Boc-D-MeLeu-OH

Boc-D-MeLeu-OH is a protected amino acid derivative in which the amino group of D-2-amino-3-methylleucine is masked as a tert-butoxycarbonyl (Boc) carbamate, while the carboxyl group remains present as a free acid (-CO2H). The side chain contains a branched alkyl functionality characteristic of the MeLeu residue, and the molecule bears the stereochemical designation "D" as specified by the product name. As a Boc-protected amino acid, it is used as a building block for stepwise peptide synthesis and for preparing more complex amino acid derivatives where temporary protection of the α-amino functionality supports controlled coupling chemistry.

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

CAT No: CP26092

CAS No:89536-84-5

Synonyms/Alias:Boc-N-methyl-D-leucine;Boc-N-Me-D-Leu-OH;89536-84-5;(2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoicacid;AmbotzBAA1220;Boc-Nalpha-methyl-D-leucine;SCHEMBL69223;TMA026;02677_FLUKA;CTK6A4221;MolPort-003-925-255;YXJFAOXATCRIKU-SECBINFHSA-N;ZINC1576261;ANW-39318;KM2848;AKOS015836739;N-tert-butoxycarbonyl-N-methyl-D-leucine;AJ-27319;AK-43413;AM037462;n-(tert-butoxycarbonyl)-n-methyl-d-leucine;TC-128063;FT-0655757;X6991;I14-3523

Chemical Name:N-alpha-(t-Butyloxycarbonyl)-N-alpha-methyl-D-leucine

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M.F/Formula
C12H23NO4
M.W/Mr.
245,32 g/mole

Boc-D-MeLeu-OH is a Boc-protected D-configured amino acid building block featuring a branched, hydrophobic side chain characteristic of MeLeu (methyl-substituted leucine). As a protected amino acid, it is designed for incorporation into peptide sequences under standard Boc-based synthetic workflows, where the N-terminus is protected by the tert-butoxycarbonyl group while the carboxylic acid remains available for activation/condensation. Its stereochemical fidelity and side-chain sterics make it a practical choice for preparing peptides and peptidomimetic segments that require D-amino acid content and hydrophobic residue patterning.

1. Boc-Based Peptide Synthesis

Boc-D-MeLeu-OH is used by peptide synthesis groups to assemble D-amino-acid-containing sequences via Boc-protected chemistry, enabling controlled incorporation of a stereochemically defined residue at specific positions. Custom peptide manufacturers and academic peptide labs commonly select this building block when they need a hydrophobic, branched MeLeu side chain to tune peptide conformation, aggregation tendency, or overall physicochemical character in the final sequence. Because the amino functionality is protected as Boc, the reagent fits routine peptide assembly workflows where stepwise deprotection and coupling are used to build defined peptide segments.

2. D-Amino Acid Segment Design

Boc-D-MeLeu-OH supports the development of D-enriched peptide segments used in structure-function studies and peptidomimetic design programs. Medicinal chemistry and chemical biology teams often employ D-amino acid residues to probe how stereochemistry and side-chain branching affect folding preferences, local backbone geometry, and resistance to enzymatic processing in experimental systems. In these workflows, the MeLeu side chain provides a hydrophobic, sterically informative residue that can be positioned to influence peptide surface properties and intramolecular packing within the assembled construct.

3. Pharmaceutical Intermediate Building Block

Boc-D-MeLeu-OH is also used as a defined chiral amino acid intermediate for downstream synthesis of peptide-like intermediates and specialty compounds that require a D-MeLeu motif. Process development and specialty chemical manufacturing groups rely on Boc-protected amino acid building blocks to maintain stereochemical integrity through multi-step routes, especially when the N-terminus must remain masked until late-stage coupling or derivatization. The reagent's protected amino functionality and stable, isolable form make it practical for preparing well-defined intermediates that can be carried into segment condensation or further functional transformations during custom synthesis campaigns.

4. Analytical Reference Peptide Synthesis

Boc-D-MeLeu-OH is frequently incorporated into reference peptide standards used for method development and characterization in peptide analytics. Analytical chemistry laboratories and proteomics method developers may synthesize defined D-amino-acid-containing peptide targets to support LC-MS/MS method optimization, retention-time mapping, and fragmentation behavior assessment for peptides containing branched hydrophobic residues. By enabling a precise MeLeu stereochemical pattern within a peptide standard, the building block helps ensure that analytical workflows evaluate the correct structure rather than relying on unlabeled or structurally ambiguous analogs.

Size
5 g;25 g;
InChI
1S/C12H23NO4/c1-8(2)7-9(10(14)15)13(6)11(16)17-12(3,4)5/h8-9H,7H2,1-6H3,(H,14,15)/t9-/m1/s1
InChI Key
YXJFAOXATCRIKU-SECBINFHSA-N
Canonical SMILES
CC(C)CC(C(=O)O)N(C)C(=O)OC(C)(C)C

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