Boc-L-Pyr-OH*DCHA is a protected amino acid derivative consisting of L-pyrrolidine-2-carboxylic acid bearing a Boc (tert-butoxycarbonyl) carbamate protecting group on the amino functionality, with the carboxyl group present as a free acid. The molecule contains a secondary cyclic amine within the pyrrolidine ring and a Boc-protected nitrogen, and the "*DCHA" notation indicates formation of a dicyclohexylamine (DCHA) salt associated with the carboxylate. In peptide and amino acid synthesis workflows, the Boc protection and salt form help control chemoselectivity by reducing undesired amine reactivity while the free carboxylic acid serves as a coupling handle for preparing further amino acid and peptide derivatives.
CAT No: CP25875
CAS No:53100-44-0
Synonyms/Alias:BOC-PYR-OH;53100-44-0;(S)-Boc-5-oxopyrrolidine-2-carboxylicacid;N-Boc-L-pyroglutamicacid;1-(tert-butoxycarbonyl)-5-oxo-l-proline;Boc-L-pyroglutamicacid;(S)-1-(tert-butoxycarbonyl)-5-oxopyrrolidine-2-carboxylicacid;(2S)-1-[(tert-butoxy)carbonyl]-5-oxopyrrolidine-2-carboxylicacid;BocPyr;Boc-pyroglutamicacid;Boc-L-Pyr-OH;AmbotzBAA1312;PubChem12123;N-Boc-pyroglutamicacid;AC1L2WQX;AC1Q5XOH;N-Boc-L-glutamicAcidLactam;SCHEMBL1256527;CTK8C6265;(-)-1-Boc-L-pyroglutamicacid;1,2-Pyrrolidinedicarboxylicacid,5-oxo-,1-(1,1-dimethylethyl)ester,(2S)-;MJLQPFJGZTYCMH-LURJTMIESA-N;MolPort-002-345-637;KST-1B5072;ACT00026
Chemical Name:N-alpha-t-Butyloxycarbonyl-L-pyroglutamic acid dicyclohexylamine
Boc-L-Pyr-OH*DCHA is a Boc-protected L-pyrrolidine-2-carboxylic acid (pyrrolidine amino acid) supplied as a DCHA salt, combining a base-stable, Boc-protected amino acid building block with improved handling characteristics for synthesis workflows. The Boc group provides an N-protection strategy commonly used in peptide and peptidomimetic assembly, while the pyrrolidine side-chain offers a conformationally constrained, cyclic amine environment that is frequently leveraged in medicinal chemistry and structure-activity relationship studies. This form is typically selected when a protected amino acid intermediate is needed with reliable downstream coupling performance and convenient reagent handling.
1. Peptidomimetic Building Block
Boc-L-Pyr-OH*DCHA is used by medicinal chemistry and peptide-chemistry teams to construct peptidomimetic scaffolds where a cyclic, conformationally restricted side chain is advantageous for tuning shape and local stereoelectronic properties. The Boc-protected amino acid format supports stepwise assembly into amide-linked sequences, enabling rapid iteration of analog libraries for SAR studies, lead optimization, and structure-guided design. The DCHA salt form is often chosen to improve practical weighing, transfer, and consistency in automated or semi-automated synthesis workflows that rely on solid, well-behaved building blocks.
2. Protected Amino Acid Intermediate
Boc-L-Pyr-OH*DCHA serves as a protected amino acid intermediate for custom peptide synthesis and specialized fragment coupling in both academic and industrial research settings. Teams developing non-natural or constrained amino acid-containing sequences rely on the Boc-protection strategy to control chemoselectivity during sequential bond formation and to prepare defined intermediates for later deprotection and condensation steps. Because the product is supplied as a salt, it is frequently incorporated into routine building-block procurement plans where reproducibility of physical handling and batch-to-batch consistency are important for downstream synthesis of modified peptides and analogs.
3. Peptide Library Synthesis
Boc-L-Pyr-OH*DCHA is commonly incorporated into peptide library synthesis workflows aimed at generating focused sets of cyclic-amino-acid-containing variants. Researchers use the Boc-protected form to standardize the N-protection state across library members, while the pyrrolidine side chain contributes a constrained geometry that can influence conformational preferences and sequence-dependent properties. This makes the reagent a practical choice for parallel synthesis campaigns where multiple analogs must be assembled efficiently and carried forward into purification and characterization pipelines with minimal variability in protected building-block identity.
4. Pharmaceutical Intermediate Development
Boc-L-Pyr-OH*DCHA is also used in pharmaceutical intermediate development for preparing defined, protected amino acid fragments that later feed into larger synthetic routes toward peptide-like or constrained amide-containing targets. Process and synthesis teams value the protected amino acid format because it allows controlled incorporation of the cyclic amino acid unit at a specific stage of the overall sequence assembly. The DCHA salt form is frequently selected to support reliable solid-state handling and consistent reagent dosing during scale-up or intermediate manufacturing steps where workflow robustness matters.
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