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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:
1676-73-9
Molecular Weight:
237.25
Beilstein:
1885646
EC Number:
216-826-1
MDL number:
MFCD00002633
UNSPSC Code:
12352209
PubChem Substance ID:
57651200
NACRES:
NA.22

Quality Level

100

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

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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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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