gamma-Benzyl L-glutamate, CAS No. 1676-73-9

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1676-73-9

Catalog No. EBD4664

CAS 1676-73-9

Name gamma-Benzyl L-glutamate

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Basic Information

Synonyms: d-glutamicacid5-benzylester l-glutamicacid,5-(phenylmethyl)ester glutamicacid(obzl)-oh glutamicacid-gamma-benzylester h-l-glu(obzl)-oh h-l-glu(bzl)-oh h-glu(obzl)-oh glu(obzl) 1-(4-Ethoxyphenyl)ethan-1-one gamma-BenzylL-glutamate Gamma-benzyl-L-glutamate L-GLUTAMICACID-5-BENZYLESTER L-glutamicacidgamma-benzylester 2-amino-5-(benzyloxy)-5-oxopentanoicacid(non-preferredname) (2S)-2-amino-5-(benzyloxy)-5-oxopentanoicacid(non-preferredname) (2S,4R)-2-ammonio-4-benzylpentanedioate L-Glutamicacid5-benzylester 2-amino-5-(benzyloxy)-5-oxopentanoicacid(n

Molecular Formula: C12H15NO4

Molecular Weight: 237.25

MDL Number: MFCD00002633

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Other Pharmaceutical Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives

Product Description:

L-Glutamic acid γ-benzyl ester is a protected derivative of the natural amino acid L-glutamic acid, where the γ-carboxylic acid group is esterified with benzyl alcohol. It is a white to off-white crystalline powder. This compound is a crucial building block in peptide synthesis, particularly for solid-phase peptide synthesis (SPPS) using the Fmoc strategy. The benzyl ester (OBzl) protecting group on the glutamic acid side chain is stable under the basic conditions used for Fmoc deprotection but can be readily removed under strong acidic conditions (e.g., hydrogen fluoride or trifluoromethanesulfonic acid) during final cleavage from the resin. Its primary application is as a key intermediate in the pharmaceutical and biotechnology industries for the synthesis of peptides and peptidomimetics. It is extensively used to incorporate glutamic acid residues into peptide sequences where the side-chain carboxyl group needs to be protected during assembly and later deprotected or further functionalized. Peptides containing glutamic acid are important in various therapeutic areas, including hormone analogs, enzyme inhibitors, and vaccine development.

Physical Properties

Melting Point: 181-182 °C(lit.)

Boiling Point: 426.1 °C at 760 mmHg

Flash Point: 211.5 °C

Density: 1.245 g/cm3

Storage: 2-8°C

Analytical Data

Appearance: white powder