Boc-Ala-Pro-OH is a Boc-protected dipeptide acid composed of alanine and proline linked through an amide bond, where the N-terminus is protected by a tert-butoxycarbonyl (Boc) group and the C-terminus is present as a free carboxylic acid. The molecule therefore contains both an unprotected carboxyl group for further coupling and a Boc carbamate that masks the terminal amine, while the proline residue bears a cyclic secondary amide-forming side chain that constrains backbone conformation during peptide assembly. As a peptide-related intermediate, it is used in stepwise peptide synthesis and related derivatization workflows to introduce the Ala-Pro segment with controlled chemoselectivity at the protected N-terminus.
CAT No: CP27012
CAS No:33300-72-0
Synonyms/Alias:BOC-ALA-PRO-OH;33300-72-0;PubChem12333;t-butoxycarbonylalanylproline;SCHEMBL6242739;MolPort-020-004-576;QGJDXUIYIUGQGO-IUCAKERBSA-N;t-butoxycarbonyl-L-alanyl-L-proline;ZINC4899574;6263AH;N-t-butyloxycarbonyl-L-alanyl-L-proline;(2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]pyrrolidine-2-carboxylicAcid;N-tert.-butoxycarbonyl-L-alanyl-L-proline;K-7685;1-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-L-proline
Boc-Ala-Pro-OH is a Boc-protected dipeptide acid featuring alanine and proline residues in a protected, peptide-ready form. The N-terminus is protected as a Boc carbamate, while the C-terminus is present as a carboxylic acid suitable for further peptide chain extension or coupling. This type of building block is routinely used in peptide synthesis workflows to assemble short segments with defined stereochemistry and residue order, supporting reproducible preparation of protected peptide intermediates for downstream purification and characterization.
1. Peptide Segment Coupling
Boc-Ala-Pro-OH is used as a dipeptide building block in both solution-phase and solid-phase peptide synthesis to generate defined Ala-Pro segments during stepwise chain assembly. Peptide synthesis groups value the pre-organized residue sequence because it reduces variability associated with sequential coupling of individual amino acids, particularly when building larger fragments that require consistent intermediate handling. The Boc-protected N-terminus supports controlled deprotection and subsequent coupling steps in standard peptide workflows, while the C-terminal carboxylic acid enables straightforward activation and condensation onto the next amino acid residue or peptide segment.
2. Protected Intermediate For Synthesis
Boc-Ala-Pro-OH serves as a stable, isolable protected intermediate for pharmaceutical intermediate development and custom peptide manufacturing research where short, well-defined fragments are required for iterative assembly. Process development teams often select dipeptide acids like this to streamline fragment condensation strategies, improve intermediate traceability, and support efficient purification at the intermediate stage before advancing to longer sequences. The presence of the Boc group and the terminal carboxylic acid provides a practical "handle" for downstream transformation while maintaining the dipeptide motif intact for accurate sequence construction.
3. Ala-Pro Motif Incorporation
Boc-Ala-Pro-OH is commonly employed when the Ala-Pro motif is part of a target peptide sequence for structure-activity relationship studies, peptide library synthesis, or peptide-based reagent development. Researchers use this building block to introduce proline-containing local conformational features within a peptide chain while maintaining the alanine residue at the adjacent position, enabling controlled evaluation of sequence effects. By supplying a residue-ordered, protected dipeptide acid, it supports reproducible synthesis of analogs and minimizes sequence errors during fragment assembly and purification-focused peptide development workflows.
4. Analytical Reference Standards Support
Boc-Ala-Pro-OH is also used in analytical method development and characterization workflows as a defined peptide fragment standard for monitoring coupling efficiency, intermediate identity, and purification performance. Analytical chemists and peptide characterization teams can leverage the known composition and protected termini to validate LC-MS or HPLC retention behavior of related intermediates during process optimization. In peptide synthesis development, having a discrete, sequence-specific reference fragment helps confirm that expected dipeptide incorporation steps are proceeding correctly before scaling to longer assemblies.
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More