L-4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid is a heterocyclic amino acid derivative featuring a fused imidazo[4,5-c]pyridine ring system with a carboxylic acid substituent at the 6-position, classifiable as a non-proteinogenic amino acid analogue. The molecule contains an amino-bearing heterocycle framework (with the "1H" imidazole nitrogen specified in the ring) and a free carboxyl group, and its partially saturated tetrahydro segment defines the ring's hydrogenation state while the "L-" designation indicates a specific stereochemical form when applicable to the named chiral center(s). In synthesis and chemical biology contexts, this scaffold-bearing amino acid is used as a defined building block for incorporating rigid heteroaromatic character into peptide-like structures, for structure-activity studies, and for analytical method development where heterocycle-containing amino acid analogues are required.
CAT No: CP27257
CAS No:59981-63-4
Synonyms/Alias:Spinacine (L-4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid);Spinacine
L-4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid is a chiral, bicyclic amino-acid-like heterocycle featuring a fused imidazo[4,5-c]pyridine core with a tetrahydro ring system and a carboxylic acid at the 6-position. The structure presents a stereogenic center within the saturated ring framework, while the carboxyl group provides a controllable handle for amide formation, salt formation, and peptide-coupling compatible activation. The ring nitrogen atoms contribute defined basicity and hydrogen-bonding patterns that can influence conformational preferences and binding-site recognition in medicinal chemistry contexts. As a heteroaromatic carboxylic acid, the compound can function as a chiral building block for protected amino acid synthesis, peptidomimetic construction, and downstream functional group elaboration into amide, ester, and N-substituted derivatives.
1. Peptide Synthesis
L-4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid supports peptide coupling chemistry through its carboxylic acid, which can be converted into activated esters or acylating intermediates compatible with standard peptide coupling strategies. The heterocyclic nitrogens allow access to N-protection and deprotection workflows that can be tuned to preserve ring integrity during chain assembly. Incorporation of this chiral heterocycle into peptide sequences can provide conformational constraint and altered hydrogen-bonding geometry relative to canonical amino acids. The resulting amide-linked products can serve as peptide building blocks for structure-activity relationship studies and for generating peptide analog libraries in applied peptide science.
2. Peptidomimetics And SAR Studies
L-4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid is suitable for peptidomimetic construction where a rigid bicyclic scaffold replaces or decorates an amino-acid residue to modulate binding interactions. The fused imidazo[4,5-c]pyridine architecture and defined stereochemistry can influence torsional angles and side-chain orientation when embedded into amide frameworks. The carboxyl functionality enables straightforward derivatization into amides, esters, or carboxylate salts that can be used to probe SAR trends across series. Downstream derivatives prepared from this building block can be applied to medicinal chemistry campaigns focused on mapping how heteroaromatic ring electronics and stereochemical configuration affect molecular recognition.
3. Chiral Building Block Chemistry
L-4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid functions as a chiral amino-acid-like intermediate for stereoselective synthesis of nitrogen-rich heterocycles. The stereogenic center within the tetrahydro ring and the presence of multiple ring nitrogens support rational protection-group selection to manage chemoselectivity during functionalization and coupling steps. Carboxyl activation and subsequent conversion into protected forms such as esters or acyl derivatives can enable sequential transformations while maintaining stereochemical integrity. The compound can be employed to prepare chiral intermediates for fine chemical synthesis, including downstream N-substituted analogs and amide-containing heterocyclic products used in research-grade molecular design.
4. Chemical Biology And Target Probing
L-4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid can be applied in chemical biology workflows that require heteroaromatic, amide-forming probes with defined hydrogen-bonding and basicity. The carboxylic acid enables conjugation-ready handles through conversion to activated esters and subsequent formation of stable amide linkages to biomolecule scaffolds or linker systems. The bicyclic imidazo[4,5-c]pyridine core can participate in specific intermolecular interactions, supporting its use in binding assays, competition studies, and mechanistic investigations where stereochemistry matters. Prepared conjugates and labeled analogs derived from this compound can serve as tools for interrogating receptor-ligand or protein-ligand recognition patterns in biochemical research.
5. Pharmaceutical Intermediate Preparation
L-4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid is relevant to pharmaceutical intermediate preparation due to its carboxylic acid functionality and heteroaromatic nitrogen content that align with common medicinal chemistry derivatization routes. The compound can be transformed into acyl derivatives, ester intermediates, or protected forms that support sequential synthesis toward drug-like heterocycle-containing scaffolds. The chiral tetrahydro-fused stereochemistry provides a defined spatial arrangement that can be carried through to later-stage structure elaboration. Industrially, this amino-acid-like heterocycle can serve as a process chemistry intermediate for manufacturing of amide-bearing heterocyclic building blocks used in fine chemical production and applied synthesis of complex molecules.
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