Boc-L-MeNle-OH

Boc-L-MeNle-OH is an Nα-Boc-protected amino acid derivative featuring the L-amino acid backbone of MeNle (N-methyl norleucine), a non-proteinogenic, methylene-extended aliphatic side chain bearing an N-methyl substitution. The molecule contains a Boc carbamate at the amino terminus and a free carboxylic acid group, with the side chain functioning as a hydrophobic alkyl substituent that can modulate peptide conformations and packing when incorporated into peptide structures. It is used as a protected amino acid building block in peptide synthesis workflows, where the Boc group supports chemoselective coupling at the carboxylate/activated ester stage while enabling stepwise assembly of amino acid sequences or analogues for structure-activity and chemical biology studies.

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

CAT No: CP25196

CAS No:117903-25-0

Synonyms/Alias:117903-25-0;Boc-Menle-Oh;(S)-2-((tert-Butoxycarbonyl)(methyl)amino)hexanoicacid;Boc-N-Me-Nle-OH;Boc-L-MeNle-OH;AmbotzBAA5810;Boc-N-methyl-L-norleucine;AC1Q2UO6;L-Norleucine,N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-;SCHEMBL66398;N-Boc-N-methyl-L-norleucine;TMA043;CTK4B0488;Boc-N-Me-L-2-aminohexanoicacid;HYGQYTQHPSQSFF-VIFPVBQESA-N;MolPort-006-705-955;ZINC2526287;AKOS015836724;AJ-37587;AK-49291;KB-300023;RT-011774;FT-0689527;ST24035836;N-(tert-butoxycarbonyl)-N-methyl-L-norleucine

Chemical Name:N-alpha-t-Butyloxycarbonyl-N-alpha-methyl-L-norleucine

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

Boc-L-MeNle-OH is a Boc-protected L-amino acid building block featuring a non-proteinogenic, branched side chain derived from MeNle (methyl-substituted norleucine). As a protected amino acid, it is designed for peptide synthesis workflows where the N-terminus is masked by the Boc group while the side-chain and carboxyl functionality are positioned for downstream coupling strategies. This reagent is commonly selected by peptide chemists seeking a hydrophobic, sterically defined residue for structure-activity relationship (SAR) studies and for improving the chemical handle consistency across peptide fragments.

1. Peptide Synthesis Building Block

Boc-L-MeNle-OH is used as an amino acid building block in custom peptide synthesis, including both academic and industrial peptide manufacturing settings, where a Boc-protected residue is required for controlled fragment assembly. The MeNle side chain provides a hydrophobic, non-natural amino acid character that is frequently incorporated into peptide sequences to tune local sterics and side-chain packing during SAR campaigns. Because the N-terminus is protected, this material supports reliable incorporation into peptide intermediates under standard peptide coupling and deprotection workflows used for Boc-based strategies.

2. Peptidomimetic SAR Development

Boc-L-MeNle-OH is frequently employed in medicinal chemistry programs that develop peptidomimetics and non-natural peptide analogs for lead optimization. Researchers use this residue to introduce a methylated hydrophobic side chain that can modulate conformational preferences and improve the chemical diversity of analog libraries without changing the peptide backbone architecture. In practical development pipelines, the Boc protection pattern helps maintain compatibility with iterative fragment coupling and purification schemes, enabling systematic comparison of analogs where MeNle content is varied.

3. Pharmaceutical-Grade Intermediate Preparation

Boc-L-MeNle-OH serves as a practical protected amino acid intermediate for downstream synthesis of larger peptide fragments and advanced intermediates used in pharmaceutical intermediate development. Process chemists and peptide development teams value protected amino acid reagents for their predictable reactivity profile and for reducing variability during scale-up of peptide assembly steps. The Boc-protected format supports integration into controlled synthetic sequences that generate well-defined peptide intermediates for subsequent coupling, purification, and final assembly into target peptide structures.

Size
1 g;5 g;25 g;
InChI
1S/C12H23NO4/c1-6-7-8-9(10(14)15)13(5)11(16)17-12(2,3)4/h9H,6-8H2,1-5H3,(H,14,15)/t9-/m0/s1
InChI Key
HYGQYTQHPSQSFF-VIFPVBQESA-N
Canonical SMILES
CCCCC(C(=O)O)N(C)C(=O)OC(C)(C)C

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