Fmoc-L-tetrahydroisoquinoline-3-carboxylic acid, CAS No. 136030-33-6

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136030-33-6

Catalog No. EBD134404

CAS 136030-33-6

Name Fmoc-L-tetrahydroisoquinoline-3-carboxylic acid

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Basic Information

Synonyms: Fmoc-L-Tic-OH Fmoc-L-1,2,3,4-tetrahydroisoquinoline-3-carboxylicacid N-(9-fluorenylmethoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylicacid Fmoc-L-tetrahydroisoquinoline-3-carboxylicacid (s)-()-2-(9-fluorenylmethoxycarbonyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylicacid (s)-(+)-2-(9-fluorenylmethoxycarbonyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylicacid (s)-n-fmoc-1,2,3,4-tetrahydroisoquinoline-3-carboxylicacid rarechembkpt0084 n-fmoc-l-1,2,3,4-tetrahydroisoquinoline-3-carboxylicacid n-alpha-(9-fluorenylmethoxycarbonyl)-l-1,2,3,4-tetrahydroisoquinoline-3-carboxylicacid n-alpha-(9-fluorenylmethyloxycarbonyl)-l-1,2,3,4-tetrahydroisoquinoline-3-carboxylicacid n-1-fmoc-l-1,2,3,4-tetrahydro-isoquinoline-3-carboxylicacid fmoc-tic-oh Fmoc-L-Tetrahydroisoquinoline-3-COOH

Molecular Formula: C25H21NO4

Molecular Weight: 399.44

MDL Number: MFCD00144368

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

Product Description:

Fmoc-L-tetrahydroisoquinoline-3-carboxylic acid (Fmoc-Tic-OH, CAS 136030-33-6) is a protected unnatural amino acid derivative. Its structure features a tetrahydroisoquinoline (Tic) scaffold, a rigid, bicyclic heterocycle, with a carboxylic acid functional group. The amino group is protected by a fluorenylmethyloxycarbonyl (Fmoc) group, which is standard for solid-phase peptide synthesis (SPPS). This compound is primarily used as a specialized building block in peptide chemistry and medicinal chemistry research. The incorporation of the constrained Tic moiety into peptide sequences can significantly alter the peptide's conformation, enhance metabolic stability, and improve receptor binding affinity or selectivity. It is particularly valuable for designing peptidomimetics, enzyme inhibitors, and bioactive peptides targeting various receptors (e.g., opioid receptors). As an Fmoc-protected amino acid, it is directly compatible with standard Fmoc-SPPS protocols. Its main application lies in the synthesis of non-natural peptides and peptide-based drug candidates, where it serves as a key intermediate to introduce structural rigidity and specific pharmacophoric features.

Physical Properties

Melting Point: 146-149 °C

Boiling Point: 629.9 °C at 760 mmHg

Flash Point: 334.7 °C

Density: 1.324 g/cm3

Solubility: 1mmol in 2mL DMF

Storage: 2-8°C

Analytical Data

Appearance: white - off-white crystalline powder