Boc-N-Me-Thr-OH is a protected, N-methylated threonine derivative in which the amino terminus is masked as a Boc carbamate while the carboxyl group remains as a free acid, yielding a threonine-based amino acid building block for peptide chemistry. The molecule contains an N-methyl substituent on the amino nitrogen, a threonine side chain bearing a hydroxyl-bearing aliphatic functionality, and a stereocenter at the threonine α-carbon when present in the supplied structure, with the Boc group providing chemoselective control by reducing unprotected amine reactivity. Boc-N-Me-Thr-OH is used as a precursor for stepwise assembly of peptides and peptide analogues, where the protected amine and free carboxyl enable controlled coupling to neighboring residues and support structure-activity studies that probe the effect of N-methylation and side-chain hydroxyl presence on peptide properties.
CAT No: CP26134
CAS No:101759-72-2
Synonyms/Alias:Boc-N-methyl-L-threonine;101759-72-2;L-Threonine,N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-;BOC-N-ME-THR-OH;SCHEMBL1486174;CTK8B2905;ZINC2392274;ANW-41297;AKOS015908219;AJ-35823;AK-89024;SC-20598;RT-011785;X5878;B-6259;I14-24514;N-ALPHA-(T-BUTYLOXYCARBONYL)-N-ALPHA-METHYL-L-THREONINE;(2S,3R)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-hydroxybutanoicacid
Boc-N-Me-Thr-OH is a Boc-protected, N-methylated threonine derivative designed for controlled incorporation of an N-methyl amino acid unit into peptides and peptide-like scaffolds. The threonine side chain provides a hydroxyl functional group for downstream selective modification or retention, while the N-methyl substitution modulates amide hydrogen-bonding and conformational preferences relevant to peptide structure design. As a protected amino acid building block, it is commonly handled as a stable coupling component for peptide synthesis workflows and for preparing defined intermediates in medicinal chemistry programs.
1. Peptide Building Block
Boc-N-Me-Thr-OH is used as a defined amino acid building block for assembling peptides where an N-methyl threonine residue is required to tune backbone hydrogen-bonding capacity and local conformation. Peptide synthesis teams in academic and industrial medicinal chemistry frequently select this reagent to introduce N-methylated amide character at specific positions, enabling systematic structure-property studies in lead optimization campaigns and peptide library construction. The Boc protection supports standard peptide coupling workflows, while the threonine side-chain hydroxyl allows either retention for later functionalization or controlled protection strategies during subsequent synthetic steps.
2. Medicinal Chemistry Intermediates
Boc-N-Me-Thr-OH serves as a practical intermediate for preparing N-methylated threonine-containing fragments used in peptidomimetic and constrained peptide analog development. Medicinal chemistry groups developing structure-activity relationship (SAR) series often rely on such protected, stereochemically defined amino acid derivatives to generate consistent building blocks for fragment coupling, late-stage diversification, and analog synthesis. The combination of Boc protection and N-methylation provides a convenient handle for building defined amide motifs, while the threonine hydroxyl supports downstream derivatization routes that are commonly used to vary polarity, hydrogen-bonding patterns, and overall scaffold properties.
3. Protected Amino Acid Coupling
Boc-N-Me-Thr-OH is frequently selected by peptide manufacturing and synthesis specialists as a protected coupling component to ensure that both the amino functionality and the N-methylated amide environment are introduced in a controlled manner. In custom peptide synthesis workflows, this reagent helps maintain positional fidelity of the N-methylated residue within longer sequences, which is important when producing standards, analytical peptides, or reference compounds for method development. The threonine side-chain hydroxyl further supports the creation of well-defined intermediates, either for direct continuation of peptide assembly or for conversion into side-chain-modified derivatives as part of a planned synthetic sequence.
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