Boc-cis-Hyp-OMe is a Boc-protected, cis-configured hydroxyproline derivative in which the amino acid backbone is esterified as the methyl ester (OMe). The molecule contains a tert-butoxycarbonyl (Boc) protecting group on the amino functionality and a carboxyl group masked as a methyl ester, while the side chain bears a hydroxyl group characteristic of hydroxyproline and the ring constraint supports a cis relationship between relevant stereochemical elements as indicated by the name. In peptide synthesis workflows, this protected amino acid ester is used as a stepwise building block to control chemoselectivity at the amine during coupling and to provide a hydroxyl-bearing residue for subsequent derivatization or incorporation into peptide-related intermediates.
CAT No: CP26140
CAS No:102195-79-9
Synonyms/Alias:102195-79-9;N-Boc-cis-4-hydroxy-L-prolinemethylester;(2S,4S)-1-tert-butyl2-methyl4-hydroxypyrrolidine-1,2-dicarboxylate;Boc-cis-Hyp-Ome;Boc-cis-4-Hydroxy-L-prolinemethylester;1-tert-Butyl2-Methyl(2S,4S)-4-Hydroxypyrrolidine-1,2-dicarboxylate;METHYLCIS-1-BOC-4-HYDROXY-L-PROLINATE;(2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylicacid1-tert-butylester2-methylester;N-(tert-Butoxycarbonyl)-cis-4-hydroxy-L-prolineMethylEster;O1-TERT-BUTYLO2-METHYL(2S,4S)-4-HYDROXYPYRROLIDINE-1,2-DICARBOXYLATE;1,2-PYRROLIDINEDICARBOXYLICACID,4-HYDROXY-,1-(1,1-DIMETHYLETHYL)2-METHYLESTER,(2S,4S)-;cis-Boc-Hyp-OMe;Boc-trans-4-Hydroxy-L-prolinemethylester;ZINC00403526;PubChem21950;BOC-CIS-L-HYP-OME;BOC-L-CIS-HYP-OME;SCHEMBL85695;KSC496S3F;654000_ALDRICH;CTK3J6932;MolPort-004-969-098;MZMNEDXVUJLQAF-YUMQZZPRSA-N;BH763;ZINC403526
Boc-cis-Hyp-OMe is a protected amino acid derivative built on cis-hydroxyproline, incorporating a Boc amino-protecting group and a methyl ester at the carboxyl terminus. This combination makes the compound a practical building block for controlled peptide assembly where the sterically constrained cis-hydroxyproline motif and protected functional groups are required for downstream coupling and segment condensation. In peptide chemistry and medicinal chemistry development, Boc-cis-Hyp-OMe is commonly handled as a stable, isolable intermediate that supports the preparation of hydroxyproline-containing peptides and peptidomimetic fragments.
1. Peptide Segment Building
Boc-cis-Hyp-OMe is used by peptide synthesis groups to construct hydroxyproline-containing peptide segments where the cis stereochemistry is a key structural element. The Boc protection on the amino function and the methyl ester at the C-terminus align with workflows that require a defined, protected residue for sequential coupling and later conversion into the appropriate peptide termini during assembly. Researchers developing collagen-mimetic peptides, proline- and hydroxyproline-rich motifs, and conformationally constrained peptide scaffolds rely on this type of protected cis-hydroxyproline building block to maintain stereochemical integrity through multistep synthesis.
2. Peptidomimetic Intermediate Development
Boc-cis-Hyp-OMe serves as a practical starting residue for medicinal chemistry teams preparing peptidomimetic fragments that incorporate cis-hydroxyproline as a conformational constraint. By carrying both an amino-protecting group and an esterified carboxyl group, the intermediate supports downstream functionalization strategies that convert the building block into coupling-ready fragments or further derivatized analogs used in structure-activity relationship studies. This is particularly relevant in programs where hydroxyproline stereochemistry and the presence of the side-chain hydroxyl are leveraged to tune local geometry and enable subsequent chemical elaboration.
3. Protected Amino Acid Coupling Blocks
Boc-cis-Hyp-OMe is routinely selected by custom peptide manufacturers and academic peptide cores as a protected amino acid coupling component for assembling defined sequences containing cis-hydroxyproline. The presence of the Boc group helps manage chemoselectivity during peptide assembly steps, while the ester form provides a handle for controlled downstream transformations of the residue's carboxyl functionality as the sequence grows. In practice, this derivative is used to generate hydroxyproline-containing intermediates that can be carried through segment condensation and purification workflows, supporting reliable synthesis of stereochemically defined peptide products.
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