L-Asparagine monohydrate is the naturally occurring, proteinogenic amino acid asparagine in its free-base form with an additional water molecule of crystallization, featuring an α-amino and α-carboxyl group on the backbone and a side chain bearing a primary amide (-CH2-CONH2). The molecule is specified as the L stereoisomer and contains the amide functionality that can participate in hydrogen bonding while remaining chemically distinct from carboxylic acid side chains, with the amino and carboxyl groups present as functional handles for salt formation and peptide coupling. As a free amino acid monohydrate, it is used as a substrate or building block in peptide synthesis workflows and in biochemical or analytical studies that require asparagine-containing structures, including preparation of peptide standards and characterization of amide-bearing amino acid residues.
CAT No: CP00303
CAS No:5794-13-8
Synonyms/Alias:Z-Cys(Z)-OH;57912-35-3;N,S-Di-Z-L-cysteine;N,S-Dicarbobenzoxy-L-Cysteine;N,S-diCBZ-cysteine;L-Cysteine,N,S-bis[(phenylmethoxy)carbonyl]-;AC1ODWAS;96070_ALDRICH;SCHEMBL1158249;96070_FLUKA;CTK5A7628;MolPort-003-939-921;PXKPRICKEUGRRR-INIZCTEOSA-N;ZINC2575491;7869AH;CZ-105;KM0153;AKOS024464823;AK163591;RT-003726;FT-0696166;ST24050361;N-(Phenylmethoxycarbonyl)-S-(phenylmethyloxycarbonyl)-L-cysteine;(2R)-2-(phenylmethoxycarbonylamino)-3-phenylmethoxycarbonylsulfanylpropanoicacid
L-Asparagine monohydrate is the amide-bearing, primary amino acid derived from L-aspartic acid, present here as the monohydrate salt form. The molecule contains a stereogenic center at the α-carbon with the L-configuration, a side-chain primary amide that participates in hydrogen bonding and can be chemically transformed into other functional groups, and a carboxamide/amine reactivity pattern compatible with standard amino acid coupling chemistries. The amino and carboxyl functionalities enable formation of peptide bonds after appropriate N- and C-terminal protection strategies, while the amide side chain can remain intact or be selectively modified depending on the protecting-group scheme. The hydrate form influences handling and crystallization behavior in manufacturing and analytical workflows, making it a practical amino acid input for peptide building block preparation and downstream derivatization routes.
1. Peptide Synthesis
L-Asparagine monohydrate is utilized in peptide synthesis workflows where the L-asparagine residue serves as a hydrogen-bonding side-chain component in linear peptides and peptide fragments. The α-amino and α-carboxyl groups can be converted into N-protected and C-activated forms for coupling, while the side-chain primary amide is compatible with many orthogonal protection strategies that preserve it during chain assembly. The stereochemical integrity of the L-configuration supports stereodefined peptide construction using standard peptide coupling chemistry, enabling incorporation into research-grade peptide libraries and sequence-defined constructs. Downstream, the intact side-chain amide can be retained for biochemical assays or converted into alternative side-chain functionalities for peptidomimetic design.
2. Chemical Biology Probes
L-Asparagine monohydrate is applied in chemical biology research to generate asparagine-containing peptide scaffolds and conjugation-ready intermediates that rely on amide-side-chain hydrogen bonding for molecular recognition. The side-chain primary amide can be engineered through controlled derivatization to introduce handles for labeling, affinity capture, or crosslinking while the α-amino acid backbone supports attachment to carrier proteins or biomolecular targets. The compound's defined stereochemistry and functional-group pattern make it suitable for constructing sequence motifs used in protein interaction studies, substrate analog generation, and binding-site mapping. Resulting derivatives can be used to probe biological pathways at the level of peptide recognition and biomolecular assembly without altering the core α-amino acid framework.
3. Protein Engineering Substrates
L-Asparagine monohydrate is relevant to protein engineering and enzyme studies where asparagine residues are incorporated into recombinant expression constructs or used to prepare synthetic substrates and segmental protein fragments. The L-asparagine backbone provides a stable α-amino acid motif, and the side-chain amide can participate in enzyme active-site interactions or serve as a structural element in designed protein variants. Protecting-group strategies that temporarily mask the α-amino and carboxyl groups enable preparation of peptide segments that can be ligated or assembled into larger biomolecular constructs. Downstream use includes generating defined peptide substrates for mechanistic studies, producing sequence-specific standards for characterization, and supporting structure-function investigations of asparagine-dependent recognition.
4. Amino Acid Derivatization
L-Asparagine monohydrate is used as a starting material for amino acid derivatization and side-chain functionalization schemes that convert the primary amide into alternative reactive groups. The side-chain amide can be transformed into carboxylic acid, heterocycle precursors, or other functional moieties under protecting-group controlled conditions, while the α-amino acid functionality supports selective N-protection and activation for subsequent coupling steps. The hydrate form can be advantageous for reproducible weighing and consistent feed composition in process chemistry intermediate preparation. Resulting derivatives serve as intermediates for fine chemical synthesis, peptide analog construction, and chiral building block development where the L-asparagine stereocenter is retained.
5. Pharmaceutical Manufacturing Intermediates
L-Asparagine monohydrate is incorporated into pharmaceutical manufacturing supply chains as a defined amino acid feedstock for producing peptide-based intermediates and asparagine-containing components used in process development. The presence of both amino and carboxyl functionalities enables conversion into protected forms and activated derivatives that can be used in controlled peptide coupling steps during manufacturing of peptide intermediates. Side-chain amide stability under appropriate protection conditions supports scalable synthesis of sequence-defined building blocks, while controlled deprotection strategies allow downstream generation of free functional groups for further processing. The compound's manufacturability as a hydrate supports practical handling for specialty chemical production and industrial intermediate preparation where reproducible solid-state behavior and consistent composition are required.
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