D-Asparagine monohydrate is the D-stereoisomer of asparagine, an unprotected proteinogenic amino acid featuring a side chain with a primary amide (-CH2-CONH2) attached to the α-carbon. The molecule contains both an amino group and a carboxyl group, and the "monohydrate" form indicates association with one equivalent of water in the solid state while retaining the amino acid's zwitterionic character in solution. It is used as a defined amino acid building block for peptide and amide bond synthesis where the D-configuration is required, as well as for chemical biology and analytical studies involving stereochemical control of asparagine-containing structures.
CAT No: CP00301
CAS No:5794-24-1
Synonyms/Alias:5794-13-8;l-Asparaginemonohydrate;l-asparaginehydrate;L(+)-Asparaginemonohydrate;Asparaginemonohydrate;(S)-2,4-diamino-4-oxobutanoicacidhydrate;L-Asparticacid4-amide;(S)-(+)-2-Aminosuccinamicacid;UNII-2PD79VF521;L-(+)-AsparagineMonohydrate;(S)-2-Aminosuccinicacid4-amide;C4H8N2O3.H2O;Aminoplasmal;Normofundin;Nutrifundin;Thomaeamin;Asparagine(NF);L-Asparagin-1-wasser;AC1Q5IYB;H-Asn-OH??H2O;L-Asparagine,monohydrate;AC1L55GR;Asparagine,monohydrate,L-;SCHEMBL50255;KSC491M6D
D-Asparagine monohydrate is the D-stereoisomer of the proteinogenic amino acid asparagine, present as a hydrate form that can influence handling and gravimetric dosing in synthesis workflows. The molecule contains a stereogenic center at the α-carbon, a primary amide side chain (-CH2-CONH2), and a carboxamide/amide-rich functional landscape that supports hydrogen bonding and strong solvation interactions. The amino acid's bifunctional character enables conversion into protected amino acid derivatives and subsequent amide-forming peptide bond construction under standard coupling chemistries. The D-configuration makes it a stereochemically defined chiral building block for preparing D-peptides, D-amino acid-containing analogs, and downstream biochemical research intermediates.
1. D-Peptide Synthesis
D-Asparagine monohydrate supports peptide synthesis workflows where incorporation of D-amino acids is required for stability and stereochemical control. The α-amino group and carboxyl functionality can be transformed into N-protected and C-activated forms, while the side-chain primary amide can be retained or selectively protected to manage chemoselectivity during coupling and deprotection sequences. The D stereocenter enables construction of D-peptide segments and mixed stereochemistry scaffolds used in peptide chemistry and peptidomimetic design. The resulting D-Asn-containing peptides can serve as well-defined substrates for studying stereochemistry-dependent binding, proteolysis resistance, and conformational effects in synthetic and biochemical investigations.
2. Side-Chain Amide Derivatization
D-Asparagine monohydrate is suitable for amino acid derivatization strategies that exploit the side-chain primary amide to generate functionalized aspartamide motifs. The -CONH2 group can undergo controlled transformations such as acylation, activation for further coupling, or conversion to related carbonyl-bearing derivatives that preserve the D-configuration at the α-carbon. Protecting-group strategies can be applied to the α-amino and carboxyl functions to allow selective manipulation of the side-chain amide during multi-step synthesis. Downstream products derived from the side-chain functionalization can be used to access asparagine-based linkers, constrained analogs, and chemical handles for scaffold diversification in research-grade peptide and small-molecule synthesis.
3. Chemical Biology Probes
D-Asparagine monohydrate can be employed in chemical biology research where stereodefined amino acid building blocks enable controlled labeling and biomolecular interaction studies. The side-chain amide and the chiral α-center support incorporation into peptide probes and protein engineering constructs that require D-amino acid placement to tune recognition and protease stability. N- and C-terminal modification of D-Asn residues can be used to position functional groups for conjugation or to create defined binding epitopes for assay development. The hydrate form can be handled as a consistent starting material for preparing D-Asn-containing intermediates that feed into probe synthesis, molecular recognition studies, and stereochemical mapping of biomolecular interfaces.
4. Protein Engineering Substitutions
D-Asparagine monohydrate serves as a chiral amino acid precursor for protein engineering and synthetic biology applications that require D-amino acid substitutions within peptide or protein-like constructs. The α-amino acid framework can be protected and activated for incorporation into longer sequences, while the side-chain amide can participate in hydrogen-bonding networks that influence local structure and interaction patterns. The D stereochemistry enables systematic evaluation of stereochemical effects on folding, binding, and enzymatic processing using defined D-Asn-containing variants. Constructed D-peptide or D-amino acid-enriched segments can be used as mechanistic tools and model systems for studying how stereochemistry and side-chain functionality affect biomolecular behavior.
5. Pharmaceutical Intermediate Preparation
D-Asparagine monohydrate can be applied in pharmaceutical intermediate preparation where D-amino acid building blocks are used to construct stereochemically defined peptidomimetics and amide-rich scaffolds. The molecule's amino acid functionality supports conversion into protected derivatives compatible with peptide coupling chemistry and downstream functional group interconversions. Side-chain amide handling can be integrated into manufacturing-relevant protecting-group strategies to ensure chemoselective transformations during synthesis of D-Asn-containing intermediates. D-Asn-derived fragments can then be routed into larger synthetic sequences for fine chemical production, enabling consistent stereochemical incorporation into complex, amide-functional molecules used in applied chemical development programs.
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