L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is a non-proteinogenic amino acid derivative featuring a tetrahydroisoquinoline ring system bearing a carboxylic acid at the 3-position and an amino acid-like side chain that places an amino functional group in the same molecule as the α-carboxyl group. The structure contains both amino and carboxyl functional groups and a saturated fused heterocycle, with stereochemistry consistent with the "L" designation in the product name and the ring substitution pattern implied by the tetrahydroisoquinoline framework. In research workflows, this compound is used as a building block for peptide and peptidomimetic synthesis and for structure-activity or chemical biology studies where a rigid, heterocyclic side chain and defined stereochemical context are needed for evaluating binding, conformation, or labeling strategies.
CAT No: CP23702
CAS No:74163-81-8
Synonyms/Alias:74163-81-8;(S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylicacid;L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylicacid;(S)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylicacid;(S)-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylicAcid;(3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylicacid;UNII-737G46U1NP;1,2,3,4-Tetrahydroisoquinoline-3(s)-carboxylicacid;S-(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylicacid;1,2,3,4-Tetrahydroisoquinoline-3(R)-carboxylicacid;L-Porretine;PubChem6296;AC1MBYEG;(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylicacid;AC1Q71AH;KSC489O6L;SCHEMBL288272;421626_ALDRICH;CHEMBL447576;87437_FLUKA;CTK3I9765;BWKMGYQJPOAASG-VIFPVBQESA-N;MolPort-001-758-753;737G46U1NP;ACT01929
L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is a chiral, amino-acid-like carboxylic acid bearing a tetrahydroisoquinoline scaffold fused with a stereodefined ring system. The molecule contains a ring nitrogen within the heterocycle and a carboxylic acid at the 3-position, enabling acid-base behavior and productive coupling chemistry under peptide-relevant conditions. The saturated aromatic-like framework provides conformational rigidity that can influence binding-site recognition in molecular design and SAR studies, while the chiral center(s) support stereoselective synthesis and downstream derivatization. The compound functions as a heterocyclic amino acid intermediate suitable for conversion into protected derivatives, activated esters, and amide-forming intermediates used in peptide analog construction and fine chemical synthesis.
1. Peptide Synthesis
L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid serves as a heterocyclic amino acid building block for peptide coupling workflows that require a carboxyl group and a stereodefined backbone. The carboxylic acid can be transformed into peptide-compatible activated species, while the ring nitrogen can be managed through N-protection strategies to prevent side reactions during coupling and subsequent deprotection steps. The conformationally constrained tetrahydroisoquinoline motif can be incorporated into short peptides and peptidomimetics to probe how rigid side-chain topology affects amide bond formation, conformational preferences, and receptor-like binding interactions. Downstream use commonly includes synthesis of analog libraries for structure-activity relationship studies and preparation of sequence-defined peptide fragments for biochemical assays.
2. Chiral Building Block Development
L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid functions as a chiral heterocycle-containing amino acid intermediate for stereoselective synthesis routes that require controlled configuration at the ring-bearing stereocenter(s). The presence of both a carboxylic acid and a basic ring nitrogen supports orthogonal protection designs, enabling selective activation at the acid while maintaining compatibility with subsequent functional-group manipulations. The rigid tetrahydroisoquinoline framework can be leveraged to generate enantiopure derivatives for chiral ligand studies, asymmetric synthesis investigations, and stereochemical mapping of peptide-like scaffolds. The resulting protected or activated forms can feed into downstream amide formation, salt formation, and analytical standard development for enantiomeric purity assessment.
3. Side-Chain Functionalization
L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid supports side-chain and heterocycle modification strategies that target the ring nitrogen and the carboxyl functionality while preserving the stereochemical integrity of the scaffold. The basic nitrogen can be converted into N-derivatives that modulate reactivity and solubility, enabling controlled transformations such as N-alkylation, N-acylation, or conversion into protected states compatible with peptide chemistry. The carboxylic acid can be esterified or activated to generate intermediates for C-terminal modification, including amide or ester analogs used in SAR panels and chemical biology probes. The heterocyclic structure can also enable late-stage diversification to generate functionalized amino acid derivatives for binding studies, conjugation handles, and synthetic intermediate preparation.
4. Bioconjugation Chemistry
L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid can be applied in bioconjugation and chemical biology workflows where amino-acid-derived linkers are needed to connect biomolecules to probes or materials. The carboxyl group enables formation of stable amide linkages to lysine-like targets or to activated biomolecule scaffolds, while N-protection and deprotection strategies can be used to tune chemoselectivity during conjugation chemistry. The tetrahydroisoquinoline motif may serve as a conformationally restricted spacer that can influence local presentation of the conjugated moiety in labeling experiments and affinity-based assays. Downstream utility includes preparation of peptide conjugates, linker-bearing analogs for biomolecule labeling, and intermediate generation for probe synthesis that relies on amino-acid coupling compatibility.
5. Pharmaceutical Intermediate Preparation
L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is suitable for pharmaceutical intermediate preparation where heterocyclic amino acid analogs are used to construct drug-like peptidomimetics and scaffold fragments. The acid functionality supports conversion into manufacturing-relevant activated derivatives, while the ring nitrogen can be protected to ensure predictable coupling behavior and to control impurity formation during synthesis. The stereodefined tetrahydroisoquinoline core can be carried through multistep routes to deliver amide-forming intermediates and C-terminal variants used in medicinal chemistry synthesis campaigns. Industrial relevance extends to fine chemical production planning, including route design for protected amino acid derivatives and downstream formation of sequence-defined fragments compatible with broader synthetic methodology.
6. Process Chemistry Intermediate
L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid can be employed as a process chemistry intermediate for industrial manufacturing of heterocyclic amino acid derivatives and peptide-like building blocks. The combination of a carboxylic acid and a heterocyclic ring nitrogen enables systematic control of reactivity through salt formation, esterification/activation, and orthogonal N-protection schemes that support scalable coupling and purification strategies. The conformational rigidity of the tetrahydroisoquinoline scaffold can improve reproducibility of downstream product profiles by limiting conformational variability in intermediate derivatives and final amide products. Broader utility includes preparation of standardized intermediates for peptide coupling chemistry, solid-phase or solution-phase synthesis inputs, and analytical reference materials used to monitor stereochemical integrity across synthetic steps.
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