Boc-L-tert.leucine

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

CAT No: CP07904

CAS No:62965-35-9

Synonyms/Alias:62937-47-7;(R)-2-Carbamoyl-1-N-Cbz-pyrrolidine;Z-D-PRO-NH2;(R)-2-Carbamoyl-1-Cbz-pyrrolidine;(R)-BENZYL2-CARBAMOYLPYRROLIDINE-1-CARBOXYLATE;(R)-2-carbamoyl-n-cbz-pyrrolidine;1-Pyrrolidinecarboxylicacid,2-(aminocarbonyl)-,phenylmethylester,(2R)-;AC1OCUST;663220_ALDRICH;SCHEMBL1437568;CTK5B6717;MolPort-002-041-513;ZINC399374;AB3071;ANW-72517;CZ-064;AJ-21730;AK-35919;N834;ZB012774;AB0016073;KB-209894;TC-161262;M-1615;benzyl(2R)-2-carbamoylpyrrolidine-1-carboxylate

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M.F/Formula
C13H16N2O3
M.W/Mr.
231.3

Boc-L-tert.leucine is an N-Boc-protected, L-configured tert-leucine amino acid building block designed for peptide and peptidomimetic synthesis where a sterically demanding, branched hydrophobic side chain is required. The tert-leucine residue provides increased steric bulk relative to standard leucine, supporting the preparation of constrained or lipophilic peptide segments. As an Fmoc-free, Boc-protected amino acid, it is typically selected for workflows that rely on Boc-compatible peptide coupling and subsequent deprotection/assembly strategies.

1. Boc-Based Peptide Synthesis

Boc-L-tert.leucine is used as a protected amino acid building block for constructing peptides and peptidomimetics in Boc-based synthetic workflows, including segment condensation and custom peptide manufacturing. Peptide chemists select this residue when they want to introduce the tert-leucine side chain to tune hydrophobic character and steric environment within a growing sequence. The Boc group on the amino terminus supports controlled stepwise assembly, enabling the tert-leucine unit to be incorporated as a defined, stereochemically consistent amino acid segment for downstream purification and characterization.

2. Steric Hydrophobic Residue Incorporation

Boc-L-tert.leucine is commonly employed in structure-activity relationship (SAR) studies and peptide optimization campaigns where side-chain bulk and hydrophobicity are key design variables. Medicinal chemistry groups use this building block to probe how increased steric demand from the tert-leucine moiety affects conformational preferences, local packing, and sequence-dependent behavior in peptide leads. This makes the reagent particularly useful for preparing focused analog libraries that compare leucine-like hydrophobic residues against more sterically congested variants, while keeping the backbone and stereochemistry consistent across analogs.

3. Peptidomimetic and Fragment Building

Boc-L-tert.leucine serves as a practical fragment component for preparing larger peptide-like molecules and intermediate segments in peptidomimetic development. Chemical biology and medicinal chemistry teams often incorporate tert-leucine to modulate the physicochemical profile of peptide fragments used in conjugation-ready or further derivatization-ready syntheses. Because the reagent is supplied as a protected amino acid, it integrates cleanly into stepwise synthetic planning for assembling complex sequences where orthogonal functional group handling and reliable downstream processing are required.

4. Pharmaceutical Intermediate Development

Boc-L-tert.leucine is also used as a defined amino acid intermediate in the manufacturing and development of peptide-derived intermediates for research and specialty chemical production. Process and development chemists value the reagent as a standardized, stereochemically defined building block for producing tert-leucine-containing intermediates that can be carried forward into subsequent coupling, protection/deprotection, or functionalization steps. This application is especially relevant when tert-leucine's branched hydrophobic side chain is needed as a controllable element in the intermediate's structure for later conversion into final peptide or peptidomimetic targets.

Abbr
Boc-Tle-OH
InChI
1S/C13H16N2O3/c14-12(16)11-7-4-8-15(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H2,14,16)/t11-/m1/s1
InChI Key
ZCGHEBMEQXMRQL-LLVKDONJSA-N
Canonical SMILES
C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C(=O)N

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