Boc-alpha-Me-D-Pro-OH is a protected, non-natural amino acid derivative based on the D-proline scaffold bearing an alpha-methyl substituent, with the nitrogen protected as a Boc (tert-butoxycarbonyl) carbamate. The molecule contains the free carboxylic acid functional group and a secondary amine masked by the Boc group, while the cyclic proline ring presents a constrained side chain and the alpha-methyl substitution modulates steric and conformational properties relative to unsubstituted proline derivatives. In peptide chemistry, this Boc-protected amino acid is employed as a building block for stepwise peptide synthesis and for preparing proline-containing analogues where alpha-methyl substitution and D-configuration are used to probe structure-property relationships, conformational effects, or labeling strategies in chemical biology research.
CAT No: CP25433
CAS No:166170-15-6
Synonyms/Alias:166170-15-6;(R)-1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylicacid;(R)-N-BOC-2-METHYLPROLINE;1-(TERT-BUTOXYCARBONYL)-2-METHYL-D-PROLINE;(2R)-1-(TERT-BUTOXYCARBONYL)-2-METHYL-2-PYRROLIDINECARBOXYLICACID;1-Boc-2-methyl-D-proline;N-Boc-|A-methyl-D-proline;SCHEMBL631031;BOC-ALPHA-ME-D-PRO-OH;CTK4D2263;MolPort-016-631-565;YQXRKJHVAUKXRN-LLVKDONJSA-N;ZINC391235;8446AA;AKOS005264633;AKOS015999951;CB-3440;PB13044;AJ-21074;AK122786;HE074763;AB0089251;KB-209572;ST24035174;Q-2078
Chemical Name:N-alpha-t-Butyloxycarbonyl-alpha-Methyl-D-proline
Boc-alpha-Me-D-Pro-OH is a Boc-protected, stereochemically defined proline derivative featuring an alpha-methyl substitution and D-configuration at the ring nitrogen-bearing stereocenter. As a protected amino acid building block, it is designed for incorporation into peptide and peptidomimetic sequences where conformational bias and steric modulation from the alpha-methyl group are used to influence backbone geometry and structure. The Boc group provides an N-protection strategy commonly used in peptide assembly workflows, while the amino acid's carboxylic acid functionality supports downstream coupling chemistry for fragment condensation.
1. Peptide Synthesis Building Block
Boc-alpha-Me-D-Pro-OH is used by peptide chemists to construct peptides and peptidomimetics that require a D-Proline residue with an alpha-methyl substituent. The Boc-protection supports routine peptide assembly strategies, enabling controlled N-terminus formation during stepwise chain growth. Researchers commonly select this residue when they want to introduce conformational restriction and steric effects at the alpha-position, which can be valuable in designing cyclic or constrained segments, improving synthetic access to non-native stereochemical patterns, and supporting structure-activity relationship studies in medicinal chemistry programs.
2. Peptidomimetic Medicinal Chemistry
Boc-alpha-Me-D-Pro-OH serves as a specialized intermediate for medicinal chemistry teams developing peptidomimetics and constrained analogs of bioactive peptide scaffolds. The combination of D-configuration and alpha-methyl substitution helps chemists probe how stereochemistry and backbone sterics affect folding preferences, local geometry, and overall scaffold presentation in SAR campaigns. This building block is typically integrated into solution-phase or solid-phase workflows to generate defined analog series, where the residue's stereochemical identity and N-protection are important for reproducible structure definition across parallel syntheses.
3. Stereodefined Fragment Coupling
Boc-alpha-Me-D-Pro-OH is frequently employed in fragment condensation and segment assembly when stereochemical fidelity and protected functionality are required for reliable downstream coupling. The presence of a Boc-protected nitrogen and a free carboxylic acid allows chemists to couple this residue into larger peptide fragments while maintaining the intended stereochemical arrangement at the proline center. In custom peptide manufacturing and research synthesis, this helps reduce variability when preparing multi-residue constructs that include D-amino acid motifs and alpha-substituted proline analogs for conformational studies and analytical reference material generation.
4. Non-Native Backbone Engineering
Boc-alpha-Me-D-Pro-OH is used in protein and peptide engineering research to introduce non-native backbone features into synthetic peptides that model or probe structural hypotheses. By installing an alpha-methylated D-proline unit, researchers can test how altered backbone sterics and stereochemical inversion impact secondary-structure propensity and local conformational constraints in designed sequences. This building block is particularly valuable when the goal is to generate well-defined, stereochemically controlled peptide analogs for biophysical characterization, structure-property mapping, or as defined inputs to chemical biology workflows that rely on synthetic precision.
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