(Boc)2-4-GPAc-OH is a protected amino acid derivative featuring a 4-substituted glycine scaffold bearing an acylated side-chain functionality and two tert-butoxycarbonyl (Boc) protecting groups on amino-derived sites. The molecule contains carboxylic acid and protected amine functionalities, with the Boc groups serving as carbamate protecting groups that suppress undesired amine reactivity during stepwise coupling chemistry. It is used as a building block in amino acid and peptide synthesis workflows where controlled chemoselectivity, protection of amino functionality, and incorporation of the substituted, acyl-bearing side chain into larger peptide or peptidomimetic structures are required.
CAT No: CP25254
CAS No:1263045-12-0
Synonyms/Alias:4-[(Boc)2-guanidino]phenylacetic acid
Chemical Name:4-[Bis(t-butyloxycarbonyl)-guanidino]phenylacetic acid
(Boc)2-4-GPAc-OH is a Boc-protected amino acid derivative featuring a glycine-like backbone bearing an acylated side-chain functionality, supplied as a protected intermediate suitable for downstream peptide and building-block synthesis. The presence of Boc protecting groups and the acylated side-chain motif make it a practical precursor for assembling protected peptide fragments where controlled deprotection and coupling are required. Researchers in peptide chemistry and pharmaceutical intermediate development use this type of protected amino acid derivative to build defined structures while maintaining functional-group compatibility during multistep synthesis.
1. Protected Peptide Fragment Building
(Boc)2-4-GPAc-OH is used as a protected amino acid building block for constructing defined peptide segments in both research-scale and custom peptide synthesis workflows. The Boc-protected functionality supports stepwise assembly strategies where the amino and/or side-chain reactive positions must remain masked during coupling, helping maintain structural fidelity in multicomponent sequences. Peptide chemists commonly select this derivative when a specific protected side-chain environment is needed to control chemoselectivity across fragment condensation and subsequent deprotection steps.
2. Pharmaceutical Intermediate Synthesis
(Boc)2-4-GPAc-OH serves as a protected intermediate for medicinal chemistry and process development programs that require amino-acid-derived scaffolds with controlled functional-group presentation. In this context, the derivative is used to access downstream intermediates that retain protection during early synthetic elaboration, enabling later conversion to target-facing functional groups under conditions compatible with other sensitive motifs in the molecule. Pharmaceutical intermediate developers value Boc-protected amino acid derivatives as modular inputs that can be incorporated into larger synthetic routes while reducing side reactions from unprotected amine functionality.
3. Orthogonally Protected Derivative Preparation
(Boc)2-4-GPAc-OH is applied in the preparation of further protected derivatives where maintaining protected amine character is essential for selective transformations later in the sequence. Synthetic chemistry groups use this type of Boc-protected amino acid derivative to generate intermediate libraries or to tailor protecting-group patterns before final coupling or functional-group unveiling. The acylated side-chain feature also supports downstream derivatization strategies aimed at tuning reactivity and handling properties of the resulting amino acid-derived fragments.
4. Solid-Phase Peptide Scheme Development
(Boc)2-4-GPAc-OH is leveraged in peptide synthesis planning when a protected amino acid derivative is needed to integrate a specific residue environment into a larger sequence assembled under protected-group conditions. Peptide development teams use such intermediates to evaluate coupling compatibility and to define the protecting-group logic required for the intended synthesis route, including how the protected amine functionality will behave during deprotection and subsequent residue additions. This makes the compound a useful input during method development for assembling peptide targets that require careful control of functional-group exposure throughout the synthesis cycle.
1. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
4. Urinary Metabolites Associated with Blood Pressure on a Low-or High-Sodium Die
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