Boc-Asp(OcPent)-OH is a protected amino acid derivative of aspartic acid in which the α-amino group is masked as a Boc (tert-butoxycarbonyl) carbamate and the side-chain carboxyl group is esterified as an OcPent (pentyl ester), yielding a protected Asp building block for peptide-related synthesis. The molecule contains a Boc-protected amine, a pentyl-protected side-chain carboxyl, and a free C-terminal carboxylic acid (-CO2H), with the protected functionalities designed to suppress undesired side reactions during coupling steps while maintaining the acidic termini for controlled reactivity. In synthetic workflows, this compound is used as a stepwise amino acid precursor to assemble Asp-containing peptide sequences, where selective deprotection and subsequent coupling enable incorporation of the aspartate side-chain functionality under controlled conditions.
CAT No: CP27386
CAS No:71447-58-0
Synonyms/Alias:Boc-Asp(OcPn)-OH;BOC-ASP(OCPENT)-OH;Boc-L-asparticacid4-cyclopentylester;71447-58-0;ST51037520;AC1OCXN6;15074_ALDRICH;SCHEMBL5354817;15074_FLUKA;MolPort-003-926-630;ZINC2169523;6279AH;KM1407;AKOS024386372;(2S)-2-[(tert-butoxy)carbonylamino]-3-(cyclopentyloxycarbonyl)propanoicacid;(2S)-4-cyclopentyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoicacid
Boc-Asp(OcPent)-OH is a protected aspartic acid derivative featuring an N-terminal Boc protecting group and a side-chain carboxyl protected as an OcPent ester, providing controlled reactivity during peptide assembly. This protected amino acid building block is commonly selected when Asp residues require orthogonal side-chain protection to support reliable coupling and segment assembly in peptide synthesis workflows. The combination of a Boc-protected amino terminus with an ester-protected side chain helps manage chemoselectivity across subsequent deprotection and condensation steps used in research and custom peptide manufacturing.
1. Solid-Phase Peptide Synthesis
Boc-Asp(OcPent)-OH is used as an Asp building block in solid-phase peptide synthesis workflows where precise incorporation of aspartate side chains is required for peptide library construction and sequence-specific target peptides. The Boc group on the alpha-amino functionality supports standard peptide coupling strategies, while the OcPent side-chain ester protection helps minimize undesired side reactions from the Asp side-chain carboxyl during chain elongation. Researchers and peptide synthesis service providers frequently choose this protection pattern when they need robust handling of Asp-containing sequences without premature side-chain participation, especially for longer peptides or multistep segment assembly.
2. Aspartate Side-Chain Protection Strategy
Boc-Asp(OcPent)-OH is also applied in custom peptide manufacturing and medicinal chemistry intermediate preparation when a controlled Asp side-chain protection strategy is needed to enable selective downstream transformations. The OcPent ester protection is selected to keep the side-chain carboxyl masked under peptide coupling conditions, allowing the synthesis team to defer side-chain exposure until the appropriate deprotection stage. This makes the reagent particularly useful for preparing Asp-rich motifs, as well as for assembling peptides where the side-chain carboxyl must remain protected to avoid cross-reactions, aggregation-prone behavior, or side reactions that can complicate purification and characterization.
3. Peptide Segment Condensation
Boc-Asp(OcPent)-OH is frequently used in solution-phase peptide synthesis and segment condensation approaches where protected amino acid derivatives are required to maintain chemoselectivity between coupling partners. In these workflows, the Boc-protected amino functionality and the OcPent-protected side-chain carboxyl help ensure that the reactive sites are appropriately controlled to favor formation of the desired amide bond while limiting competing reactivity from the Asp side chain. Medicinal chemistry groups and process-oriented peptide developers use this building block to support the assembly of protected peptide fragments that can be further processed into full-length peptides with defined Asp side-chain availability at later steps.
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