N-α-Boc-N-in-formyl-L-1,2,3,4- tetrahydronorharmane -3-carboxylic acid is a protected amino acid derivative featuring a tetrahydronorharmane-derived ring system substituted at the 3-position with a carboxylic acid and bearing an N-in-formyl group on the amino nitrogen. The molecule contains a free carboxyl functional group while the α-amino functionality is masked by a Boc (tert-butoxycarbonyl) protecting group and further modified by an N-formyl (in-formyl) substituent, with stereochemistry indicated as L for the α-center as named. In peptide-synthesis and related synthetic chemistry contexts, the Boc and formyl protections provide chemoselective control over amide-forming steps and support stepwise assembly or derivatization of the amino acid building block for incorporation into more complex amino acid and peptide structures.
CAT No: CP23806
N-α-Boc-N-in-formyl-L-1,2,3,4-tetrahydronorharmane-3-carboxylic acid is an L-configured, amino acid-derived chiral intermediate featuring a tetrahydronorharmane ring system and a carboxylic acid at the 3-position. The molecule bears an N-α Boc protecting group and an N-in-formyl substituent, creating a protected amide/urethane-like nitrogen environment that modulates nucleophilicity and controls coupling behavior. The presence of a free carboxylic acid enables conversion to activated esters or peptide coupling partners, while the rigid bicyclic/heterocycle-like framework supports stereochemically defined downstream transformations. The formylated, Boc-protected nitrogen and the chiral center together make the compound suitable for stepwise deprotection and peptide-compatible derivatization in both synthetic methodology development and fine chemical manufacturing.
1. Protected Amino Acid Synthesis
N-α-Boc-N-in-formyl-L-1,2,3,4-tetrahydronorharmane-3-carboxylic acid serves as a protected amino acid building block for protected amino acid synthesis workflows that require orthogonal nitrogen protection. The Boc group on the α-amino functionality and the N-in-formyl substituent provide distinct deprotection and reactivity profiles, supporting controlled peptide coupling chemistry without premature side reactions. The carboxylic acid at the 3-position can be transformed into peptide coupling-ready derivatives, enabling incorporation into amide bonds under standard amino acid coupling conditions. The resulting protected chiral intermediate is suitable for sequential synthesis of longer peptide fragments and for preparing stereodefined amino acid derivatives used in medicinal chemistry and chemical biology.
2. Peptide Synthesis
N-α-Boc-N-in-formyl-L-1,2,3,4-tetrahydronorharmane-3-carboxylic acid functions in peptide synthesis as a chiral, N-protected amino acid analog that can be incorporated into peptide chains to introduce a rigid tetrahydronorharmane side-chain motif. The α-Boc protection supports temporary protection during chain assembly, while the formylated nitrogen can influence chemoselectivity during coupling and subsequent deprotection sequences. The free carboxylic acid provides the handle needed for conversion to activated intermediates that participate in amide bond formation at the C-terminus position of the growing peptide. Downstream, the protected residue can be used to generate peptidomimetics and structure-defined peptide analogs that probe how constrained ring systems affect folding, binding, and molecular recognition.
3. Peptidomimetics And SAR Studies
N-α-Boc-N-in-formyl-L-1,2,3,4-tetrahydronorharmane-3-carboxylic acid supports peptidomimetics and structure-activity relationship studies by enabling systematic variation of a chiral, ring-constrained amino acid unit within bioactive scaffolds. The tetrahydronorharmane framework provides a defined three-dimensional shape and hydrophobic/heterocycle-like character, while the protected nitrogen and carboxylic acid allow controlled installation into analog series. Stepwise deprotection and functional group interconversion can be applied to generate analogs with modified N-termini, C-terminal derivatives, or alternative amide linkages for SAR mapping. The compound thus serves as a practical chemical intermediate for building stereodefined libraries that connect amino acid derivatization to measurable structure-function outcomes.
4. Chemical Biology Conjugation
N-α-Boc-N-in-formyl-L-1,2,3,4-tetrahydronorharmane-3-carboxylic acid can be used in chemical biology conjugation strategies where amino acid-derived linkers are required to attach constrained motifs to biomolecular targets. The carboxylic acid enables formation of activated ester or coupling-ready derivatives that can be directed toward amide or ester linkages with nucleophilic partners on proteins, peptides, or affinity tags. The Boc and formyl protections help preserve the chiral nitrogen-bearing functionality during conjugation setup, allowing deprotection at a chosen stage to expose the reactive amine when needed. The resulting conjugates can be applied to biomolecule labeling, probe construction, and mechanistic studies where stereochemistry and rigid ring presentation affect recognition.
5. Pharmaceutical Intermediate Preparation
N-α-Boc-N-in-formyl-L-1,2,3,4-tetrahydronorharmane-3-carboxylic acid is suitable for pharmaceutical intermediate preparation in fine chemical synthesis routes that require protected chiral amino acid derivatives. The orthogonally protected nitrogen architecture (Boc plus N-in-formyl) supports manufacturing-oriented protection/deprotection planning, helping manage chemoselectivity during conversion to coupling partners and downstream functionalization. The carboxylic acid functionality supports controlled activation steps for incorporation into larger intermediates, including peptide-like fragments and constrained amide-containing motifs. The compound's stereochemical integrity and protected-group stability make it applicable as a process chemistry intermediate for generating defined chiral building blocks used in drug discovery chemistry and related applied synthesis programs.
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