Boc-Glu-OEt · DCHA is a protected glutamic acid derivative featuring a Boc-protected α-amino group and an ethyl ester at the α-carboxyl position, with the side chain retaining the γ-carboxyl functionality characteristic of glutamate. The molecule is present as a dicyclohexylamine (DCHA) salt, which is associated with the deprotonated carboxylate form and supports handling and solubility for the esterified amino acid intermediate. In peptide and amino-acid derivative synthesis, it functions as a stepwise building block that allows controlled coupling at the protected α-amino/activated carboxyl ends while the γ-carboxyl group remains available for subsequent derivatization or protection strategies.
CAT No: CP27548
CAS No:86938-17-2
Synonyms/Alias:(S)-4-((tert-Butoxycarbonyl)amino)-5-ethoxy-5-oxopentanoicacid;86938-17-2;SCHEMBL2301394;LXQBXYDPJVHNPQ-QMMMGPOBSA-N;MolPort-027-948-644;ZINC71788053;AKOS016014248;AK129002;AJ-118548;KB-211503;FT-0699100;(S)-2-tert-butoxycarbonylamino-pentanedioicacid1-ethylester
Boc-Glu-OEt · DCHA is a protected glutamate building block featuring a Boc-protected amino group and an ethyl ester at the side-chain carboxylate, supplied as a dicyclohexylamine (DCHA) salt to improve handling and crystallinity for synthetic workflows. This protected amino acid derivative is designed for downstream peptide assembly where glutamate's side-chain functionality must be masked during coupling and later revealed as part of controlled peptide fragment construction. Researchers and custom synthesis groups commonly use this form to enable reliable segment condensation and to manage solubility and reactivity during protected-amino-acid chemistry.
1. Solid-Phase Peptide Synthesis
Boc-Glu-OEt · DCHA is used as a glutamate-containing residue precursor in protected-amino-acid workflows that require the side-chain carboxyl group to remain esterified during assembly. Peptide synthesis teams and contract peptide manufacturers select this derivative when they want a defined glutamate side-chain protection pattern that survives coupling steps and supports consistent fragment assembly. The Boc group provides an N-protection strategy compatible with standard peptide synthesis planning, while the ethyl ester helps maintain the glutamate side chain in a non-carboxylate state during early stages of chain elongation.
2. Solution-Phase Segment Coupling
Boc-Glu-OEt · DCHA is frequently incorporated into solution-phase peptide synthesis and segment condensation strategies where protected glutamate residues are needed as stable intermediates for coupling. Medicinal chemistry groups and peptide process development scientists use this protected amino acid to control functional group exposure across multi-step assembly, especially when preparing longer peptide fragments or complex sequences that require careful orthogonal protection planning. The DCHA salt form supports practical weighing, transfer, and reproducible reactivity in batch coupling workflows, which is valuable for iterative synthesis and scale-up of peptide intermediates.
3. Glutamate-Containing Peptide Intermediates
Boc-Glu-OEt · DCHA serves as a practical intermediate for generating glutamate-bearing peptide building blocks used in downstream derivatization and purification workflows. Peptide chemists preparing libraries of protected fragments or performing late-stage modifications often rely on this specific protection pattern to keep the glutamate side chain masked until the appropriate deprotection window. Because the product is already in a protected, esterified glutamate form, it integrates directly into fragment-based synthesis routes used to construct peptide targets with controlled side-chain chemistry and predictable handling characteristics during intermediate isolation.
4. Pharmaceutical Intermediate Development
Boc-Glu-OEt · DCHA is also used in the development of peptide-based pharmaceutical intermediates where glutamate residues must be introduced as well-defined, protected units. Process chemistry teams and custom synthesis providers incorporate this derivative into routes that build peptide motifs for lead optimization, SAR studies, and advanced intermediate preparation. The combination of Boc protection and an esterified side chain supports controlled functional group management across manufacturing-like workflows, helping ensure that glutamate's reactivity is deferred until the sequence design calls for side-chain unveiling and subsequent downstream transformations.
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