(Boc)2-4-trans-Gmc-OH is a protected amino acid derivative featuring a glutamic acid-like backbone bearing a 4-trans substituent and two N-protecting Boc groups, placing it in the class of Boc-protected amino acid analogues used for peptide chemistry. The molecule contains a free carboxylic acid functional group alongside Boc-protected amino functionality, and the "trans" descriptor specifies the relative stereochemical relationship of the 4-substituted center as indicated by the product name. In synthesis, the Boc protection pattern supports controlled chemoselectivity during stepwise coupling in peptide assembly and enables preparation of more complex amino acid and peptide derivatives from a structurally defined, stereochemically specified intermediate.
CAT No: CP25274
CAS No:1263047-40-0
Synonyms/Alias:4-trans-(Boc2-guanidino)methycyclohexane carboxylic acid
Chemical Name:4-trans-[Bis(t-butyloxycarbonyl)-guanidino]methylcyclohexane carboxylic acid
(Boc)2-4-trans-Gmc-OH is a Boc-protected amino acid derivative featuring a 4-trans substituted "Gmc" side-chain motif, supplied as a protected building block for downstream peptide and peptidomimetic assembly. The presence of two Boc-type protecting groups on the amino functionality makes the compound primarily a synthetic intermediate, enabling controlled coupling chemistry while minimizing side reactions during fragment preparation and purification. In practice, researchers select this protected form when they need a defined stereochemical side-chain architecture and orthogonal handling through protected-group strategies.
1. Peptidomimetic Building Blocks
(Boc)2-4-trans-Gmc-OH is used by medicinal chemistry and peptide-optimization groups to construct peptidomimetic scaffolds where the 4-trans side-chain geometry must be retained through synthesis. The dual Boc protection supports predictable fragment handling in multi-step sequence assembly workflows, including the preparation of defined amino acid segments for custom peptide synthesis. This intermediate is commonly chosen when the target structure requires a specific stereochemical substitution pattern that would be difficult to control using unprotected or less-defined precursors.
2. Protected Amino Acid Segment Synthesis
(Boc)2-4-trans-Gmc-OH serves as a protected amino acid segment for solution-phase and custom fragment condensation strategies, where the protected amine functionality is required to manage chemoselectivity across coupling and purification steps. Peptide synthesis teams use derivatives like this to standardize building-block quality for assembling longer sequences, particularly when the side-chain substitution pattern ("4-trans" Gmc motif) is a structural determinant of the final peptide or peptidomimetic. By keeping the amine protected during segment preparation, the intermediate supports streamlined downstream conversion into the corresponding coupling-ready amino acid form used in sequence assembly.
3. Pharmaceutical Intermediate Development
(Boc)2-4-trans-Gmc-OH is applied in the development of defined, stereochemically specified intermediates for research-scale manufacturing of peptide-based candidates and related analogs. Process chemists and intermediate-development teams value protected amino acid derivatives because they provide a stable, isolable form that can be carried through controlled synthetic steps before incorporation into the target sequence. The Boc-protected functionality and fixed 4-trans side-chain architecture make this compound a practical choice when building-block reproducibility and structural fidelity are required for iterative SAR (structure-activity relationship) or analog library synthesis.
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