Boc-L-aspartic acid β-allyl ester is a protected amino acid derivative in which L-aspartic acid bears a tert-butoxycarbonyl (Boc) protecting group on the α-amino group and an allyl ester at the β-carboxyl position. The molecule contains both a Boc-carbamate-protected amino functionality and a free α-carboxylic acid, while the β-side chain is modified from the native carboxylate to a β-allyl ester, providing an additional handle for orthogonal transformations and side-chain functionalization. In peptide synthesis and peptide-derivative preparation, this β-allyl ester form supports stepwise control of carboxyl reactivity and can be used as a precursor for generating aspartate side-chain derivatives that carry an allyl-derived functional group for further conjugation or structural studies.
CAT No: CP00410
CAS No:132286-77-2
Synonyms/Alias:Boc-Asp(OAll)-OH;132286-77-2;Boc-L-asparticacid4-allylester;AmbotzBAA1072;AC1Q1MRM;72814_ALDRICH;SCHEMBL17148005;72814_FLUKA;CTK8E6908;MolPort-003-938-765;C12H19N1O6;ZINC2564707;AKOS025294306;KB-48251;RT-011712;X5804;K-4150;N-(tert-Butoxycarbonyl)-L-asparticacid4-allylester;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-prop-2-enoxybutanoic acid;(S)-4-(Allyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid;N-alpha-t-Butyloxycarbonyl-L-aspartic acid beta-allyl ester;(2S)-2-[(TERT-BUTOXYCARBONYL)AMINO]-4-OXO-4-(PROP-2-EN-1-YLOXY)BUTANOIC ACID;Boc-L-aspartic acid 4-allyl ester;MFCD00273398;SCHEMBL17148005;DTXSID30563936;N-Boc-O4-allyl-L-aspartic acid;Boc-L-aspartic acid-b-allyl ester;Boc-Asp(OAll)-OH, >=98.0%;AKOS025294306;HY-W142109;BS-20666;CS-0201893;E72664;(S)-4-(allyloxy)-2-(tert-butoxycarbonylamino)-4-oxobutanoic acid;(2S)-2-[(tert-Butoxycarbonyl)amino]-4-oxo-4-[(prop-2-en-1-yl)oxy]butanoic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-oxo-4-(prop-2-en-1-yloxy)butanoic acid
Boc-L-aspartic acid β-allyl ester is an L-aspartate derivative bearing a Boc-protected alpha-amino group and a β-allyl ester on the side chain, providing an orthogonally masked carboxyl functionality commonly leveraged during peptide assembly. The allyl ester is designed for controlled deprotection under conditions compatible with peptide synthesis workflows, enabling selective side-chain carboxyl availability when building aspartate-containing sequences. This protected amino acid building block is therefore used by peptide chemists to manage side-chain reactivity while maintaining a protected backbone for coupling chemistry.
1. Solid-Phase Peptide Synthesis
Boc-L-aspartic acid β-allyl ester is used as a protected aspartate building block in custom peptide synthesis, particularly when side-chain carboxyl control is required during stepwise chain elongation. Peptide synthesis groups select the β-allyl ester to keep the aspartate side chain masked during coupling and deprotection cycles, then unmask it at the appropriate stage to support subsequent transformations or to enable formation of aspartyl linkages in longer constructs. The Boc-protected amino functionality supports its use in workflows where Boc-compatible protection strategies are employed for N-terminal handling and segment assembly.
2. Aspartate Side-Chain Functionalization
Boc-L-aspartic acid β-allyl ester is commonly chosen for preparing aspartate-containing intermediates where selective exposure of the β-carboxyl group is needed for downstream derivatization. Chemical biology and peptide-derivative development teams use this building block to introduce controlled modifications at the aspartate side chain after the peptide backbone has been assembled or partially assembled, supporting the generation of aspartate-functional peptide fragments used in structure-activity relationship studies and binding assay reagent development. The allyl ester protection pattern helps reduce undesired side reactions from the side-chain carboxyl during earlier synthetic steps.
3. Peptide Segment Coupling Intermediates
Boc-L-aspartic acid β-allyl ester is applied in the preparation of protected peptide segments and coupling-ready intermediates that incorporate aspartate residues with a masked β-carboxyl group. Contract peptide manufacturing and academic peptide chemistry laboratories use this type of protected amino acid when they need reliable control over functional-group compatibility across multi-step syntheses, including sequences where aspartate side-chain reactivity could otherwise interfere with coupling efficiency or purification. By maintaining orthogonal protection on the side chain, the building block supports efficient assembly of aspartate-rich peptides and fragments intended for subsequent conversion to fully deprotected targets.
4. Pharmaceutical Intermediate Development
Boc-L-aspartic acid β-allyl ester is also used as a defined, protected aspartate unit in the development of pharmaceutical intermediates and peptidomimetic precursors that require controlled unveiling of the β-carboxyl functionality at a later stage. Medicinal chemistry groups and specialty synthesis providers select this reagent when a protected aspartate motif must be carried through a sequence of transformations without premature activation or derivatization of the side chain. The Boc/β-allyl protection scheme supports staged functional group management, which is particularly valuable when assembling complex intermediates that contain multiple reactive sites.
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