Boc-L-Pyr-OEt

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP25356

CAS No:144978-12-1

Synonyms/Alias:boc-pyr-oet;144978-12-1;(s)-ethyl-n-boc-pyroglutamate;N-Boc-L-pyroglutamicacidethylester;1-Boc-L-Pyroglutamicacidethylester;Boc-L-Pyroglutamicacidethylester;(S)-1-TERT-BUTYL2-ETHYL5-OXOPYRROLIDINE-1,2-DICARBOXYLATE;(S)-5-OXO-PYRROLIDINE-1,2-DICARBOXYLICACID1-TERT-BUTYLESTER2-ETHYLESTER;1,2-Pyrrolidinedicarboxylicacid,5-oxo-,1-(1,1-dimethylethyl)2-ethylester,(2S)-;1-(tert-butyl)2-ethyl(S)-5-oxopyrrolidine-1,2-dicarboxylate;AC1NUUBP;PubChem12120;BOC-L-PYR-OET;EthylBoc-L-pyroglutamate;EthylN-Boc-L-pyroglutamate;(S)-N-alpha-t-Butyloxycarbonyl-pyroglutamicacidethylester;EthylN-Boc(S)-pyroglutamate;SCHEMBL903617;(s)-ethyln-boc-pyroglutamate;UPCMLD00WCRH2-043;PYR231;Jsp002635;1-TERT-BUTYL2-ETHYL(2S)-5-OXOPYRROLIDINE-1,2-DICARBOXYLATE;N-Boc-L-pyroglutamicAcidEthyl;MolPort-000-002-216

Chemical Name:(S)-N-alpha-t-Butyloxycarbonyl-pyroglutamic acid ethyl ester

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M.F/Formula
C12H19NO5
M.W/Mr.
257,29 g/mole

Boc-L-Pyr-OEt is a protected L-amino acid derivative featuring a Boc-protected amino group and an ethyl ester at the carboxyl terminus, providing a stable, isolable building block for peptide and peptidomimetic assembly. The pyrrolidine ring side chain (proline-type architecture) makes this reagent a common choice for constructing conformationally constrained sequences where the cyclic backbone influences geometry and turn propensity. With both termini protected, Boc-L-Pyr-OEt is primarily used as a synthetic intermediate rather than a direct biochemical reagent.

1. Solid-Phase Peptide Coupling

Boc-L-Pyr-OEt is used by peptide synthesis groups to prepare proline-containing segments and to support stepwise sequence assembly in solid-phase workflows, where controlled protection and esterification help manage coupling and purification demands. Custom peptide manufacturers and academic peptide cores often rely on such protected amino acid derivatives to streamline intermediate handling and to reduce variability during segment condensation. The Boc group supports standard Boc-compatible peptide strategies, while the ethyl ester form is selected to maintain the carboxyl functionality in a protected, reaction-ready state during downstream transformations.

2. Solution-Phase Segment Condensation

Boc-L-Pyr-OEt is frequently employed in solution-phase peptide synthesis and segment coupling strategies to introduce a proline residue under controlled reactivity conditions. Medicinal chemistry teams developing peptide-like leads use this type of protected amino acid derivative when they need reliable conversion of the carboxyl functionality into an activated coupling partner during assembly of longer fragments. The combination of Boc protection and an ethyl ester provides a practical balance between stability for storage/handling and functional group availability for conversion into the appropriate coupling form during fragment condensation.

3. Peptidomimetic Intermediate Building Block

Boc-L-Pyr-OEt serves as a practical starting building block for peptidomimetic and constrained scaffold synthesis, particularly where a proline-like cyclic motif is incorporated to influence conformational behavior in non-natural analogs. R&D groups in chemical biology and pharmaceutical intermediate development use this reagent to construct protected intermediates that can be further elaborated into amide-linked structures or advanced coupling-ready derivatives. The protected amino and ester termini help maintain chemoselectivity during multi-step synthesis, enabling efficient progression toward larger, sequence-defined or scaffold-defined targets.

4. Pharmaceutical Intermediate Development

Boc-L-Pyr-OEt is also used as a specialty intermediate in the manufacturing supply chain for peptide-derived or peptide-inspired compounds, where consistent protected building blocks reduce process complexity. Process chemists and contract development organizations select Boc-protected amino acid esters to support reproducible downstream transformations during route scouting and scale-up of intermediate libraries. The defined protection pattern supports predictable handling through purification and conversion steps needed to reach final coupling or elaboration stages in larger synthetic sequences.

Size
0;
InChI
1S/C12H19NO5/c1-5-17-10(15)8-6-7-9(14)13(8)11(16)18-12(2,3)4/h8H,5-7H2,1-4H3/t8-/m0/s1
InChI Key
YWWWGFSJHCFVOW-QMMMGPOBSA-N
Canonical SMILES
CCOC(=O)C1CCC(=O)N1C(=O)OC(C)(C)C

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