(Boc)2-4-trans-GCHC-OH is a Boc-protected, trans-configured amino acid derivative based on 4-trans-GCHC (a glycine/γ-carboxyl-containing chiral amino acid framework) bearing two tert-butoxycarbonyl (Boc) carbamate protecting groups on the amino functionality. The molecule contains a free carboxylic acid group (-COOH) while the Boc groups mask amine reactivity, and the trans stereochemical descriptor indicates a defined relative configuration within the substituted carbon framework. In peptide chemistry, this protected intermediate is used as a controlled building block for stepwise amide-bond formation, where the Boc-protected amine(s) support chemoselective coupling and the carboxyl group provides the acylating handle for incorporation into larger peptide derivatives.
CAT No: CP25264
CAS No:1263046-44-1
Synonyms/Alias:4-trans-[(Boc)2-guanidino]cyclohexane carboxylic acid
Chemical Name:4-trans-[Bis(t-butyloxycarbonyl)-guanidino]cyclohexane carboxylic acid
(Boc)2-4-trans-GCHC-OH is a Boc-protected, stereodefined amino acid building block featuring the 4-trans configuration of the GCHC side-chain framework and two Boc-protecting groups on the reactive amino functionality. This protected derivative is designed for downstream peptide and peptidomimetic assembly where controlled stereochemistry and orthogonal reactivity are important for building complex amide linkages. In synthetic workflows, the Boc protection pattern supports handling and stepwise coupling strategies commonly used in medicinal chemistry and custom peptide manufacturing.
1. Peptidomimetic Building Blocks
(Boc)2-4-trans-GCHC-OH is used as a stereodefined amino acid building block for constructing peptidomimetic scaffolds and modified peptide analogs in structure-activity relationship (SAR) studies. Medicinal chemistry groups and peptide synthesis service providers rely on this type of protected, configuration-controlled intermediate to introduce a specific side-chain geometry into sequence-defined amide frameworks, enabling systematic variation of backbone/side-chain features during lead optimization. The Boc-protected form supports routine solid- or solution-phase workflows where protected amines are required to prevent side reactions during coupling and purification.
2. Pharmaceutical Intermediate Synthesis
(Boc)2-4-trans-GCHC-OH serves as a practical intermediate for preparing higher-complexity pharmaceutical and agrochemical building blocks that incorporate the GCHC motif. Process development chemists and custom synthesis teams use stereodefined, protected amino acid derivatives to reduce ambiguity in downstream coupling steps and to maintain stereochemical integrity through multi-step assembly. The presence of Boc-protected functionalities makes the compound a convenient input for generating protected peptide fragments, advanced coupling partners, and related amide-containing intermediates used in iterative medicinal chemistry campaigns.
3. Stereocontrolled Amide Coupling
(Boc)2-4-trans-GCHC-OH is applied in stereocontrolled amide bond formation where the 4-trans configuration must be carried through to the final sequence or intermediate. Research groups developing constrained or conformationally biased peptide-like structures often select protected amino acid derivatives to ensure that reactive sites are masked during activation/coupling and that the desired stereochemical outcome is preserved across synthetic steps. This makes the compound useful for generating defined intermediates for subsequent deprotection and final assembly into longer peptide segments or specialized amide-rich structures.
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