CAT No: CP26074
CAS No:850996-84-8
Synonyms/Alias:850996-84-8;AmbotzBAA1454;CTK5F4137;(2S,4R)-5-BENZYLOXYCARBONYLAMINO-2-TERT-BUTOXYCARBONYLAMINO-4-TRIISOPROPYLSILANYLOXY-PENTANOICACID;ZINC169909994;(2S,4R)-5-BENZYLOXYCARBONYLAMINO-2-T-BUTOXYCARBONYLAMINO-4-TRIISOPROPYLSILANYLOXY-PENTANOICACID;L-Ornithine,N2-[(1,1-dimethylethoxy)carbonyl]-N5-[(phenylmethoxy)carbonyl]-4-[[tris(1-methylethyl)silyl]oxy]-,(4R)-(9CI)
Chemical Name:(2S,4R)-5-Benzyloxycarbonylamino-2-t-butoxycarbonylamino-4-triisopropylsilanyloxy-pentanoic acid
Boc-L-Orn(4R-OTIPS, 5-Z)-OH is a protected, stereodefined ornithine derivative designed for downstream peptide and peptidomimetic synthesis, featuring a Boc-protected alpha-amino group and an OTIPS-protected side-chain at the 4-position. The (4R) configuration and the (5-Z) stereochemical specification make it a useful building block when defined geometry and side-chain stereochemistry are required for segment assembly, cyclization strategies, or constrained analog design. The OTIPS group provides temporary protection for the side-chain functionality during coupling and purification steps, supporting workflows that rely on orthogonal reactivity and controlled deprotection.
1. Peptide Segment Building
Boc-L-Orn(4R-OTIPS, 5-Z)-OH is used as a protected amino acid building block for custom peptide synthesis where ornithine-derived residues must be introduced with strict control over side-chain stereochemistry and alkene geometry. Peptide chemistry groups and contract peptide manufacturers typically select this type of protected derivative to ensure that the reactive amine and side-chain functionalities do not interfere with activation/coupling steps, enabling reliable incorporation into linear sequences or into segments destined for further functionalization. The Boc protection supports standard peptide assembly workflows, while the OTIPS-protected side chain helps maintain compatibility with purification and coupling conditions until the sequence is ready for targeted deprotection.
2. Stereodefined Peptidomimetics
Boc-L-Orn(4R-OTIPS, 5-Z)-OH supports peptidomimetic development programs that require defined (4R) stereochemistry and (5-Z) geometry to reproduce conformational preferences or to probe structure-property relationships. Medicinal chemistry and chemical biology teams often use stereochemically specified amino acid derivatives to build constrained analogs, including residues that later serve as handles for diversification after peptide assembly. In these workflows, the protected form is selected to preserve the integrity of the stereochemical features through segment condensation and to minimize side reactions during library synthesis, producing intermediates suitable for subsequent deprotection and downstream derivatization.
3. Pharmaceutical Intermediate Synthesis
Boc-L-Orn(4R-OTIPS, 5-Z)-OH is also positioned as a stereodefined intermediate for the preparation of ornithine-based fragments used in pharmaceutical intermediate development. Process and R&D chemists commonly rely on protected, geometry-controlled amino acid derivatives to construct advanced intermediates that later undergo functional group interconversions or coupling into larger scaffolds. The Boc and OTIPS protection pattern helps manage chemoselectivity during multi-step synthesis, allowing the intermediate to be carried through activation, purification, and coupling operations while protecting the key nucleophilic sites until the synthetic sequence reaches the appropriate stage for deprotection and conversion.
4. Orthogonally Protected Diversification
Boc-L-Orn(4R-OTIPS, 5-Z)-OH is frequently selected when a protected ornithine derivative is needed to enable controlled diversification after peptide or fragment assembly. Research groups designing stepwise functionalization strategies use side-chain protection to defer reactivity, allowing them to complete coupling and sequence assembly before exposing the side-chain functionality for subsequent transformations. The combination of Boc protection on the alpha-amino group and OTIPS protection on the side-chain supports staged workflows where intermediate handling, purification, and later derivatization must be performed without premature side reactions, improving the practicality of building stereochemically defined, functionalized products for further chemical biology or medicinal chemistry studies.
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