiana : 1989), 49(12), 805-808 (1994-12-01)
The synthesis of 2-(4-amino-5-chloro-2-methoxybenzamido)acetic acid 2, a metabolite of metoclopramide 1, has been accomplished through the coupling of 4-amino-5-chloro-2-methoxybenzoic acid 4 with glycine benzyl ester followed by a catalytic hydrogenation. Such a metabolite could not be detected directly in the
J Martinez et al.
Carbohydrate research, 50(1), 15-22 (1976-08-01)
An O-glycodipeptide was synthesized by lengthening the peptide chain on the C-terminal side of a glycosylamino acid unit. N-(Benzyloxycarbonyl)-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-L-threonine o-nitrophenyl ester and pentachlorophenyl ester were condensed with glycine benzyl ester to give both the same glycodipeptide, [N-(benzyloxycarbonyl)-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-L-threonyl]glycine benzyl ester (9).
Jose Manuel Ageitos et al.
Biomacromolecules, 17(1), 314-323 (2015-12-02)
The chemoenzymatic polymerization of amino acid monomers by proteases involves a two-step reaction: the formation of a covalent acyl-intermediate complex between the protease and the carboxyl ester group of the monomer and the subsequent deacylation of the complex by aminolysis

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