1,2,3,4-TETRAHYDROISOQUINOLINE-(3R)-CARBOXYLIC ACID;1,2,3,4-D-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;3-ISOQUINOLINECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-, (3R)-;(3R)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;H-D-TIC-OH;D-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;D-[3R]-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;D-TIC
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D-Tic-OH, chemically known as (2S)-2-aminobicyclo[3.1.0]hexan-6-ol or D-trans-4-hydroxyproline analog, is a specialized chiral building block widely utilized in modern medicinal chemistry and peptide synthesis. Its molecular formula is C₆H₁₁NO₂, and it typically carries the CAS number 139753-84-5, though specific stereochemical variants may have distinct identifiers depending on the exact synthetic route and purity grade. This compound features a rigid bicyclic framework that imposes significant conformational constraints on attached amino acid chains, making it an invaluable tool for stabilizing secondary structures such as beta-turns and helices within peptidomimetics.
In pharmaceutical research, D-Tic-OH serves as a critical scaffold for designing novel therapeutics targeting neurological disorders, cardiovascular diseases, and infectious agents. The hydroxyl group at the C6 position offers versatile functionalization opportunities, allowing chemists to conjugate various moieties for enhanced bioavailability or target specificity. Unlike flexible linear peptides, derivatives incorporating this bicyclic core often exhibit improved metabolic stability against proteolytic degradation, extending their half-life in biological systems. Furthermore, its unique stereochemistry enables the creation of highly selective receptor ligands with reduced off-target effects.
The compound is primarily employed by academic institutions and biotech firms during the early stages of drug discovery to screen potential lead compounds. It facilitates the optimization of peptide drugs by enhancing binding affinity and selectivity without compromising pharmacokinetic profiles. While not a bulk commodity chemical, high-purity D-Tic-OH is essential for synthesizing complex macrocycles and constrained oligomers used in advanced therapeutic modalities. Researchers value its ability to mimic natural amino acids while providing structural rigidity that mimics transition states in enzymatic reactions. As the demand for precision medicine grows, the role of such chiral bicyclic amines continues to expand, supporting the development of next-generation small molecule drugs and bioactive peptides with superior efficacy and safety profiles.