Boc-3,4-dehydroPro-OH is a Boc-protected dehydroproline derivative bearing a cyclic pyrrolidine ring with an unsaturation between the 3 and 4 positions, classifying it as a non-proteinogenic, conformationally constrained amino acid precursor for peptide chemistry. The molecule contains a free carboxylic acid (-COOH) and a Boc-protected amino functionality (N-Boc), with the side chain incorporated into the ring and the 3,4-dehydro motif providing an alkene that can influence backbone geometry during amide bond formation. In synthesis, this protected amino acid is used as a building block for stepwise peptide assembly, including solid-phase or solution-phase strategies, where the Boc group controls chemoselectivity of coupling while the dehydroalkene enables incorporation of unsaturated residues for structure-activity studies and chemical biology probes.
CAT No: CP25868
CAS No:51154-06-4
Synonyms/Alias:51154-06-4;(S)-1-(tert-Butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylicacid;Boc-3,4-Dehydro-L-proline;Boc-Delta3Pro;AmbotzBAA1460;AC1LELZE;Boc-Delta(3)Pro-OH;B2511_SIGMA;SCHEMBL629585;N-Boc-3,4-Dehydro-Pro-OH;CTK7I3195;ZINC57212;BOC-3,4-DEHYDRO-PRO-OH;BMIGSRMSSCUMAZ-ZETCQYMHSA-N;MolPort-003-725-575;AKOS015907944;EBD2208185;AJ-09630;AK115638;SC-72404;TR-018236;ST24026491;Z5903;K-9425;1-(tert-Butoxycarbonyl)-3,4-didehydro-L-proline
Chemical Name:N-alpha-t-Butyloxycarbonyl-3,4-dehydro-L-proline
Boc-3,4-dehydroPro-OH is a Boc-protected dehydroproline amino acid building block bearing a constrained 3,4-unsaturated ring motif, supplied as a carboxylic acid for downstream peptide coupling. The N-terminal Boc group enables controlled incorporation into protected peptide segments, while the dehydro (alkene) functionality supports the preparation of conformationally restricted peptides and peptidomimetic scaffolds used in structure-function studies. Researchers select this reagent when they need a proline analog with an unsaturation handle to probe backbone geometry and improve chemical diversity in peptide synthesis workflows.
1. Constrained Peptide Building
Boc-3,4-dehydroPro-OH is used by custom peptide synthesis groups and medicinal chemistry teams to assemble peptides containing a proline-derived, conformationally restricted residue. The Boc protection pattern supports segment condensation and standard peptide coupling workflows, allowing the residue to be introduced as a defined amino acid unit within protected peptide fragments. The 3,4-dehydro motif is particularly valued for generating peptide backbones with altered geometry compared with saturated proline, enabling structure-activity relationship studies and backbone engineering in peptide drug discovery and chemical biology programs.
2. Peptidomimetic SAR Development
Boc-3,4-dehydroPro-OH serves as a key amino acid derivative for peptidomimetic design where researchers aim to emulate or modulate secondary-structure preferences using a dehydroproline scaffold. Medicinal chemistry and lead optimization teams incorporate this building block into analog series to evaluate how backbone rigidity and unsaturation influence target binding motifs and overall conformational behavior. Because the reagent is supplied as a protected, carboxylic acid building block, it integrates cleanly into established peptide intermediate pipelines used to generate libraries of analogs for SAR screening and mechanistic follow-up studies.
3. Protected Intermediate For Libraries
Boc-3,4-dehydroPro-OH is commonly employed in peptide library construction and intermediate manufacturing where reproducible, protected building blocks are required for parallel synthesis. Process chemists and peptide platform users rely on the Boc-protected amino functionality to manage compatibility with routine coupling and purification steps across multiple analogs, while the dehydroproline core provides a consistent structural element across the library. This makes the reagent a practical choice for generating defined peptide fragments and final constructs that incorporate unsaturated proline analogs for downstream characterization by LC-MS, HPLC, and NMR-based structural verification.
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