Ac-Asp(OtBu)-OH is an N-acetylated, side-chain tert-butyl ester-protected derivative of aspartic acid, featuring a backbone amino acid framework with a free carboxylic acid at the C-terminus. The molecule contains an acetyl-protected α-amino group and a side-chain carboxyl group masked as an OtBu (tert-butyl ester), with stereochemistry not specified in the name. This protected amino acid is used as a precursor in stepwise peptide synthesis and related derivative preparation, where the protecting groups help control chemoselectivity by reducing undesired amide or ester formation at the side-chain carboxyl during coupling.
CAT No: CP26227
CAS No:117833-18-8
Synonyms/Alias:117833-18-8;Ac-Asp(OtBu)-OH;(S)-2-Acetamido-4-(tert-butoxy)-4-oxobutanoicacid;1026951-84-7;N-Acetyl-L-asparticacid4-tert-butylester;Acetyl-L-asparticacidbeta-tert-butylester;Ac-Asp-OtBu;SCHEMBL11912121;CTK8B2976;MolPort-020-004-759;ZINC2560338;0655AA;ANW-41535;AKOS015908295;AKOS016002311;AJ-40554;AK-42415;AK105066;AM007427;KB-211046;RT-011183;FT-0686498;ST24035918;Z5608;B-6526
Ac-Asp(OtBu)-OH is an N-acetylated aspartic acid derivative bearing an O-tert-butyl protected side-chain carboxyl group, supplied as a carboxylic acid building block for peptide and peptidomimetic synthesis workflows. The N-acetyl group provides an amide-capped amino terminus, while the OtBu ester protection helps control side-chain reactivity during coupling and subsequent assembly steps. This protected, pre-functionalized Asp unit is commonly selected when a defined aspartyl residue environment is required in synthetic segments or intermediates.
1. Peptide Segment Assembly
Ac-Asp(OtBu)-OH is used in peptide synthesis to incorporate an aspartyl residue with a protected side-chain carboxyl group, enabling controlled formation of aspartate-containing sequences without premature side reactions. Custom peptide synthesis groups and peptide chemistry labs often choose this building block when they need an N-acetylated residue context and a side-chain carboxyl that is stable under standard coupling conditions used for segment condensation or stepwise assembly. The OtBu protection supports downstream handling where selective deprotection and continuation of chain elongation are required to reach the intended aspartate functionality in the final peptide.
2. Aspartate Side-Chain Control
Ac-Asp(OtBu)-OH supports workflows that require precise management of the Asp side-chain carboxyl during intermediate preparation, such as generating defined aspartate-containing fragments for further derivatization. Medicinal chemistry and peptidomimetic development teams frequently use this type of protected amino acid derivative to keep the side-chain from participating in side reactions during coupling, purification, and subsequent synthetic transformations. The N-acetylated amino terminus also helps standardize the residue's chemical environment across a library of related analogs, which is valuable when comparing structure-property relationships in peptide-based research.
3. Pharmaceutical Intermediate Development
Ac-Asp(OtBu)-OH is applied as a protected amino acid intermediate for constructing aspartate-bearing synthetic intermediates used in the preparation of peptide-like scaffolds and related specialty chemicals. Process development and industrial R&D teams often rely on such protected building blocks to improve synthetic robustness by temporarily masking reactive functionality and enabling predictable downstream conversion when the protected group is removed at a later stage. This makes Ac-Asp(OtBu)-OH a practical choice for manufacturing-oriented routes where controlled functional group presentation is needed for consistent intermediate quality.
4. Protected Residue Standardization
Ac-Asp(OtBu)-OH is also used in analytical and method-development settings where standardized protected Asp residues are required as reference materials for confirming synthetic outcomes, monitoring derivatization steps, or validating peptide fragment identity. Peptide analytics laboratories may incorporate this building block into calibration or verification workflows for fragment-level characterization, especially when the target analytes contain an aspartate side-chain that must remain protected during sample preparation. By providing a defined N-acetylated, OtBu-protected aspartyl unit, it helps ensure that observed signals correspond to the intended protecting-group pattern rather than a mixture of partially deprotected species.
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