Boc-Asp-OFm is a protected aspartic acid derivative in which the α-amino group is masked with a Boc (tert-butoxycarbonyl) protecting group and the side-chain carboxylic acid is converted to an O-Fm ester (Fm denotes a formyl-type ester protecting group). The molecule contains a Boc-carbamate-protected amino functionality and an esterified side-chain carboxyl group, while retaining a carboxyl group at the α-position, enabling controlled chemoselectivity during peptide coupling and minimizing side reactions from the side-chain carboxylate. Boc-Asp-OFm is used as a stepwise building block for peptide synthesis and for preparing aspartate-containing peptide derivatives where orthogonal protection of the side-chain carboxyl group supports sequential assembly and downstream deprotection strategies.
CAT No: CP26291
CAS No:129046-87-3
Synonyms/Alias:Boc-Asp-Ofm;129046-87-3;(S)-4-((9H-Fluoren-9-yl)methoxy)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoicacid;(3s)-3-[(tert-butoxycarbonyl)amino]-4-(9h-fluoren-9-ylmethoxy)-4-oxobutanoicacid(non-preferredname);(3S)-3-[(TERT-BUTOXYCARBONYL)AMINO]-4-(9H-FLUOREN-9-YLMETHOXY)-4-OXOBUTANOICACID;BA-beta-Fme;AC1L4UHM;AC1Q5XO0;SCHEMBL8350965;KST-1A1574;ZINC2517111;6282AH;AR-1A4483;N-alpha-tert-Butyloxycarbonylasparticacidbeta-fluorenylmethylester;AKOS024260769;AJ-37025;AK154817;AM003456;AM014357;AN-32422;Nalpha-Boc-asp-beta-fluorenylmethylester;FT-0686526;3B3-062073;N-Boc-L-Asparticacid1-(9H-fluoren-9-ylmethyl)ester;1-(9H-Fluoren-9-ylmethyl)N-((1,1-dimethylethoxy)carbonyl)-L-aspartate
Boc-Asp-OFm is a protected aspartic acid derivative designed for peptide synthesis workflows, combining an N-terminal Boc protecting group with an aspartate side-chain protected as a formyl ester (OFm). This protection pattern supports controlled handling of the acidic side chain during assembly of peptide segments, enabling reliable downstream deprotection and coupling strategies. The molecule's carboxylate functionality is masked as an OFm ester, which helps maintain compatibility with common peptide-building conditions while preserving the reactive backbone for stepwise synthesis.
1. Solid-Phase Peptide Synthesis
Boc-Asp-OFm is used by peptide synthesis groups to incorporate an aspartate residue into peptide sequences where side-chain carboxyl protection is required to prevent undesired side reactions during chain assembly. Researchers preparing peptide libraries and sequence-defined peptides rely on the OFm side-chain protection to keep the acidic functionality controlled throughout iterative coupling and deprotection cycles. The Boc-protected amino terminus supports segment condensation strategies that sequence assembly teams routinely apply when building Asp-containing motifs for biochemical studies, structure-activity relationship work, and custom peptide manufacturing.
2. Aspartate Side-Chain Functional Control
Boc-Asp-OFm is frequently selected when the aspartate side chain must remain protected until a planned stage in the synthesis or intermediate preparation workflow. Peptide chemists use this derivative to manage the reactivity of the additional carboxyl group on Asp, improving the practicality of assembling longer or more complex sequences that would otherwise be prone to side reactions from unprotected acidic groups. This controlled protection approach is particularly relevant for generating Asp-containing intermediates that later undergo standardized deprotection and subsequent transformations, supporting reproducible production of peptide targets used in chemical biology and protein research.
3. Pharmaceutical Intermediate Development
Boc-Asp-OFm is also applied in medicinal chemistry and pharmaceutical intermediate development as a protected amino acid building block for constructing aspartate-containing fragments and peptidomimetic scaffolds. Process development teams and synthetic chemistry groups use this type of protected Asp derivative to manage functional-group compatibility across multi-step routes, especially when acidic groups must be masked during key bond-forming steps. The defined protection pattern helps streamline downstream conversion to the corresponding free carboxylic acid or activated derivative at a late stage, aligning with common development workflows for peptide-like intermediates and specialty building blocks.
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