Boc-L-allo-Thr-OH*DCHA

Boc-L-allo-Thr-OH*DCHA is a Boc-protected, stereochemically specified amino acid derivative of threonine in the allo configuration, supplied as a salt with dicyclohexylamine (DCHA). The molecule bears a tert-butoxycarbonyl (Boc) protecting group on the α-amino functionality and retains a free carboxylic acid (-COOH), while the side chain contains a β-hydroxyl group characteristic of threonine analogues and the allo stereochemistry is reflected in the substituted chiral center arrangement. In peptide and amino acid derivative synthesis, the Boc protection supports chemoselective handling of the amino group while the free carboxyl group serves as the acylation handle for constructing peptide bonds, and the DCHA salt form can be used to manage solid-state properties and facilitate downstream coupling and purification workflows.

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

CAT No: CP25641

CAS No:23082-30-6

Synonyms/Alias:N-Boc-L-Allothreonine;23082-30-6;(2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxybutanoicacid;(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxybutanoicacid;AmbotzBAA1339;N-Boc-L-allo-threonine;SCHEMBL999110;CTK8B8573;LLHOYOCAAURYRL-WDSKDSINSA-N;MolPort-008-267-418;ZINC1576239;ANW-60732;AKOS016003345;AJ-27306;AK-81099;N-(tert-Butyloxycarbonyl)-L-allothreonine;N2-(tert-butoxycarbonyl)-L-allothreonine;KB-258646;TC-149477

Chemical Name:N-alpha-t-Butyloxycarbonyl-allo-L-threonine dicyclohexylamine

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M.F/Formula
C9H17NO5
M.W/Mr.
219,23*181,32 g/mole

Boc-L-allo-Thr-OH*DCHA is a Boc-protected L-allo threonine derivative supplied as a dicyclohexylammonium (DCHA) salt, combining a threonine side chain with a protected amino group for controlled peptide coupling. The stereochemical allo configuration and the presence of the DCHA counterion are particularly relevant for consistent reagent handling, weighing, and downstream peptide assembly. This protected amino acid building block is commonly used in peptide synthesis workflows where orthogonal protection and reliable coupling performance are required.

1. Solid-Phase Peptide Synthesis

Boc-L-allo-Thr-OH*DCHA is used as a protected amino acid building block for stepwise peptide assembly on solid supports, where the Boc group enables amino-functional protection during chain elongation. Peptide synthesis teams typically select this allo-threonine derivative when they need threonine incorporation with defined stereochemistry, such as in peptide libraries, structure-activity relationship studies, or sequence-specific analogs. The DCHA salt form supports practical reagent handling for automated or semi-automated workflows, helping laboratories maintain consistent coupling inputs across batches of protected amino acids.

2. Peptide Library Building Blocks

Boc-L-allo-Thr-OH*DCHA is a practical choice for constructing peptide libraries and analog panels in medicinal chemistry and chemical biology, especially when defined allo stereochemistry at the threonine position is a variable under study. Researchers rely on Boc-protected amino acids to standardize the protected building-block format across multiple residues, simplifying procurement and minimizing variability between different amino acid derivatives. This reagent format supports rapid generation of peptide variants where the threonine side-chain functionality is preserved for downstream peptide characterization, structure studies, or further chemical modification steps after peptide assembly.

3. Pharmaceutical Intermediate Development

Boc-L-allo-Thr-OH*DCHA is also used as a protected amino acid intermediate in the preparation of threonine-containing fragments and peptide-like intermediates for downstream medicinal chemistry programs. Process and development chemists commonly value Boc-protected amino acids as stable, isolable building blocks that integrate cleanly into protected intermediate sequences, enabling controlled progression toward larger targets. The allo configuration and protected amino functionality help ensure that the stereochemical and functional features required in the later-stage synthesis are carried through from the intermediate stage into the assembled product.

4. Stereodefined Amino Acid Analog Synthesis

Boc-L-allo-Thr-OH*DCHA supports the synthesis of stereodefined amino acid analogs where the allo arrangement at the threonine center is required to probe conformational effects or to generate sequence-accurate reference materials. In research settings such as peptide characterization and analytical standard preparation, laboratories often need protected, stereochemically defined amino acid inputs to produce consistent reference peptides and fragments for method development and comparison. The Boc-protected format allows these analogs to be incorporated into defined synthetic sequences while maintaining the threonine side-chain functionality for subsequent analytical or derivatization workflows.

Size
1 g;5 g;
InChI
1S/C9H17NO5/c1-5(11)6(7(12)13)10-8(14)15-9(2,3)4/h5-6,11H,1-4H3,(H,10,14)(H,12,13)/t5-,6-/m0/s1
InChI Key
LLHOYOCAAURYRL-WDSKDSINSA-N
Canonical SMILES
CC(C(C(=O)O)NC(=O)OC(C)(C)C)O

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