Boc-D-Leu-OSu is a protected amino acid derivative in which D-leucine is converted to an activated N-Boc ester for peptide coupling applications. The molecule contains a tert-butoxycarbonyl (Boc) protecting group on the amino functionality and an OSu leaving group (succinimidyl ester) on the carboxyl side, with the D stereochemical configuration indicated by the "D" designation and the leucine isobutyl side chain providing a hydrophobic alkyl functionality. In synthesis, this activated ester form is employed as a precursor for forming amide bonds in peptide synthesis workflows, including steps where chemoselective coupling to an amine nucleophile is required under standard peptide chemistry conditions.
CAT No: CP27259
CAS No:60111-76-4
Synonyms/Alias:60079-51-8;(S)-2-Amino-2-phenylacetamidehydrochloride;H-Phg-NH2.HCl;L-Phenylglycineamidehydrochloride;H-Phg-NH2Hcl;H-PHG-NH2HCL;SCHEMBL1137429;CTK8B3704;LXOAFHGMXCFTOU-FJXQXJEOSA-N;MolPort-020-003-940;ANW-42970;KM0365;AKOS016003028;AM82656;AK-87810;TC-131715;FT-0698664;ST24035937;(alphaS)-alpha-amino-benzeneacetamidehydrochloride;J-300369;Benzeneacetamide,-amino-,hydrochloride(1:1),(S)-
Boc-D-Leu-OSu is a D-configured leucine derivative supplied as an N-hydroxysuccinimide (OSu) ester bearing a Boc-protecting group on the amino nitrogen. This combination makes it a practical activated amino acid building block for peptide coupling workflows where pre-activation improves segment condensation efficiency and reproducibility. The OSu leaving group supports ester-based acyl transfer under standard peptide synthesis conditions, while the Boc group provides stable protection of the amino functionality during downstream assembly.
1. Peptide Segment Coupling
Boc-D-Leu-OSu is frequently used for assembling D-amino-acid-containing peptides in custom peptide synthesis, including solution-phase workflows and segment condensation strategies where activated amino acid esters are preferred. Researchers developing peptides for structure-activity relationship studies or conformational control rely on this reagent to introduce D-Leu residues with consistent coupling performance, supporting streamlined synthesis of peptide fragments that are later joined to form longer sequences. The OSu activation pattern is particularly useful when coupling efficiency and minimizing side reactions are key priorities during iterative fragment assembly.
2. D-Leu-Containing Peptidomimetics
Boc-D-Leu-OSu supports the preparation of peptidomimetics and peptide-like scaffolds that incorporate D-leucine to modulate backbone stereochemistry and proteolytic stability in chemical biology programs. Medicinal chemistry groups and academic peptide labs commonly use activated amino acid esters to rapidly build defined analogs for SAR screening, where the ability to reliably install a single stereocenter is critical for comparing analog series. By providing a protected, activated leucine unit, this reagent fits into development pipelines that prioritize consistent building-block quality for downstream purification and characterization.
3. Pharmaceutical Intermediate Development
Boc-D-Leu-OSu is also used as a high-value intermediate building block in the preparation of D-amino-acid-containing intermediates for larger synthetic programs. Process development chemists and contract research organizations may select OSu-activated amino acid reagents to improve the practicality of forming amide linkages during intermediate construction, especially when the target route requires controlled handling of a Boc-protected amino functionality. This makes the reagent relevant to the synthesis of protected D-leucine derivatives and peptide-related intermediates used in specialty chemical manufacturing and scale-up planning.
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