Boc-1,4-cis-ACHC-OH

Boc-1,4-cis-ACHC-OH is a Boc-protected, non-proteinogenic amino acid building block featuring the 1,4-cis-aminocyclohexane carboxylic acid (ACHC) framework, which provides conformationally restricted geometry for peptide and peptidomimetic design. The presence of the N-Boc protecting group makes it a practical intermediate for controlled incorporation into amide linkages during peptide synthesis workflows. Researchers use this stereodefined scaffold to access rigid backbone elements that support structure-activity relationship studies and the development of constrained peptide analogs.

1. Constrained Peptide Synthesis

Boc-1,4-cis-ACHC-OH is used by peptide chemistry groups to introduce a conformationally restricted ACHC residue into peptide sequences where backbone rigidity is desired. The N-Boc protection supports stepwise assembly into protected peptide intermediates, enabling downstream coupling strategies that require a stable amino component while maintaining the stereochemical integrity of the cis-1,4 arrangement. This building block is particularly valued in custom peptide synthesis for generating analog series used in SAR campaigns, where the constrained geometry of the ACHC side-chain framework can be used to probe how local conformations influence properties such as receptor/ligand recognition or functional presentation in assays.

2. Peptidomimetic SAR Development

Boc-1,4-cis-ACHC-OH serves as a specialized amino acid derivative for medicinal chemistry teams developing peptidomimetics and constrained analogs. The rigid aminocyclohexane motif helps translate structural hypotheses into synthetic constructs by replacing more flexible residues with a defined cis-1,4 scaffold. In practice, this supports the preparation of focused libraries of analogs used for structure-activity relationship studies, allowing chemists to evaluate how conformational control impacts measurable readouts in biochemical or cell-free screening formats without changing the overall peptide length. The Boc-protected form streamlines its use as a defined intermediate when building amide-linked analogs for iterative design cycles.

3. Pharmaceutical Intermediate Manufacturing

Boc-1,4-cis-ACHC-OH is also relevant as a stereodefined pharmaceutical intermediate for manufacturing workflows that require incorporation of the ACHC motif into larger protected fragments or final peptide-like intermediates. Process development and specialty synthesis teams rely on such protected, configuration-controlled amino acid building blocks to reduce variability during downstream assembly steps and to ensure consistent stereochemical outcomes across batches. This makes the material a practical choice when producing defined constrained-residue segments for later coupling, purification, and final assembly into advanced intermediates used in preclinical chemistry programs and specialty chemical production.

4. Stereodefined Building Block

Boc-1,4-cis-ACHC-OH is frequently selected by structural chemistry and chemical biology researchers who need a stereochemically defined aminocyclohexane residue to construct rigid analogs for conformational studies. The cis-1,4 geometry provides a useful handle for generating peptides or peptidomimetics with reduced conformational freedom, supporting experiments that compare constrained versus flexible analogs under consistent synthesis conditions. In these workflows, the Boc-protected amino functionality is used as a controlled synthetic entry point for building amide connectivity while preserving the stereodefined scaffold that underpins the experimental design.

1. An Isolated TCR αβ Restricted by HLA-A* 02: 01/CT37 Peptide Redirecting CD8+ T Cells to Kill and Secrete IFN-γ in Response to Lung Adenocarcinoma Cell Lines

2. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

3. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists

4. Myotropic activity of allatostatins in tenebrionid beetles

5. Multifunctional peptide-oligonucleotide conjugate promoted sensitive electrochemical biosensing of cardiac troponin I