N-α-Boc-N-in-formyl-D-1,2,3,4- tetrahydronorharmane -3-carboxylic acid is a protected, non-proteinogenic amino acid derivative featuring a tetrahydronorharmane ring system bearing a carboxylic acid at the 3-position and an amino functionality masked as an N-formylated, Boc-protected amide/urethane-type protected group. The molecule contains a free carboxyl group and a stereochemically specified D-configuration at the amino acid center, while the N-α Boc group and the N-in-formyl substituent modulate chemoselectivity by suppressing unprotected amine reactivity during synthesis and downstream coupling. In peptide-chemistry and chemical biology workflows, this protected analogue is used as a building block for stepwise assembly of modified peptides or for preparing labeled and structurally constrained amino acid derivatives where the rigid tetrahydronorharmane scaffold and controlled N-protection are required for selective functional-group handling.
CAT No: CP23805
N-α-Boc-N-in-formyl-D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid is a chiral, amino-acid-like intermediate featuring a D-configured stereocenter at the 3-carboxylic acid position and a tetrahydronorharmane-derived bicyclic side structure that presents a rigid, nitrogen-containing scaffold. The molecule contains a carboxylic acid functional group for C-terminal peptide coupling and an N-substituted amide/urethane motif combining an N-formyl group with an N-α-Boc protecting group, which modulates nucleophilicity and controls chemoselectivity during synthesis. The N-in-formyl arrangement can participate in acyl-transfer chemistry after activation, while the Boc group supports standard orthogonal deprotection strategies to reveal the protected amine for peptide bond formation. The overall polarity and protected amine/acid pattern make it suitable as a chiral building block for peptide construction, peptidomimetic scaffolding, and downstream functionalization of the heterocyclic side chain.
1. Protected Amino Acid Synthesis
N-α-Boc-N-in-formyl-D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid is applied in protected amino acid synthesis workflows where orthogonal protection is required for controlled peptide coupling. The presence of a carboxylic acid enables activation to form peptide-ready acyl intermediates, while the N-α-Boc group and N-in-formyl moiety suppress undesired side reactions by reducing free amine reactivity. The D stereochemistry at the α-position provides a defined chiral center that can be retained through coupling steps, supporting stereochemically consistent protected amino acid building block preparation. The protected nitrogen pattern also supports sequential deprotection logic, enabling downstream conversion into a peptide-forming amine under conditions compatible with other protected residues.
2. Peptide Synthesis
N-α-Boc-N-in-formyl-D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid functions as a peptide building block for incorporating a tetrahydronorharmane-derived, nitrogen-containing side chain into peptide backbones. The carboxylic acid group supports standard peptide coupling chemistry to generate amide linkages, while the N-α-Boc protection helps maintain the residue as a stable, non-nucleophilic amine during assembly. The N-in-formyl feature can be leveraged for chemoselective transformations after coupling, including controlled unmasking strategies that expose the appropriate nucleophile for further elongation or derivatization. The rigid bicyclic scaffold can influence conformational preferences in the resulting peptide, making the building block relevant for constructing structured peptide analogs and stereodefined sequences.
3. Peptidomimetics And SAR Studies
N-α-Boc-N-in-formyl-D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid is used in peptidomimetic construction and structure-activity relationship studies where incorporation of a constrained heterocycle is needed to probe molecular recognition. The tetrahydronorharmane-derived side structure, together with the protected amine and carboxylic acid handles, supports systematic derivatization of peptide-like scaffolds while maintaining a defined stereochemical configuration. N-α-Boc and N-in-formyl protection strategies enable iterative synthesis of analog libraries by allowing selective deprotection and re-coupling without scrambling stereochemistry at the α-carbon. The resulting analogs can be employed as SAR probes to evaluate how side-chain rigidity and ring nitrogen placement affect binding modes and physicochemical properties relevant to amino acid derivative design.
4. Chemical Biology And Bioconjugation
N-α-Boc-N-in-formyl-D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid is suitable for chemical biology workflows that require amino acid-derived handles for controlled biomolecule modification. The protected carboxylic acid and masked amine enable synthesis of conjugatable peptide fragments or linkers that can later be attached to biomolecular targets through amide-forming or acyl-transfer-compatible steps. The heterocyclic nitrogen-containing scaffold can serve as a recognition element within labeled peptides or as a structural motif in affinity reagents, supporting downstream conjugation design. Orthogonal deprotection of the Boc-protected amine can be used to time the exposure of reactive functionality for coupling to amines, hydrazides, or other nucleophiles present in biomolecule labeling strategies, aligning with peptide science intermediate preparation.
5. Process Chemistry Intermediate
N-α-Boc-N-in-formyl-D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid is applied as a chiral intermediate in process chemistry intermediate preparation for fine chemical and pharmaceutical manufacturing supply chains. The combination of a single protected amine (Boc) and an N-in-formyl group provides a predictable chemoselectivity profile during activation of the carboxylic acid for peptide coupling or intermediate derivatization. The D-configured stereocenter supports stereochemically consistent downstream synthesis, which is critical for producing stereodefined peptide building blocks at scale. The protected functional group set can be integrated into manufacturing routes that include selective deprotection steps and controlled formation of amide bonds, enabling reliable conversion into peptide fragments, peptidomimetic precursors, and other amino acid derivative intermediates.
6. Analytical Research Standards
N-α-Boc-N-in-formyl-D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid is used in analytical research to prepare stereochemically defined standards for monitoring peptide synthesis and amino acid derivative transformations. The defined D stereochemistry and stable protected-group pattern support unambiguous chromatographic and mass spectrometric characterization of intermediates during protected amino acid chemistry, including verification of coupling outcomes and detection of deprotection-related species. The carboxylic acid and protected nitrogen functionalities allow formation of reference derivatives that can be used to validate analytical methods for complex peptide-like mixtures. The compound's role as a structurally specific chiral intermediate supports quality control of peptide building block preparation and downstream synthetic intermediate formation in applied amino acid and peptide science.
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