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G3267

Sigma-Aldrich

Glycine benzyl ester hydrochloride

≥98% (TLC)

Synonym(s):

Benzyl glycinate

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About This Item

Empirical Formula (Hill Notation):
C9H11NO2 · HCl
CAS Number:
Molecular Weight:
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)

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 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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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).
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
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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