Boc-Leu-Pro-OH is a protected amino acid derivative that contains the dipeptide-like sequence leucine-proline with the N-terminus masked by a Boc (tert-butoxycarbonyl) protecting group and the C-terminus present as a carboxylic acid. The molecule features an aliphatic isobutyl side chain from leucine and a cyclic secondary amine within the proline residue, with the Boc carbamate controlling chemoselectivity by reducing the nucleophilicity of the terminal amino functionality. Boc-Leu-Pro-OH is used as a stepwise peptide synthesis intermediate in solution-phase or solid-phase strategies, where the protected N-terminus supports controlled coupling to extend peptide chains while the terminal carboxyl group serves as the acylation handle.
CAT No: CP27318
CAS No:64205-66-9
Synonyms/Alias:Z-D-Tyr-OH;Z-D-tyrosine;64205-12-5;N-Carbobenzoxy-D-tyrosine;N-Cbz-D-tyrosine;N-ALPHA-CBZ-D-TYROSINE;CHEMBL305478;n-[(benzyloxy)carbonyl]-d-tyrosine;(R)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoicacid;(R)-2-Benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionicacid;Cbz-D-Tyr;AC1LEHHX;CBZ-D-TYROSINE;UPCMLD00WV-86;97285_ALDRICH;AC1Q5R23;SCHEMBL6118298;97285_FLUKA;MolPort-003-939-990;UPCMLD00WV-86:002;BB_NC-1968;ZINC155939;AR-1K3243;BDBM50043797;KM0825
Boc-Leu-Pro-OH is a protected dipeptide building block featuring an N-terminal Boc (tert-butoxycarbonyl) group, a leucine residue, and a proline residue in the C-terminal carboxylic acid form. This structure provides a stable, pre-assembled peptide segment with the proline ring imposing conformational constraints, making it useful for controlled peptide chain extension in both research-grade peptide synthesis and pharmaceutical intermediate development. The Boc protection supports standard peptide assembly workflows where selective deprotection and coupling steps are used to build longer sequences.
1. Solid-Phase Peptide Assembly
Boc-Leu-Pro-OH is used as a pre-formed dipeptide segment for stepwise peptide construction, particularly when a leucine-proline motif is required with minimal variability in the coupling stage. Peptide synthesis groups in academic peptide chemistry labs and contract peptide manufacturing commonly incorporate this type of protected dipeptide building block into solid-phase peptide synthesis workflows to streamline fragment assembly and improve reproducibility across peptide libraries. The N-terminal Boc protection and the C-terminal carboxylic acid functionality align with downstream coupling strategies used for chain elongation, while the proline residue helps introduce conformational bias that is frequently leveraged in peptide design.
2. Peptide Fragment Coupling
Boc-Leu-Pro-OH serves as a practical intermediate for solution-phase or fragment-based peptide synthesis where researchers need a defined Leu-Pro unit to be introduced into a larger peptide framework. Medicinal chemistry and chemical biology teams often rely on such protected dipeptides to rapidly generate analog series by swapping neighboring residues while keeping the Leu-Pro segment constant, supporting structure-activity relationship studies that depend on precise sequence control. The presence of the Boc-protected N-terminus helps manage chemoselectivity during assembly, and the proline ring provides a rigid scaffold that can be maintained consistently from intermediate to final peptide product.
3. Pharmaceutical Intermediate Development
Boc-Leu-Pro-OH is also used in the development and preparation of peptide-based pharmaceutical intermediates, where controlled peptide fragment handling is important for downstream scale-up and manufacturing workflows. Process development chemists and peptide API intermediate teams may use this building block to construct protected peptide intermediates that later undergo further transformations to reach the desired protected or partially deprotected peptide state. The defined stereochemical residues and the stable Boc-protected N-terminus make it a convenient, sequence-specific input for constructing longer, more complex peptide intermediates used in custom peptide manufacturing and industrial peptide synthesis programs.
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