Boc-L-Hse(Bzl)-OH is a Boc-protected, benzyl-substituted amino acid derivative in which the amino acid backbone is present as a protected L-configured residue and the side chain corresponds to homoserine bearing a benzyl ether substituent. The molecule contains a Boc carbamate protecting group on the amino functionality and a benzyl-protected hydroxyl group on the side chain, while the carboxyl group remains available for coupling chemistry as a free carboxylic acid. In peptide and amino acid derivative synthesis, this protected analogue is used as a stepwise building block to control chemoselectivity by masking both the amine and the side-chain alcohol, supporting incorporation into protected peptide frameworks and enabling downstream deprotection and functionalization of the side-chain hydroxyl.
CAT No: CP25919
CAS No:59408-74-1
Synonyms/Alias:Boc-Glu(OBzl)-OMe;59279-58-2;(S)-5-Benzyl1-methyl2-((tert-butoxycarbonyl)amino)pentanedioate;BOC-GLU-OME;SCHEMBL2301376;KHCZTGSAKNZBOV-AWEZNQCLSA-N;MolPort-023-330-886;ZINC2556542;8817AB;AKOS016002058;AJ-39925;AK-49960;AB0072735;FT-0689477;ST24036218;J-300096;Q-101684;5-benzyl1-methyl(2S)-2-{[(tert-butoxy)carbonyl]amino}pentanedioate;(S)-2-tert-Butoxycarbonylamino-pentanedioicacid5-benzylester1-methylester
Chemical Name:N-alpha-t-Butyloxycarbonyl-O-benzyl-L-homoserine
Boc-L-Hse(Bzl)-OH is a Boc-protected L-amino acid derivative bearing a benzyl-protected side chain on homoserine (Hse), providing a protected, carboxyl-activated building block format commonly used in peptide chemistry. The Boc group supports controlled N-terminus protection during stepwise assembly, while the benzyl side-chain protection helps preserve the hydroxyl functionality through coupling and deprotection steps. This protected amino acid is therefore positioned as a reliable intermediate for generating defined peptide sequences that require homoserine-derived functionality with minimal side reactions.
1. Solid-Phase Peptide Synthesis
Boc-L-Hse(Bzl)-OH is used by peptide synthesis groups performing solid-phase peptide synthesis to introduce homoserine residues into peptide chains while maintaining orthogonal protection of the side-chain hydroxyl. The Boc-protected amino functionality supports routine segment coupling workflows, and the benzyl-protected side chain helps prevent premature side-chain reactivity during peptide elongation. Research laboratories and custom peptide manufacturers select this specific protection pattern when the downstream target requires a homoserine-derived hydroxyl handle to be revealed at a later stage for further derivatization or for generating peptides with controlled functional-group density.
2. Side-Chain Functional Peptide Intermediates
Boc-L-Hse(Bzl)-OH is commonly employed to prepare peptide intermediates used for subsequent chemical modification of the homoserine side chain. After peptide assembly, the benzyl-protected hydroxyl can be unmasked to enable downstream steps such as conversion to protected or activated hydroxyl derivatives, attachment of linkers, or incorporation into chemical biology constructs where the position and availability of the alcohol group are critical. This makes the reagent valuable for teams developing site-specific peptide derivatives, including groups building peptide conjugates or preparing defined peptide standards that require precise control over functional-group exposure.
3. Pharmaceutical Intermediate Development
Boc-L-Hse(Bzl)-OH is also used in pharmaceutical intermediate development where homoserine-containing fragments must be assembled with reliable protection of both the amino terminus and the side-chain hydroxyl. Medicinal chemistry and process-development teams often rely on protected amino acid building blocks to generate well-defined intermediates for larger synthetic sequences, including routes that require later functional-group unveiling without disturbing other sensitive moieties. The Boc/benzyl protection strategy supports predictable handling during multistep synthesis, making this derivative a practical choice when homoserine-derived functionality must be introduced early and revealed or transformed only at a controlled downstream stage.
4. Peptide Library and SAR Building Blocks
Boc-L-Hse(Bzl)-OH is used by peptide library and structure-activity relationship (SAR) chemistry teams to generate series of peptides that vary around a homoserine-containing motif while keeping the side-chain hydroxyl protected during library synthesis. By standardizing the protection pattern at the homoserine position, researchers can focus variation on other residues or modifications while maintaining consistent reactivity control across the library. This approach is particularly useful for teams producing multiple analogs for screening workflows, where uniform protection during synthesis reduces variability arising from side reactions and supports streamlined downstream deprotection and functionalization steps.
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