DL-Serine hydrazide - ≥98% , CAS No.64616-76-8

CAS: 64616-76-8 Cat. No.: D1073686 Summenformel: C₃H₉N₃O₂ Molekulargewicht: 119.120 EG-Nummer: 613-642-7

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥98%

Storage

Room temperature

Reinheit

≥98%

Namen und Kennungen

Kanonisches Lächeln

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

IUPAC Name

2-amino-3-hydroxypropanehydrazide

InChIKey

YTHVXUGXVASXJZ-UHFFFAOYSA-N

INCHI

1S/C3H9N3O2/c4-2(1-7)3(8)6-5/h2,7H,1,4-5H2,(H,6,8)

Molekulargewicht

119.120

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 Serine 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: Serine and derivatives
• Alternative Parents: Carboxylic acid hydrazides Primary alcohols Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Serine or derivatives - Carboxylic acid hydrazide - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Primary amine - Primary alcohol - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Carbonyl group - Amine - Alcohol - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as serine and derivatives. These are compounds containing serine or a derivative thereof resulting from reaction of serine 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: 119.120 g/mol
• XLogP3: -2.800
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 119.069 Da
• Monoisotopic Mass: 119.069 Da
• Topological Polar Surface Area: 101.000 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 84.600
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 tested bioassay protocols are provided for this item. For general use, consult standard procedures for:

• Hydrazone bioconjugation: Periodate oxidation of glycans (if needed), reaction in acetate buffer (pH ~5.5) with aniline catalysis, optional reductive stabilization.
• Amide coupling: EDC/Oxyma or HATU protocols in DMF/NMP with DIPEA, monitoring by LC–MS.

These are literature guidelines; adapt to your system and consult primary references. Item‑specific protocols are not provided; refer to CoA/Spec Sheet and SDS.

Biological Roles

No direct biological role is assigned to DL‑serine hydrazide; it is a synthetic derivative intended for research use. The notes below refer to the parent amino acid serine (literature/general context) and to hydrazide chemistry in bioconjugation.

• Parent amino acid (serine): Serine is a proteinogenic amino acid involved in metabolic pathways such as one‑carbon metabolism (via serine hydroxymethyltransferase) and is common at enzyme active sites due to the nucleophilic Ser–OH.
• Hydrazide functionality in bioconjugation: Hydrazides react with aldehydes/ketones on biomolecules (e.g., periodate‑oxidized glycans) to form hydrazones, enabling labeling or immobilization. DL‑serine hydrazide provides a minimal hydrazide motif plus an α‑amine and β‑OH that can be further derivatized or serve as model substrates.
• Stereochemical note: As a DL mixture, it lacks defined chirality for biological recognition and is not suited for chirality‑dependent biochemical studies without resolution.

Important: The above is general literature information. This product is supplied strictly for research use; it is not intended for diagnostic or therapeutic applications.

Buffer Applications

DL‑Serine hydrazide is not a conventional buffering agent. It lacks a well‑defined, narrow pKa pair suitable for high‑capacity buffering in common biological pH ranges.

Practical lab note (literature/general):

• For hydrazone ligations to aldehydes/ketones, use acetate (pH 5–6) or phosphate (pH 6–7.4) buffers. Catalytic aniline can accelerate reactions under these conditions.
• For amide couplings, non‑buffered organic media (DMF, DMSO) or mixed aqueous/organic systems are typical; buffering is determined by the coupling chemistry rather than by the reagent itself.

Green Alternatives

As a polar, multifunctional building block, DL‑serine hydrazide is often used in amide coupling and hydrazone ligations. Greener practice focuses on solvent choice, coupling reagents, and catalysts. The following comparisons are general/literature guidance.

Greener choices and trade‑offs:

• Solvents
  • Prefer water, aqueous buffers, or ethanol for hydrazone ligations when feasible. These reduce reliance on DMF/DMSO but may require catalysts (e.g., aniline) for rate enhancement.
  • For peptide couplings, ethyl acetate, 2‑MeTHF, or CPME as workup/extraction solvents can lower environmental impact versus dichloromethane.
• Coupling reagents
  • Oxyma/EDC systems can be less hazardous than HOBt‑based protocols (reduced explosivity). Consider DMTMM in water for certain amide formations, minimizing dipolar aprotic solvents.
  • Avoid excessive carbodiimide use; stoichiometric coupling agents generate urea waste—optimize equivalents and consider recycling protocols where available.
• Catalysts for hydrazone formation
  • Aniline catalysis enables near‑neutral aqueous conditions, reducing solvent hazards; catalytic loadings (5–20 mM) limit mass intensity. Explore benign catalysts (e.g., sulfoanilines) for fully aqueous systems.
• Energy and protection strategies
  • Run at ambient temperature where possible; minimize protection/deprotection cycles on the serine OH and α‑amine to reduce steps, reagents, and solvent consumption.

Example comparison (general):

• Traditional: Hydrazone in DMF with acetic acid (anhydrous).
• Greener: Hydrazone in acetate buffer (pH 5.5) with 10 mM aniline, room temperature, followed by aqueous workup and ethanol precipitation.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item. DL‑Serine hydrazide is offered for research and laboratory use only.

General formulation/processing context (literature/general):

• Linker chemistry: Hydrazides are used in process development for conjugating APIs or intermediates to aldehyde‑bearing carriers (e.g., solid supports) via hydrazone formation, with optional reduction to stabilize the linkage.
• Intermediate for rearrangements: As an acyl hydrazide, it can serve as a precursor to acyl azides for Curtius rearrangements in synthetic routes to amines/carbamates during API intermediate development.

No clinical or therapeutic claims are made or implied.

Physical Properties

Item-specific specifications are not provided in the Product Data. The following are literature/computed values and general expectations for serine hydrazide; they are NOT item specifications.

• Molecular formula (literature/computed): C3H9N3O2
• Molecular weight (literature/computed): ~119.12 g/mol
• Physical state/appearance: Not specified for this item; refer to CoA/Spec Sheet. (Hydrazide amino acids are typically white to off‑white solids; literature/general.)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable (decomposes before boiling; literature/general for peptide hydrazides).
• pKa values (literature, approximate): α‑NH3+ ~9–10; hydrazide –NH–/–NH2 typically acidic/basic sites with conjugate pKa’s in the ~2–4 (amide) and ~4–6 (hydrazide NH) ranges; exact values for DL‑serine hydrazide not established here.
• LogP (cLogP, literature expectation): Strongly negative (highly polar); exact value not specified.
• Solubility (literature expectation): High in water and polar protic solvents (e.g., water, methanol); enhanced in aqueous buffers near neutral to slightly acidic/basic pH. Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index, density, UV cutoff, residual metals, water/peroxide content: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• In the absence of a stated grade, users should verify suitability for purpose (e.g., peptide synthesis, conjugation chemistry) using the Certificate of Analysis (CoA) for assay/purity, residual solvents, and chromatographic profile.

General guidance on grades (context, not item‑specific):

• Research/bioconjugation grade: Prioritizes low inorganic/organic impurities, minimal residual metals, and defined water content—important for coupling efficiency and reproducibility.
• Peptide synthesis grade: Low UV‑active impurities and low water are critical to avoid side reactions during activation (e.g., EDC/HOBt, HATU) and to ensure clean LC–MS profiles.
• Stabilizers: Hydrazide salts or added bases are typically avoided; if present, they should be disclosed on the CoA as they can affect coupling stoichiometry.

What to check on receipt:

• Assay (% area by HPLC), identity (HRMS/NMR), water (KF), and residual inorganic salts. For solid amino acid derivatives, a sharp melting/decomposition range and a single major HPLC peak are typical acceptance criteria (project‑dependent).

Reaction and Applications

DL-Serine hydrazide is a versatile bifunctional building block combining an α‑amine, a β‑alcohol, and an acyl hydrazide. This constellation of groups enables several useful transformations in synthesis and bioconjugation (literature/general guidance below; not item‑specific):

• Hydrazone/oxime ligations: The terminal hydrazide (–CONH–NH2) condenses with aldehydes/ketones to form hydrazones, typically at pH 5–6. Rates can be enhanced with aniline or p‑phenylenediamine catalysts. Resulting hydrazones can be reduced (e.g., NaBH3CN) to more stable hydrazide/amine linkages.
• Precursor to acyl azides and thence amines/urethanes (Curtius): Acyl hydrazides can be nitrosylated (NaNO2, mineral acid, 0–5 °C) to give acyl azides, enabling Curtius rearrangements to isocyanates and subsequent trapping (e.g., with alcohols to carbamates or amines after hydrolysis). For α‑amino acyl systems, protect or control the α‑amine to avoid side reactions.
• Peptide chemistry (hydrazide method): Carboxy‑terminal hydrazides are widely used as precursors to peptide thioesters via in situ activation (e.g., NaNO2 activation followed by thiol capture) to support native chemical ligation (NCL). Serine hydrazide analogs can serve as minimal models for optimizing these workflows.
• Amide bond formation: The α‑amine can be coupled to carboxylic acids (standard coupling reagents: EDC/HOBt, HATU, PyBOP, DIC/Oxyma). Conversely, the hydrazide can be acylated by activated carboxylic acids to furnish diacyl hydrazides.
• Selective derivatization at the β‑OH: The serine side‑chain hydroxyl allows orthogonal protection (e.g., TBDMS, benzyl) or transformation (e.g., Mitsunobu to introduce other functionalities), while preserving hydrazide reactivity.

Practical tips:

• Control pH carefully during hydrazone formation; mildly acidic conditions favor kinetics without excessive α‑amine protonation losses in nucleophilicity.
• For nitrosylations/azide formation, maintain low temperature, exclude excess water, and quench safely; acyl azides can be energetic—scale appropriately.

Reaction Conditions

Representative literature conditions for transformations involving amino acid hydrazides (guidance only; optimize per substrate). These are NOT item specifications.

• Hydrazone formation (bioconjugation):
  • Substrates: Aldehyde‑bearing biomolecule + DL‑serine hydrazide.
  • Solvent: 50–100 mM acetate buffer, pH 5.0–5.5; optional 5–20 mM aniline as catalyst.
  • Temperature/time: 20–25 °C; 1–4 h (fast aldehydes) to overnight (hindered ketones).
  • Workup: Desalting or dialysis; optional reduction with NaBH3CN or pyridine‑borane to stabilize.
• Acyl azide formation (from hydrazide):
  • Reagents: NaNO2 (1.1–1.5 equiv) in cold aqueous acid (e.g., 1–2 M HCl), 0–5 °C.
  • Procedure: Add NaNO2 to a cold solution of the hydrazide; maintain low temperature; extract or directly thermally rearrange to isocyanate under anhydrous conditions; trap with ROH/RNH2.
  • Cautions: Acyl azides may be energetic; use small scale, shielding, and temperature control.
• Amide coupling via α‑amine:
  • Reagents: HATU or EDC·HCl/Oxyma (1.1–1.5 equiv), base (DIPEA, 2–4 equiv).
  • Solvent: Dry DMF or NMP; 0.05–0.2 M.
  • Temperature/time: 0–25 °C; 1–16 h.
  • Notes: Protect hydrazide if competing acylation is problematic; employ selective protection or adjust stoichiometry.
• Protection of functional groups:
  • α‑Amine: Boc2O, DIPEA, DMF, 0–25 °C.
  • β‑OH: TBDMS‑Cl, imidazole, DMF; or benzylation under mild conditions.

Always monitor by LC–MS/HPLC and confirm identity/purity before scale‑up.

Safety and Handling

No GHS classification or hazard statements are provided in the Product Data for this item. The guidance below is general for small‑molecule hydrazides and amino acid derivatives; always consult the product‑specific SDS.

• GHS/Signal word/Pictograms: Not specified for this item; refer to SDS.
• Primary hazards (general for hydrazides): Irritation to skin, eyes, and respiratory tract; potential sensitization. Some hydrazides can decompose on heating and may form nitrogen‑containing gases. Avoid dust formation and inhalation.
• PPE: Laboratory coat, safety glasses or face shield, and appropriate chemical‑resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure when weighing or dissolving.
• Handling notes:
  • Keep containers tightly closed; protect from moisture—hydrazides and free amines can absorb CO2/H2O and form salts.
  • Avoid contact with strong oxidizers and strong acids/bases that could promote decomposition or side reactions (e.g., hydrazide acyl transfer).
• First aid (general):
  • 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 advice if irritation develops.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Nonvolatile solid; if involved in fire, use water spray, CO2, dry chemical, or foam. Thermal decomposition may produce nitrogen oxides; firefighters should wear SCBA.
• Waste: Collect aqueous and organic waste streams containing hydrazides in labeled, compatible containers. Dispose according to institutional and local regulations.

Solvent Selection

This product is a small, highly polar, multifunctional solid (α‑amine, hydrazide, and β‑alcohol). Solvent choice should support both dissolution and the intended reaction chemistry.

General/literature guidance (not item‑specific):

• Aqueous systems: Often freely soluble in water; buffers at pH 5–8 commonly used for hydrazone/oxime ligations to carbonyl partners. Slightly acidic pH (5–6) can accelerate hydrazone formation.
• Polar protic solvents: Methanol, ethanol—useful for stock solutions and as co‑solvents with water. Avoid excessive alcohol when performing carbodiimide couplings to minimize esterification.
• Polar aprotic solvents: DMF, DMSO—excellent for peptide coupling (EDC/HOBt, HATU, or PyBOP systems). Small amounts of base (DIPEA) can be added to neutralize the ammonium form of the α‑amine if needed.
• Less polar solvents: Poorly compatible due to high polarity; use only as minor co‑solvents if required.

Selection tips:

• For bioconjugation to aldehydes/ketones, favor aqueous acetate or phosphate buffers (pH 5–6) with aniline catalysts when speed is required.
• For peptide coupling/activation, dry DMF or NMP with standard coupling additives improves solubility and reaction rates.
• For Curtius/azide routes from hydrazides, mixed aqueous/organic media at low temperature are used during nitrosylation; maintain anhydrous aprotic conditions for subsequent steps.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Container: Tightly sealed, in a dry environment. Hydrazides and free amines can absorb moisture/CO2; a desiccator or moisture‑barrier packaging is recommended.
• Protection: Store away from strong oxidizers and acids/bases. Avoid prolonged exposure to light and heat.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution (general guidance, not item‑specific):
  • For aqueous use, dissolve in deionized water or appropriate buffer (e.g., 50–100 mM acetate or phosphate). Adjust pH to improve solubility if required.
  • For organic reactions, dissolve in dry DMF, DMSO, or ethanol. Filter sterile solutions through 0.22 μm if needed for bioconjugation.
  • Prepare fresh solutions for sensitive transformations (nitrosylation, hydrazone ligation) and store aliquots at 2–8 °C if short‑term reuse is anticipated.
• Stability: Without item‑specific data, assume best practice is cool, dry storage and minimize exposure to air and moisture. For definitive stability and shelf‑life, refer to the product’s CoA and SDS.
• Research use: For research use only (per Product Data).

Structure and Identity

DL-Serine hydrazide is the hydrazide of the α-amino acid serine, where the C‑terminal carboxyl group is converted to an acyl hydrazide (–CONHNH2) while retaining the α‑amine and β‑hydroxymethyl side chain.

• SKU: D1073686
• Product name: DL-Serine hydrazide
• CAS: 64616-76-8
• PubChem CID (catalog): 6453265 (catalog reference)
• InChIKey (catalog): 446389 (as provided; non-standard length)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula (literature/computed for serine hydrazide): C3H9N3O2
• Molecular weight (literature/computed): ~119.12 g/mol

Structural features (general/literature description):

• Functional groups: α‑primary amine (–NH2), acyl hydrazide at the C‑terminus (–CONHNH2), and β‑hydroxymethyl side chain (–CH2OH).
• Backbone: HO–CH2–CH(NH2)–CO–NH–NH2.
• Stereochemistry: “DL” denotes racemate; both L‑ and D‑enantiomers are present.
• 2D description: A three‑carbon chain where C1 bears hydroxyl (–CH2OH), C2 is α‑chiral with –NH2 and –H, and C3 is the carbonyl carbon of an amide extended to hydrazide (–CONH–NH2).

Synthetic Utility

Key reactivity elements and how they can be leveraged (literature/general guidance):

• Hydrazide (–CONHNH2):
  • Nucleophilic nitrogen enables formation of hydrazones with carbonyl compounds and acylation to give diacyl hydrazides.
  • Nitrosylation to acyl azides enables Curtius rearrangement to isocyanates, then amines/carbamates—useful for homologation or protecting‑group strategies.
• α‑Amine:
  • Readily coupled to carboxylic acids using EDC/Oxyma, HATU, or DMTMM. Protecting groups (e.g., Boc, Fmoc) can be employed to direct chemoselectivity when the hydrazide must remain unreacted.
• β‑Hydroxyl (serine side chain):
  • Orthogonal protection (e.g., TBDMS, benzyl) allows selective downstream transformations (e.g., Mitsunobu inversion/substitution, phosphorylation mimics) without perturbing hydrazide chemistry.
• Racemate (DL):
  • Suitable where chirality is unimportant (linker or handle installation). If enantiospecific outcomes are needed, resolve or start from enantiopure serine.

Retrosynthetic value:

• Acts as a compact, polar bifunctional synthon for introducing both nitrogen and oxygen functionality into targets, enabling late‑stage conjugation or diversification on carbohydrate, peptide, or polymer scaffolds.

Target Specificity

Not applicable. This product is a small organic building block, not an antibody, enzyme, or affinity reagent. No antigen/epitope or species specificity applies.