Boc-Ala-ONp is an Nα-Boc-protected alanine ONp ester, where alanine is converted to the corresponding active ester of the carboxyl group with an ONp (p-nitrophenyl) leaving group. The molecule contains a tert-butoxycarbonyl carbamate protecting the amino functionality, while the carboxyl group is esterified as a p-nitrophenyl ester, providing a distinct electrophilic carbonyl for acyl-transfer chemistry; the stereochemical configuration at the alanine center is not specified in the name. Boc-Ala-ONp is used as a peptide-synthesis building block and acylating intermediate, supporting stepwise formation of amide bonds by enabling controlled transfer of the alanine acyl group under conditions compatible with Boc protection.
CAT No: CP26859
CAS No:2483-49-0
Synonyms/Alias:Boc-Ala-ONp;2483-49-0;Boc-L-alanine4-nitrophenylester;L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-,4-nitrophenylester;ZINC02575523;AC1ODWBD;15052_ALDRICH;SCHEMBL2390983;15052_FLUKA;MolPort-003-926-621;SUHFNHHZORGDFI-VIFPVBQESA-N;ZINC2575523;6262AH;SBB063971;N-Boc-L-Alanine4-nitrophenylester;AKOS015889859;VZ33187;AK170078;FT-0654618;K-6592;4-nitrophenyl(2S)-2-[(tert-butoxycarbonyl)amino]propanoate;(S)-2-tert-butoxycarbonylamino-propionicacid4-nitro-phenylester;(4-nitrophenyl)(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Boc-Ala-ONp is a Boc-protected alanine derivative supplied as an ONp (p-nitrophenyl) ester, combining an N-terminal carbamate protecting group with an activated carboxylate suitable for peptide-coupling workflows. The alanine side chain is non-functionalized, making this building block a straightforward choice for constructing short peptides and for preparing alanine-containing fragments with controlled N-terminus protection. The ONp ester format is commonly selected in peptide intermediate development because it provides a leaving group that can facilitate downstream amide bond formation under standard coupling conditions.
1. Peptide Fragment Coupling
Boc-Ala-ONp is frequently used by peptide synthesis groups to assemble alanine-containing segments where a Boc-protected N-terminus is required for orthogonal control during stepwise construction. Custom peptide manufacturers and academic peptide chemistry labs rely on ONp-activated esters to promote efficient amide bond formation when coupling to amine-bearing partners, enabling rapid preparation of protected peptide intermediates that can be carried forward into subsequent elongation steps. The combination of Boc protection and an activated ester makes it practical for building defined sequences while maintaining protection of the alanine amino functionality until the desired deprotection stage.
2. Short Peptide Synthesis
Boc-Ala-ONp supports the preparation of short, Boc-protected peptide targets and peptide standards where alanine residues are incorporated as building blocks with minimal side-chain complexity. Researchers developing peptide libraries or sequence-defined oligopeptides often select ONp esters to streamline fragment condensation, particularly when they want a reliable activated carboxylate format that integrates cleanly into protected-peptide workflows. Because alanine has a simple methyl side chain, this derivative is commonly used when the focus is on controlling peptide length and N-terminal protection rather than introducing additional side-chain chemistry.
3. Pharmaceutical Intermediate Building Blocks
Boc-Ala-ONp is also used in medicinal chemistry and process-oriented intermediate development to generate protected alanine amide intermediates that serve as precursors for larger peptide-like scaffolds or peptidomimetic fragments. Pharmaceutical intermediate teams value the protected Boc/N-terminal identity and the activated ONp ester functionality because these features help standardize downstream transformations that require formation of amide linkages while keeping the amino terminus protected. This makes Boc-Ala-ONp a practical reagent when developing scalable routes to protected building blocks used in lead optimization and specialty synthesis campaigns.
4. Protected Alanine Reference Materials
Boc-Ala-ONp is employed in analytical and method-development contexts to prepare defined protected alanine-containing reference materials and coupling controls used during peptide chemistry troubleshooting. Laboratories performing routine optimization of coupling steps, monitoring reagent reactivity, or validating purification workflows may use this derivative to generate consistent, Boc-protected alanine amide products for characterization by HPLC, LC-MS, or NMR. The presence of a well-defined protecting group pattern and an activated ester handle supports reproducible intermediate generation, which is helpful for comparing coupling outcomes across batches and conditions.
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