Boc-L-glutamic acid γ-benzyl ester is a protected derivative of the amino acid L-glutamic acid in which the α-amino group is masked as a Boc (tert-butoxycarbonyl) carbamate and the γ-carboxyl group is esterified as a benzyl ester. The molecule therefore contains a Boc-protected amine, a free α-carboxylic acid, and a benzyl-protected γ-carboxyl functionality, with the side chain bearing a methylene-linked carboxylate ester that reflects glutamate's acidic character while controlling chemoselectivity. In peptide and amino acid derivative synthesis, this orthogonally protected glutamate analogue is used as a precursor for stepwise incorporation of glutamic acid residues under conditions that distinguish between the free and protected carboxyl groups, supporting the preparation of peptides and related conjugates with controlled side-chain functionality.
CAT No: CP00714
CAS No:13574-13-5
Synonyms/Alias:Boc-Glu(OBzl)-OH;13574-13-5;Boc-L-Glutamicacid5-benzylester;N-alpha-tert-BOC-L-glutamic-gamma-benzylester;5-BenzylN-Boc-L-glutamate;AJDUMMXHVCMISJ-ZDUSSCGKSA-N;SBB063750;L-Glutamicacid,N-[(1,1-dimethylethoxy)carbonyl]-,5-(phenylmethyl)ester;N-(tert-Butoxycarbonyl)-L-glutamicAcid5-BenzylEster;5-BenzylN-(tert-Butoxycarbonyl)-L-glutamate;(s)-5-(benzyloxy)-2-(tert-butoxycarbonylamino)-5-oxopentanoicacid;(2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoicacid;L-Glutamicacid,N-((1,1-dimethylethoxy)carbonyl)-,5-(phenylmethyl)ester;(2S)-2-[(tert-butoxy)carbonylamino]-4-[benzyloxycarbonyl]butanoicacid;N-((1,1-Dimethylethoxy)carbonyl)-L-glutamicacid,5-(phenylmethyl)ester;N-[(1,1-Dimethylethoxy)carbonyl]-L-glutamicacid,5-(phenylmethyl)ester;boc-l-glutamicacidgamma-benzylester;boc-glu(obzl);boc-l-glu(obzl)-oh;N-alpha-t-BOC-L-glutamic-gamma-benzylester;PubChem12178;AC1Q5XNQ;AC1L35QL;boc-l-glutamicacid(obzl);15418_ALDRICH
Boc-L-glutamic acid γ-benzyl ester is a protected L-glutamate derivative designed for peptide synthesis workflows, featuring a Boc-protected alpha-amino group and a γ-benzyl ester on the side chain. This protection pattern stabilizes both the backbone functionality and the glutamate side-chain carboxyl during coupling and assembly steps, enabling controlled formation of glutamate-containing sequences. As a protected amino acid building block, it is commonly selected when side-chain esterification is required to prevent undesired side reactions while maintaining compatibility with standard peptide assembly strategies.
1. Solid-Phase Peptide Synthesis
Boc-L-glutamic acid γ-benzyl ester is used as a glutamate building block for solid-phase peptide synthesis (SPPS) where the Boc group protects the alpha-amino functionality and the γ-benzyl ester masks the side-chain carboxyl. Peptide synthesis teams rely on this configuration to incorporate glutamate residues into linear peptides while minimizing side-chain reactivity during iterative coupling cycles. The benzyl ester side-chain protection is particularly useful when subsequent peptide handling requires the glutamate side chain to remain inert until a later deprotection step, supporting workflows that require clean sequence assembly before final global processing.
2. Protected Glutamate Building Blocks
Boc-L-glutamic acid γ-benzyl ester is frequently selected by peptide chemistry groups and custom peptide manufacturers as a protected glutamate intermediate for segment condensation and modified peptide assembly. The Boc/γ-benzyl protection scheme provides orthogonal control over functional groups during intermediate preparation, allowing developers to manage when the alpha-amino group is unveiled for coupling and when the side-chain carboxyl is ultimately liberated for downstream transformations. This makes the reagent a practical choice for preparing glutamate-containing peptide segments that must remain chemically stable through purification and handling prior to final deprotection and conversion to the free acid form.
3. Glutamate Side-Chain Masking
Boc-L-glutamic acid γ-benzyl ester supports peptide and peptidomimetic development programs that require temporary side-chain masking of the glutamate γ-carboxyl to suppress side reactions such as undesired esterification or cross-reactivity during synthesis. By keeping the side-chain as a benzyl ester during assembly, researchers can focus on constructing the desired backbone connectivity and then address side-chain deprotection as part of the final processing strategy. This approach is commonly used when glutamate residues are positioned in sequences where maintaining side-chain integrity through multiple synthetic operations is essential for reproducible product profiles and efficient downstream purification.
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