Adpoc-Trp-OH

Adpoc-Trp-OH is an N-(ADPoc) protected tryptophan derivative bearing a free carboxylic acid (Trp-OH) and the indole-containing side chain characteristic of tryptophan. The molecule contains an amino acid backbone with an N-protecting group (ADPoc) that masks the α-amino functionality while leaving the indole ring and the α-carboxyl group available for further chemical handling, and the stereochemical configuration is not specified in the name. In peptide synthesis workflows, the protected amino acid is employed as a building block for stepwise assembly of tryptophan-containing peptides, where the N-protection supports chemoselective coupling and the free carboxyl group enables formation of peptide bonds under standard amino-acid coupling conditions.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP27359

CAS No:68388-91-0

Synonyms/Alias:Adpoc-Trp-OH;68388-91-0

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M.F/Formula
C26H34N2O4
M.W/Mr.
424.55

Adpoc-Trp-OH is an amino acid building block derived from tryptophan, supplied as a protected carboxylic acid suitable for peptide and peptidomimetic assembly. The indole-containing side chain of tryptophan is preserved for incorporation into bioactive sequences, while the N-terminus is masked to enable controlled coupling chemistry during fragment condensation. This protected tryptophan derivative is commonly used by peptide synthesis groups that require reliable handling of the indole functionality and a defined amino acid unit for downstream purification and characterization.

1. Solid-Phase Peptide Synthesis

Adpoc-Trp-OH is used as a tryptophan-containing residue during solid-phase peptide synthesis workflows, particularly when a protected amino acid unit is needed for stepwise chain elongation. Peptide synthesis teams select this type of protected tryptophan building block to maintain chemoselectivity at the amino terminus while allowing the indole side chain to remain available for the intended sequence context. The resulting peptide segments are typically assembled as protected intermediates that can be carried forward into purification and final deprotection steps, supporting routine generation of Trp-containing peptides for structure-activity studies and biochemical assays.

2. Solution-Phase Fragment Coupling

Adpoc-Trp-OH serves as a defined tryptophan component for solution-phase peptide synthesis and segment condensation, where discrete amino acid fragments are assembled under controlled coupling conditions. Researchers developing longer peptides or complex sequences often rely on protected amino acid derivatives to improve reproducibility across coupling steps and to manage functional group compatibility during purification. In these workflows, Adpoc-Trp-OH provides a standardized Trp residue for constructing peptide fragments that can later be joined to form full-length targets, including peptides used for receptor binding studies, enzyme substrate mapping, and epitope generation.

3. Peptidomimetic and SAR Intermediates

Adpoc-Trp-OH is also used in medicinal chemistry programs that build peptidomimetic scaffolds and structure-activity relationship (SAR) libraries where tryptophan is incorporated as a key side-chain element. Synthetic chemists value protected amino acid building blocks for assembling analog series with consistent stereochemical identity and a stable, isolable intermediate form. By using Adpoc-Trp-OH as a tryptophan unit in the precursor stage, teams can generate a range of Trp-containing intermediates that feed into subsequent functionalization, conjugation, or final assembly steps toward lead optimization candidates and tool compounds.

Size
1 g;5 g;
InChI
1S/C26H34N2O4/c1-25(2,15-26-11-16-7-17(12-26)9-18(8-16)13-26)32-24(31)28-22(23(29)30)10-19-14-27-21-6-4-3-5-20(19)21/h3-6,14,16-18,22,27H,7-13,15H2,1-2H3,(H,28,31)(H,29,30)/t16?,17?,18?,22-,26?/m0/s1
InChI Key
WCCIXRYSJDUEOF-ZYTNRUGMSA-N
Canonical SMILES
CC(C)(CC12CC3CC(C1)CC(C3)C2)OC(=O)NC(CC4=CNC5=CC=CC=C54)C(=O)O

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