H-alpha-All-D-Ala-OH is an amino acid derivative featuring an N-terminal (H-alpha) alanine framework bearing an allophanate-type (All) modification and a carboxylic acid at the alanine α-position, with the second residue specified as D-alanine (D-Ala). The molecule contains both an amino functionality and a carboxyl group, while the All (allophanate) moiety introduces an additional carbamoyl-related linkage that can modulate reactivity and chemoselectivity during peptide-related transformations, with stereochemistry indicated by the D configuration at the alanine center. It is used as a defined building block or intermediate in peptide synthesis and related structure-activity studies where a D-alanine-containing segment and a controlled functional handle for stepwise coupling or derivatization are required.
CAT No: CP26116
CAS No:96886-55-4
Chemical Name:(S)-alpha-Allylalanine, (S)-2-Amino-2-methylpent-4-enoic acid (>98%, >98%ee)
H-alpha-All-D-Ala-OH is a chiral amino acid derivative featuring an L-configured alanine residue bearing an allophanate-derived amino acid motif and a D-alanine stereocenter, presented as a free carboxylic acid. The molecule contains primary amide and carboxylic acid functional groups that can participate in peptide coupling chemistry, while the stereochemical arrangement at the D-alanine center supports stereodefined incorporation into peptide frameworks and stereocontrolled SAR analogs. The presence of an amino-reactive nitrogen functionality together with a terminal acid enables conversion to protected amino acid derivatives, N-activated esters, or coupling-ready intermediates under standard peptide synthesis conditions. As a chiral amino acid intermediate, H-alpha-All-D-Ala-OH can serve as a downstream precursor for protected amino acid building blocks and for stereochemically defined peptide or peptidomimetic constructs.
1. Peptide Synthesis
H-alpha-All-D-Ala-OH is used in peptide synthesis workflows where stereodefined D-alanine incorporation is required to tune conformational preferences and proteolytic stability. The amino acid backbone with a free carboxylic acid supports conversion to coupling partners such as activated esters or protected acid derivatives, while the D-configuration enables controlled stereochemistry during sequential chain assembly. Allophanate-related nitrogen functionality can be leveraged as a protection strategy that may be orthogonally manipulated relative to side-chain or backbone protecting groups during peptide coupling and deprotection steps. Downstream peptide products prepared from H-alpha-All-D-Ala-OH can include D-Ala-containing segments for research-grade peptide libraries and stereochemically defined analog series.
2. Drug Discovery SAR Studies
H-alpha-All-D-Ala-OH is applicable to structure-activity relationship studies that require systematic variation of stereochemistry at amino acid positions to map binding-site tolerance. The defined D-alanine stereocenter and the amino acid functional groups enable incorporation into peptide mimetics, constrained turn-forming motifs, or backbone-modified scaffolds used in medicinal chemistry campaigns. The free carboxylic acid can be transformed into amide-forming derivatives for rapid analog generation, while the protected nitrogen element supports iterative synthesis of series with consistent chemotypes. Stereochemically controlled incorporation of D-Ala using H-alpha-All-D-Ala-OH supports downstream SAR workflows that rely on reproducible peptide analog construction and structure-defined chemical libraries.
3. Chemical Biology Labeling
H-alpha-All-D-Ala-OH can be employed in chemical biology research for preparing stereochemically defined peptide probes and labeling handles where D-amino acid content is used to modulate stability and reduce enzymatic degradation. The amino acid functionality allows formation of amide linkages to introduce reporter tags, affinity groups, or bioorthogonal moieties through standard coupling chemistry. The presence of a reactive carboxylic acid enables attachment to linker systems or conjugation scaffolds while maintaining the stereochemical identity of the D-alanine residue. Resulting labeled peptides or conjugates derived from H-alpha-All-D-Ala-OH can serve as defined reagents for studying protein interactions, substrate recognition, or biomolecular processing in biochemical assays.
4. Protected Amino Acid Chemistry
H-alpha-All-D-Ala-OH is suitable for protected amino acid synthesis planning because it contains both an amino-reactive nitrogen element and a carboxylic acid handle that can be selectively protected or activated. The stereodefined D-alanine center can be preserved through protection-group selection strategies that minimize racemization during downstream transformations to N-protected or C-terminal activated forms. Allophanate-related functionality provides a chemical platform for orthogonal deprotection logic when assembling multi-protecting-group peptide intermediates. Prepared derivatives from H-alpha-All-D-Ala-OH can function as chiral building blocks for iterative peptide construction, fine chemical synthesis, and stereocontrolled intermediate manufacturing.
5. Process Chemistry Intermediate
H-alpha-All-D-Ala-OH is relevant to process chemistry intermediate preparation where controlled stereochemistry and functional-group compatibility are required for scalable amino acid derivative routes. The molecule's carboxylic acid and amino functionality enable conversion into standardized coupling-ready intermediates, supporting manufacturing workflows that prepare peptide building blocks in batch or continuous fine chemical processes. The presence of a protected nitrogen motif can be integrated into protection/deprotection sequences designed to maintain stereochemical integrity across multiple steps. Downstream use of H-alpha-All-D-Ala-OH-derived intermediates can support the production of D-Ala-containing peptide fragments used in industrial peptide manufacturing and research-grade specialty chemical production.
6. Peptidomimetics Construction
H-alpha-All-D-Ala-OH is applicable to peptidomimetic construction where D-alanine residues are incorporated to adjust backbone geometry, hydrogen-bonding patterns, and resistance to proteolysis. The amino acid structure supports formation of amide bonds and can be adapted into side-chain-modified or backbone-constrained analogs through derivatization of the carboxylic acid and amino functionalities. Stereochemical definition at the D-alanine center helps maintain consistent three-dimensional presentation of functional groups in mimetic scaffolds. Peptidomimetics generated from H-alpha-All-D-Ala-OH can be used as chemically defined research tools for evaluating molecular recognition and for building stereochemically consistent analog series in applied medicinal chemistry.
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