Boc-D-MeIle-OH is a protected, non-natural amino acid derivative featuring a tert-butoxycarbonyl (Boc) carbamate protecting group on the amino functionality and a D-configured 2-aminoisobutyric acid-like backbone bearing a methyl-substituted isoleucine side chain. The molecule contains a free carboxylic acid (-COOH) and a Boc-protected amine (-NH-C(O)O-tBu), with the side chain providing a branched alkyl environment that can influence hydrophobicity and steric effects during peptide assembly. In peptide chemistry, this Boc-protected amino acid is used as a building block for stepwise coupling and for preparing peptide intermediates in which temporary protection of the amine supports chemoselective formation of amide bonds.
CAT No: CP25689
CAS No:267223-87-0
Synonyms/Alias:Boc-D-MeIle-OH;267223-87-0;Boc-N-Me-D-Ile-OH;SCHEMBL1128243;CTK8E7306;MolPort-023-223-285;ZINC2560686;6341AH;AKOS024259145;AJ-40622;AK-89020;RT-011737;K-6872;(2R,3R)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylpentanoicacid
Chemical Name:N-alpha-(t-Butyloxycarbonyl)-N-alpha-methyl-D-isoleucine
Boc-D-MeIle-OH is a Boc-protected D-amino acid building block derived from D-2-amino-3-methylbutanoic acid, incorporating a branched hydrophobic side chain and a tert-butoxycarbonyl (Boc) group on the amino functionality. This protected stereodefined residue is commonly selected when peptide chemistry requires a D-configuration to tune local conformation, proteolytic stability, or stereochemical patterning in sequence-defined peptides. As a protected amino acid, it is primarily used as an input for peptide assembly rather than as a free amino acid reagent.
1. D-Peptide Building Block
Boc-D-MeIle-OH is used in custom peptide synthesis where incorporation of a D-configured, branched aliphatic residue is desired to modulate backbone geometry and resist enzymatic degradation. Research groups building stereochemically defined peptidomimetics, protease-stability variants, and D-amino-acid-enriched segments rely on Boc protection to maintain compatibility with peptide coupling workflows and to deliver the residue in a protected form suitable for controlled chain assembly. The MeIle side chain contributes hydrophobic character and steric bulk that can influence helix/turn propensity and local packing in short peptides and longer constructs.
2. Protected Residue For SPPS
Boc-D-MeIle-OH is frequently selected as a protected amino acid component for solid-phase peptide synthesis development and scale-up, especially in workflows that use Boc-based protection strategies. Peptide synthesis teams use this building block to introduce a stereochemically fixed D-residue at a specific position, supporting rapid generation of sequence libraries and analog series where stereochemistry is varied systematically. The Boc-protected amino group helps ensure that coupling proceeds from the intended functional handle during assembly, while the D-stereocenter provides consistent stereochemical outcomes across batch-to-batch peptide manufacturing and screening.
3. Peptidomimetic SAR Intermediates
Boc-D-MeIle-OH is applied in medicinal chemistry and chemical biology programs that prepare peptidomimetic scaffolds for structure-activity relationship (SAR) studies, particularly when D-amino-acid incorporation is used to tune conformation and metabolic stability profiles of peptide-like ligands. Medicinal chemistry groups use this residue to construct analogs where side-chain hydrophobicity and stereochemical placement are key variables, enabling downstream evaluation of binding or functional readouts in assay systems. In these workflows, the protected amino acid form supports reliable incorporation into lead-optimization candidates and facilitates parallel synthesis of multiple stereochemical variants.
4. Stereodefined Analog Libraries
Boc-D-MeIle-OH is used to generate stereodefined peptide or peptidomimetic analog libraries in which D-residue patterning is systematically explored to map structure-property relationships. Chemical biology and materials research groups often prepare panels of short, sequence-defined peptides to probe how stereochemistry and hydrophobic side-chain features affect aggregation, self-assembly, or surface interactions in biomolecular materials. The Boc-protected, D-configured nature of the building block supports reproducible incorporation during library synthesis, helping maintain consistent stereochemical identity across comparative experiments.
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