Asparaginamide - ≥95% , CAS No.16748-73-5

CAS: 16748-73-5 Cat. No.: A1071142 Summenformel: C₄H₉N₃O₂ Molekulargewicht: 131.13

GRADE & PURITY ≥95%

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Protected from light,Store at -20°C,Argon charged

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

C(C(C(=O)N)N)C(=O)N

IUPAC Name

(2S)-2-aminobutanediamide

InChIKey

DSLBDPPHINVUID-REOHCLBHSA-N

INCHI

1S/C4H9N3O2/c5-2(4(7)9)1-3(6)8/h2H,1,5H2,(H2,6,8)(H2,7,9)/t2-/m0/s1

Isomere SMILES

C([C@@H](C(=O)N)N)C(=O)N

Alternative CAS-Nummer

16748-73-5,158606-68-9

Molekulargewicht

131.13

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Klasse Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Ebene5 Amino acids and derivatives
          • Ebene6 Alpha amino acids and derivatives
            • Ebene7 Asparagine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Klasse: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Asparagine and derivatives
• Alternative Parents: Alpha amino acid amides Fatty amides Primary carboxylic acid amides Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Asparagine or derivatives - Alpha-amino acid amide - Fatty amide - Fatty acyl - Carboxamide group - Primary carboxylic acid amide - Organopnictogen compound - Organic nitrogen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Organic oxygen compound - Carbonyl group - Amine - Hydrocarbon derivative - Organic oxide - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as asparagine and derivatives. These are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Molekulargewicht: 131.130 g/mol
• XLogP3: -1.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 131.069 Da
• Monoisotopic Mass: 131.069 Da
• Topological Polar Surface Area: 112.000 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 134.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No application protocols are specified for this item. As a small-molecule building block, procedures will depend on the intended chemistry (e.g., amide coupling, conjugation, stability studies).

General starting points (literature, to be tailored by the user):

• Stock solutions: Prepare 100–500 mM in water, DMF, or DMSO; sterile-filter aqueous stocks (0.22 μm) for biochemical assays. Record exact solvent and concentration for reproducibility.
• Conjugation: For NHS-ester labeling, use pH 7.5–8.5 buffers, keep reaction times short (≤2 h), and quench residual ester with Tris or ethanolamine.
• Stability studies: For deamidation modeling, incubate in buffered solutions across pH 6–9 at controlled temperature; analyze by LC-MS for succinimide/imide formation.

Please consult the primary literature and adjust conditions to your substrates and instrumentation. For validated, item-specific protocols, refer to the forthcoming CoA/Spec Sheet if provided.

Biological Roles

Biochemically, Asparaginamide is closely related to the side-chain chemistry of asparagine and the deamidation processes that convert asparagine residues to aspartate or isoaspartate in proteins (literature).

• Deamidation pathway models: Asparaginamide-containing small molecules can form succinimide intermediates under physiological to mildly basic conditions, paralleling protein deamidation. Studying these small-molecule analogs helps dissect kinetics, isotope effects, and the influence of neighboring groups.
• Hydrogen-bonding and recognition: With multiple H-bond donors/acceptors, asparaginamide motifs participate in tight binding and molecular recognition in aqueous environments—useful in ligand design and probing enzyme active-site preferences (e.g., amidases/peptidases).
• Metabolic relevance: Although not a canonical metabolite, the diamide framework models features of peptide backbones and asparagine side chains, allowing evaluation of amidase activity, protease susceptibility, and transport via peptide-like carriers in in vitro systems.
• Stability considerations: The absence of a carboxylate changes ionization and transport properties relative to asparagine; the free primary amine can be protonated near neutral pH, influencing uptake and enzyme interactions in biochemical assays.

Note: All statements above reflect general biochemical context and literature; this product is supplied strictly for research use only and is not intended for diagnostic, therapeutic, or dietary applications.

Buffer Applications

Asparaginamide is not a standard biological buffer component. It lacks the defined pKa spacing and buffering capacity typical of purpose-built zwitterionic buffers (e.g., HEPES, MOPS) or amino acid buffers (e.g., glycine).

• Typical usage: May be included in assay media as a substrate/ligand analog or to modulate polarity/ionic strength, but not as a primary buffer.
• Recommendation: For buffering near neutral pH, use Good’s buffers (HEPES, MOPS, PIPES) or phosphate. If Asparaginamide must be present, prepare the buffer separately, then dissolve Asparaginamide into the pre-set buffer to avoid unintended pH drift.
• Practical tip: Verify final pH after adding Asparaginamide—its primary amine can sequester protons and slightly alter pH in low-capacity systems.

For detailed recipes and pH-temperature profiles, consult standard buffer preparation references; no item-specific buffer parameters are provided for this product.

Green Alternatives

While Asparaginamide itself is a substrate/building block, greener choices relate to the reaction media and coupling systems used with it.

Greener solvent/coupling considerations (literature):

• Substitute DMF/NMP with 2-MeTHF, CPME, ethyl acetate, or water/ethanol where feasible; ensure solubility and reaction rates are acceptable.
• Favor OxymaPure/EDC or CDI in greener solvents over HOBt/HATU where safety or waste minimization is a priority. Avoid explosive benzotriazoles.
• Aqueous micellar media (e.g., TPGS-750-M) can enable acylations at ambient temperature with reduced solvent volumes.

Comparison snapshot (literature):

• DMF: excellent solubility and coupling efficiency; toxic/reprotoxic; challenging waste handling.
• 2-MeTHF: bio-based, lower toxicity, easier workup; may require co-solvent for dissolution and careful water control.
• Water/EtOH: benign, minimal VOC impact; limited for moisture-sensitive activations; hydrolysis competes with coupling.

Process tips:

• Assess solubility of both partners in greener media; seed with small DMF/DMSO fractions only if essential.
• Use in situ activation methods that minimize stoichiometric byproducts (e.g., enzymatic ligation or EDC with catalytic NHS/Oxyma).
• Optimize pH to balance amine nucleophilicity and minimize amide hydrolysis; buffer capacity is crucial in aqueous systems.

Pharmaceutical Uses

No pharmacopeial listing or excipient role is specified for this item; refer to CoA/Spec Sheet.

General formulation context (literature, non-clinical):

• As a polar, multifunctional small molecule, Asparaginamide may be explored as a peptide-mimetic building block or as a ligand in formulation screening studies (e.g., salt/solid-form screens) but is not a standard pharmaceutical excipient.
• Potential roles in research settings include:
  • Conjugation handle via the primary amine to generate pro-matrices or test conjugates.
  • Model compound for evaluating deamidation liabilities in peptide formulations under stress (pH, temperature, excipients).
• Compatibility: Typically compatible with aqueous systems; verify interaction with common excipients (polysorbates, sugars, amino acids) experimentally.

Compliance note: This product is supplied for research use only. It is not approved for human or veterinary use, nor for incorporation into commercial drug products without appropriate qualification and regulatory review.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature estimate (C4H9N3O2): ~131.13 g/mol.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: C4H9N3O2 for asparaginamide.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: diamide amino acid derivatives often show high mp with potential decomposition; verify experimentally.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: typically highly soluble in water and polar protic/aprotic solvents (e.g., water, methanol, DMF); limited solubility in nonpolar media.
• pKa: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: primary amine pKa (conjugate acid) commonly in the 8–10 range; amide groups are non-basic/very weakly basic; check actual value.
• logP: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature expectation: strongly negative (very hydrophilic) due to three hydrogen-bond donors and two carbonyl acceptors.
• Density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Notes:

• As a solid building block, polymorphism and hydration state can influence melting behavior and measured solubility; verify with the supplied batch documentation and perform small-scale solubility trials if critical.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret grades (general guidance):

• Research/Biochemical grade: Emphasizes low residual inorganic content and low bioburden; suitable for biochemical assays and synthesis. Typical controls include identity (NMR/HRMS), purity (HPLC), and water content (KF). Verify which metrics are provided for this SKU in the CoA.
• Peptide-synthesis suitability: For amine-bearing building blocks, residual water and inorganic salts can hamper coupling; high assay purity and clear residual solvent limits are beneficial. Low UV background is helpful if monitoring couplings by HPLC at 214–220 nm.
• Stabilizers: None indicated. If the product includes any stabilizers or salt forms, these will be explicitly stated on the label/CoA. Absence of a note generally indicates neat free base/neutral form.

Batch-specific documentation:

• Identity confirmation (e.g., 1H/13C NMR, MS), purity (HPLC/UPLC), water content (KF), and residual solvents are batch-dependent. For critical applications (e.g., solid-phase coupling), request and review the CoA and, if needed, a detailed specification sheet prior to use.

Reaction and Applications

Asparaginamide serves as a versatile, hydrophilic building block for peptide-mimetic synthesis and for probing asparagine/aspartate deamidation pathways (literature).

Key application areas (literature):

• Amide bond formation: The α-amine can be acylated with activated carboxylic acids (acid chlorides, anhydrides, or via EDC/HATU/HBTU) to afford N-acyl derivatives and pseudopeptide linkages.
• Protecting-group chemistry: Temporary protection of the α-amine (e.g., Boc, Fmoc, Cbz) enables selective modification of either terminal amide (e.g., activation to imidate/imidoyl species under forcing conditions) or side-chain elaboration.
• Deamidation models: Under mildly basic or dehydrating conditions, asparaginamide motifs can cyclize to a succinimide intermediate, mirroring known protein deamidation pathways; this is useful for mechanistic and stability studies.
• Conjugation handles: The primary amine allows attachment to reporters, resins, or linkers via NHS-esters or isothiocyanates; polar character improves aqueous compatibility.
• Heterocycle formation: Dehydrative cyclizations can afford imide derivatives; careful control avoids over-dehydration or rearrangement.

Practical tips:

• Use anhydrous solvents (DMF/NMP) and base (DIPEA) for clean amide couplings; add HOAt/HOBt or Oxyma to suppress side reactions.
• Maintain moderate temperatures (0–25 °C) during activation to limit cyclization to succinimide; quench promptly after coupling.
• For aqueous bioconjugations, NHS-esters react efficiently with the α-amine near pH 7.5–8.5; minimize exposure time to reduce hydrolysis.

Reaction Conditions

General, literature-based guidance for common transformations involving Asparaginamide:

• Amide coupling at the α-amine:
  • Solvent: Anhydrous DMF, NMP, or DCM/DMF (1:1).
  • Reagents: EDC·HCl (1.1–1.5 eq) + Oxyma/HOAt (1.1–1.5 eq), or HATU/HBTU (1.1–1.3 eq); base DIPEA (2–4 eq).
  • Temperature: 0–25 °C.
  • Time: 0.5–4 h, monitor by TLC/HPLC.
  • Notes: Keep cold during activation; add amine last to limit background hydrolysis.
• N-Protecting group installation (Boc, Fmoc):
  • Boc2O (1.2–1.5 eq), DIPEA (2–3 eq), dioxane/water or MeCN, 0–25 °C; 1–2 h.
  • Fmoc-Cl (1.2–1.5 eq), Na2CO3 (aq), dioxane/water; 0–25 °C; 1–2 h.
  • Quench and extract under mildly basic conditions to avoid premature deprotection.
• NHS-ester conjugation (aqueous):
  • Buffer: 50–100 mM phosphate or bicarbonate, pH 7.5–8.5.
  • Conditions: 0.5–2 h at RT; limit DMSO to 10–20% v/v to maintain solubility; protect from moisture for neat NHS-esters.
  • Tip: Use ≥5-fold molar excess of NHS-ester when labeling in dilute aqueous setups.
• Avoid: Strong dehydrating agents (POCl3, SOCl2) or high heat/base that promote cyclization to succinimides unless this outcome is intended.

All values above reflect general literature practice and should be optimized for the specific substrate set and scale.

Safety and Handling

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.

General safety guidance (for research/lab use only):

• PPE: Wear lab coat, safety glasses, and suitable gloves (e.g., nitrile). Avoid inhalation of dust and contact with skin/eyes.
• Handling: Solid, hydrophilic diamide/amine; minimize dust generation. Use in a fume hood during weighing and transfers.
• Incompatibilities: Strong oxidizing agents and strong dehydrating/condensing reagents may induce side reactions (e.g., cyclodehydration to succinimide-like byproducts). Avoid mixing with isocyanates or acid chlorides without controlled conditions.
• First aid overview:
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; obtain medical help.
• Fire safety: Likely combustible organic solid; use water spray, dry chemical, CO2, or foam as appropriate. Combustion may yield nitrogen oxides and CO/CO2.
• Spills: Avoid dust; sweep up carefully and dispose of according to institutional and local regulations.
• SDS: For authoritative hazard classifications, exposure limits, and disposal details, consult the product-specific SDS.

Solvent Selection

This product is a polar, highly hydrogen-bonding solid building block rather than a solvent. Solvent selection pertains to its dissolution and reaction media.

• Polarity/miscibility (literature expectations):
  • Readily soluble in water and highly polar organic solvents (e.g., methanol, ethanol, DMF, DMSO).
  • Poorly soluble in nonpolar solvents (e.g., hexanes, toluene) absent ion-pairing or co-solvents.
• Practical dissolution tips:
  • For analytical prep: Dissolve in water or aqueous buffer, or use DMSO/DMF stock followed by dilution. Gentle warming (≤40 °C) and sonication can assist dissolution.
  • For coupling chemistry: Anhydrous DMF, NMP, or DCM/DMF mixtures are commonly used; add base (e.g., DIPEA) as required by the coupling system.
• When to choose aqueous vs. organic media:
  • Aqueous media for biochemical assays, stability/deamidation studies, and crystallization screens.
  • Anhydrous polar aprotics for acylation, carbodiimide/uronium couplings, or protecting-group chemistry.
• Comparison (literature-based): • Water: green, excellent solubility, but limited for moisture-sensitive couplings.
  • DMF/DMSO: strong solvating power for amides/amines; facilitate coupling; mind removal and toxicity profile.
  • Alcohols (MeOH/EtOH): intermediate option; may participate in side esterification under strong activation—control conditions.

Storage and Reconstitution

• Storage Conditions (from Product Data): Room temperature.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Best practices:

• Keep container tightly closed in a dry, well-ventilated place. Hygroscopic uptake can alter mass and concentration accuracy; consider desiccation for long-term storage.
• Protect from strong light and reactive vapors (acyl chlorides, strong acids/bases) that could induce side reactions.
• Reconstitution:
  • For biochemical use: Prepare aqueous stocks (e.g., 100–500 mM), adjust pH if necessary, and filter-sterilize (0.22 μm). Store aliquots at 2–8 °C or −20 °C to minimize microbial growth; avoid repeated freeze–thaw.
  • For synthetic use: Dissolve in anhydrous DMF/DMSO immediately before use; purge headspace with inert gas if storing solutions >24 h.
• Shelf life: Batch-dependent; monitor by HPLC or NMR for signs of degradation (e.g., cyclization/deamidation products) if stored in solution.

Always refer to the product label and CoA/SDS for the most accurate, lot-specific handling instructions.

Structure and Identity

Asparaginamide is the diamide derivative of aspartic acid (formally, the carboxyl group of L-asparagine converted to an amide), yielding a neutral, highly polar amino acid derivative.

• SKU: A1071142
• Product Name: Asparaginamide
• CAS: 16748-73-5 (literature)
• PubChem CID: 447212 (literature)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: O=C(N)C(N)CC(=O)N (literature)
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Note: Literature suggests C4H9N3O2 for the neutral diamide form.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Note: Literature formula C4H9N3O2 corresponds to ~131.13 g/mol.

Structural features (general description):

• Contains two primary amide groups (terminal –CONH2 at both the α- and β-termini) and one α-primary amine (–CH(NH2)–).
• Acyclic four-carbon backbone analogous to aspartic acid/asparagine; no rings or stereocenters specified in the item listing.
  • Note: The parent amino acid (asparagine) typically has an L-stereocenter at the α-carbon. If stereochemistry is critical, confirm with the specific lot CoA.
• 2D structure in words: An α-carbon bearing an amino substituent (NH2), flanked on one side by a terminal amide carbonyl (–CONH2) and on the other by a methylene (–CH2–) that terminates in a second amide carbonyl (–CONH2).

Synthetic Utility

Functional handles and reactivity (literature):

• Nucleophilic α-amine: Amenable to acylation (acid chlorides/anhydrides), carbodiimide-mediated couplings (EDC/DIPEA, DIC/DMAP), and uronium salts (HATU/HBTU/Oxyma). Enables synthesis of N-acyl derivatives, peptidomimetics, and linkers.
• Dual amide termini: While typically inert to mild bases/nucleophiles, they can participate in dehydration/activation chemistry to form imidoyl or imide species under forcing conditions, granting access to heterocycles or succinimide analogs.
• Protecting groups: The α-amine can be protected as Boc, Fmoc, or Cbz; orthogonal strategies allow stepwise functionalization. Protection suppresses undesired cyclization during side-chain manipulations.
• Retrosynthetic value: Serves as a convergent node to introduce “asparagine-like” side chains without free acid functionality—useful where neutral, highly polar residues are desired (e.g., in fragment libraries or solubility enhancers).
• Conjugation chemistry: NHS-esters, isothiocyanates, or activated carbonates efficiently label the primary amine, allowing incorporation into probes and affinity matrices.

Select cautions:

• Avoid strong dehydrating conditions or prolonged base at elevated temperatures to minimize intramolecular cyclization to succinimide intermediates.
• Balance activation strength with chemoselectivity; Oxyma-based systems reduce racemization and side reactions compared with neat carbodiimides.

Target Specificity

Not applicable. This product is a small-molecule building block, not an antibody, enzyme, or affinity reagent. No antigen/epitope specificity, clone, or isotype information applies.