Boc-D-Pro-OSu is a protected amino acid derivative in which D-proline is converted to an activated N-hydroxysuccinimide (OSu) ester while the amino group is masked as a Boc (tert-butoxycarbonyl) carbamate. The molecule contains a Boc-protected amino functionality and an OSu ester derived from the carboxyl group, bearing the cyclic proline side chain and the D stereochemical configuration as indicated by the D designation. Boc-D-Pro-OSu is used as a coupling reagent for amide-bond formation in peptide synthesis and bioconjugation workflows, where the OSu ester provides a carboxyl-activation handle for reaction with nucleophiles under conditions compatible with Boc-protected amino acid derivatives.
CAT No: CP25118
CAS No:102185-34-2
Synonyms/Alias:Boc-D-Pro-OSu;102185-34-2;N-(tert-Butoxycarbonyl)-D-prolineSuccinimidylEster;Boc-D-prolineN-hydroxysuccinimideester;N-T-boc-D-prolineN-hydroxysuccinimide*ester;C14H20N2O6;AC1LGYGF;B1142_SIGMA;SCHEMBL9893215;CTK8A9029;MolPort-003-940-391;ZINC399464;N-Boc-D-prolineSuccinimidylEster;ANW-14662;CB-907;MFCD00069687;AKOS015840742;AKOS015915183;RTR-000571;AK-81118;KB-281506;B3414;ST24046217;V1173;K-0290
Chemical Name:N-alpha-t-Butyloxycarbonyl-D-proline succinimidyl ester
Boc-D-Pro-OSu is a Boc-protected D-proline N-succinimidyl ester designed for peptide-coupling workflows where a pre-activated amino acid derivative is preferred. The D-stereochemistry and the proline ring constrain backbone geometry, while the Boc group provides an N-protection handle that is compatible with standard protected-amino-acid assembly strategies. As an N-hydroxysuccinimide ester, the activated carboxylate enables efficient amide bond formation with nucleophilic amines during peptide synthesis and related intermediate preparation.
1. Peptide Coupling Building Block
Boc-D-Pro-OSu is used by peptide chemists to introduce D-proline at defined positions during peptide synthesis, particularly when a pre-activated carboxylate is advantageous for segment coupling or rapid assembly. The succinimidyl ester activation supports direct reaction with an amine-containing partner to form the corresponding peptide bond under coupling conditions commonly used for protected amino acid derivatives. This format is frequently selected for preparing D-proline-containing peptides, including stereochemically defined analogs used in structure-activity relationship studies and peptide library synthesis where stereochemical fidelity matters.
2. D-Proline-Containing Intermediate Synthesis
Boc-D-Pro-OSu is also employed as a pharmaceutical-intermediate style building block to generate Boc-protected D-proline amide intermediates that can be carried forward into larger synthetic sequences. Process and development groups value the activated ester form because it can simplify downstream amide formation steps compared with converting a free carboxylic acid into an activated coupling intermediate in situ. The Boc protection on the nitrogen helps maintain orthogonality of functional groups during intermediate handling, making the reagent practical for assembling protected amide fragments used in custom peptide manufacturing and medicinal chemistry lead optimization.
3. Stereodefined Peptidomimetic Development
Boc-D-Pro-OSu is used in peptidomimetic and conformationally constrained scaffold development where incorporating D-proline contributes to defined backbone stereochemistry and ring-constrained conformations. Medicinal chemistry teams and chemical biology laboratories often rely on stereochemically specified amino acid derivatives to build analog series for mapping structure-property relationships, including analogs that incorporate non-proteinogenic stereochemical features. The activated OSu functionality enables efficient coupling to amine-bearing fragments, supporting iterative synthesis of D-proline-containing building blocks used to construct larger peptidomimetic structures.
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