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49510

Sigma-Aldrich

L-Glutamic acid γ-benzyl ester

≥99.0% (T)

Synonym(s):

L-Glutamic acid 5-benzyl ester

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About This Item

Linear Formula:
C6H5CH2OCOCH2CH2CH(NH2)COOH
CAS Number:
Molecular Weight:
237.25
Beilstein:
1885646
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥99.0% (T)

optical activity

[α]20/D +19±2°, c = 1% in acetic acid

reaction suitability

reaction type: solution phase peptide synthesis

mp

181-182 °C (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

N[C@@H](CCC(=O)OCc1ccccc1)C(O)=O

InChI

1S/C12H15NO4/c13-10(12(15)16)6-7-11(14)17-8-9-4-2-1-3-5-9/h1-5,10H,6-8,13H2,(H,15,16)/t10-/m0/s1

InChI key

BGGHCRNCRWQABU-JTQLQIEISA-N

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Application

L-Glutamic acid γ-benzyl ester is commonly used in the synthesis of polymers for biological applications. Some of the examples are:
  • Synthesis of bioreducible block copolymers based on poly(ethylene glycol) and poly(γ-benzyl L-glutamate) for Intracellular drug delivery.
  • Synthesis of biodegradable poly(L-glutamic acid)-b-polylactide for magnetic resonance imaging (MRI)-visible drug delivery system.
  • Synthesis of pH and temperature-responsive diblock copolymers based on poly(L-glutamic acid).

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

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Novel pH?and Temperature?Responsive Block Copolymers with Tunable pH?Responsive Range.
He C, et al.
Macromolecular Rapid Communications, 29(6), 490-497 (2008)
Bioreducible block copolymers based on poly (ethylene glycol) and poly (γ-benzyl L-glutamate) for intracellular delivery of camptothecin.
Thambi T, et al.
Bioconjugate Chemistry, 22(10), 1924-1931 (2011)
Near-infrared light sensitive polypeptide block copolymer micelles for drug delivery.
Kumar S, et al.
Journal of Materials Chemistry, 22(15), 7252-7257 (2012)
Micelles Based on Biodegradable Poly (l-glutamic acid)-b-Polylactide with Paramagnetic Gd Ions Chelated to the Shell Layer as a Potential Nanoscale MRI? Visible Delivery System.
Zhang G, et al.
Biomacromolecules, 9(1), 36-42 (2007)
Self-assembly of rod? coil diblock oligomers based on α-helical peptides.
Lecommandoux S, et al.
Macromolecules, 34(26), 9100-9111 (2001)

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