Ala-Phe - ≥98% , CAS No.3061-90-3

CAS: 3061-90-3 Cat. No.: A121378 Summenformel: C₁₂H₁₆N₂O₃ Molekulargewicht: 236.27

QUALITÄT & REINHEIT ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Spezifikationen

Spezifikationen & Reinheit

≥98%

Biochemische und physiologische Mechanismen

Alanyl dipeptides such as ala-leu, ala-lys, ala-gly, ala-pro, ala-tyr and ala-phe may be used in physicochemical studies or to evaluate dipeptide separation technologies. Alanyl dipeptides may also be used for studying cell uptake mechanisms, dipeptide me

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

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

Reinheit

≥98%

Namen und Kennungen

Pubchem Sid

488187022

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488187022

Kanonisches Lächeln

CC(C(=O)NC(CC1=CC=CC=C1)C(=O)O)N

IUPAC Name

(2S)-2-[[(2S)-2-aminopropanoyl]amino]-3-phenylpropanoic acid

InChIKey

OMNVYXHOSHNURL-WPRPVWTQSA-N

INCHI

1S/C12H16N2O3/c1-8(13)11(15)14-10(12(16)17)7-9-5-3-2-4-6-9/h2-6,8,10H,7,13H2,1H3,(H,14,15)(H,16,17)/t8-,10-/m0/s1

Isomere SMILES

C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)N

WGK Deutschland

3

Molekulargewicht

236.27

Reaxy-Rn

2943892

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2943892&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Klasse Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Klasse: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Not available
• Direct Parent: Peptides
• Alternative Parents: Phenylalanine and derivatives N-acyl-alpha amino acids Phenylpropanoic acids Amphetamines and derivatives Amino acids Propargyl-type 1,3-dipolar organic compounds Monocarboxylic acids and derivatives Carboxylic acids Carboximidic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alpha peptide - Phenylalanine or derivatives - N-acyl-alpha-amino acid - N-acyl-alpha amino acid or derivatives - 3-phenylpropanoic-acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - Monocyclic benzene moiety - Benzenoid - Amino acid or derivatives - Amino acid - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organopnictogen compound - Primary aliphatic amine - Organic oxygen compound - Amine - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organic oxide - Primary amine - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
• External Descriptors: dipeptide

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

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ACE Tclin Angiotensin-converting enzyme (1423 Activities)

Discover Target: ACE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MME Tclin Neprilysin (838 Activities)

Discover Target: MME

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC15A1 Tchem Oligopeptide transporter small intestine isoform (922 Activities)

Discover Target: SLC15A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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Tpp2 Tripeptidyl aminopeptidase (141 Activities)

Discover Target: Tpp2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Molekulargewicht: 236.270 g/mol
• XLogP3: -2.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 236.116 Da
• Monoisotopic Mass: 236.116 Da
• Topological Polar Surface Area: 92.400 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 275.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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

Manufacturer-validated protocols are not provided for this item. Common research workflows include:

• Preparation of aqueous stock solutions (e.g., 10–100 mM) followed by sterile filtration (0.22 µm) for biological assays.
• HPLC method development using C18 reversed-phase columns, monitoring UV at ~257–260 nm (phenylalanine absorbance; literature), with water/acetonitrile gradients containing 0.1% formic acid or TFA.
• Peptide coupling to extend sequences: dissolve Ala–Phe in dry DMF, activate with HATU/DIPEA, and couple to amine-bearing partners; monitor by LC–MS.

Adjust conditions to your system and consult the primary literature or internal SOPs for detailed steps.

Biological Roles

Note: For research use only. The following describes general biochemical roles of the alanyl–phenylalanine dipeptide; it does not imply suitability for clinical use.

• Metabolic context: Dipeptides like Ala–Phe arise during proteolysis and are further processed by peptidases to free amino acids. Transport across membranes can occur via proton-coupled oligopeptide transporters (e.g., PepT1/PepT2), which recognize many neutral dipeptides.
• Structure–function features: Combines a small aliphatic residue (Ala) with an aromatic residue (Phe), offering a model for studying hydrophobic interactions, π-stacking with aromatic residues, and backbone hydrogen bonding.
• Uptake/utilization studies: Used as a probe to investigate dipeptide transport kinetics, binding energetics, and competition with other di-/tripeptides in cell or vesicle systems.
• Enzyme substrates: Serves as a non-derivatized backbone for generating chromogenic/fluorogenic substrates (e.g., pNA/AMC-labeled derivatives) to quantify exopeptidase or dipeptidase activity.
• Spectroscopic behavior: The phenylalanine ring provides useful UV absorbance near 257–260 nm (literature) for monitoring uptake or hydrolysis via HPLC/UV.

Selection notes: The exact stereochemistry can modulate transporter recognition and enzymatic turnover. Unless specified for this item, confirm stereochemical configuration on the CoA before use in biological assays.

Buffer Applications

Ala-Phe is not itself a buffering agent. However, successful use frequently depends on choosing compatible buffers for dissolution, storage, and assays.

• Dissolution buffers (general):
  • Phosphate-buffered saline (PBS), pH 7.2–7.4: Routine compatibility with cells/enzymes.
  • HEPES, pH 7.0–8.0: Good pH stability in open systems (low CO2 sensitivity).
  • Tris, pH 7.5–8.5: Useful for enzyme assays; note Tris can interact with some coupling chemistries.
• Ionic strength: Moderate ionic strength (50–150 mM) typically aids solubility and mimics physiological conditions.
• pH adjustment: Slight basification (pH 7.5–8.0) often enhances dipeptide dissolution; adjust minimally to avoid altering assay conditions.
• Sterile handling: For cell-based or microbiological assays, dissolve in sterile buffer and 0.22 µm filter; store aliquots at −20°C to limit contamination.

Recipes are assay-dependent; validate buffer composition and pH against your enzymatic or transport model requirements.

Green Alternatives

As a solid dipeptide, Ala-Phe itself is not readily replaced; however, greener choices relate to solvent and reagent selection in its handling and downstream chemistry.

Greener considerations (general):

• Prefer aqueous buffers for dissolution and biochemistry where feasible; minimize DMSO/DMF content.
• For peptide couplings, consider less hazardous coupling systems and solvent choices (e.g., use ethyl acetate or 2-MeTHF where compatible; water-promoted couplings with water-soluble carbodiimides like EDC in buffered media).
• Minimize protecting groups and steps to reduce solvent/reagent consumption.

Illustrative comparison (general guidance):

| Aspect | Conventional option | Greener alternative | Trade-offs | |---|---|---|---| | Stock solution | DMSO | Water/PBS | May require pH adjustment; lower max solubility | | Coupling solvent | DMF/DCM | 2-MeTHF/EtOAc or aqueous EDC systems | Solubility/reactivity may differ; optimization needed | | Coupling reagent | HATU, PyBOP (hazardous byproducts) | EDC·HCl + NHS (aqueous-compatible) | Sometimes lower coupling efficiency; careful pH control | | Workup | Large-volume halogenated washes | Non-halogenated solvents, aqueous crystallization | Purity/yield balance may change |

Adopt DoE to optimize greener conditions while maintaining yield and stereochemical integrity.

Pharmaceutical Uses

No therapeutic claims are made. The following reflects general formulation/manufacturing contexts for small peptides.

• Excipient status: Ala-Phe is not a common pharmacopeial excipient. When used, small dipeptides may function as model compounds in permeability, stability, and taste-masking research, not as approved additives.
• Preformulation studies: Dipeptides like Ala–Phe are used to probe peptide transporters and to evaluate peptide stability in simulated gastric/intestinal fluids, informing formulation strategies for peptide-based actives.
• Process development: Serves as a surrogate to optimize peptide purification (RP-HPLC gradients, lyophilization cycles) and solid-form selection (salt vs free acid) before applying to higher-value actives.
• Analytical development: Useful as a system suitability or method development standard for peptide LC methods thanks to its single aromatic residue and moderate polarity.

For any use in regulated products, confirm identity, purity, residual solvents, optical configuration, and bioburden/endotoxin as applicable. This catalog item is for research use only.

Physical Properties

Item-specific physicochemical specifications were not provided. The following points summarize general/literature characteristics for alanyl–phenylalanine; do not construe as product specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Typically an off-white to white crystalline solid for many dipeptides.)
• Molecular weight (literature, H-Ala-Phe-OH): ~236.27 g/mol
• Acid–base behavior (general): Zwitterionic near neutral pH; the terminal carboxyl group (pKa ~2–3, literature for peptides) and terminal amino group (pKa ~8–9, literature) govern solubility/charge state.
• Solubility (general):
  • Water/buffers: Readily soluble to moderately soluble; solubility often improves with slight pH adjustment (e.g., pH 7–8) or gentle warming.
  • Alcohols: Limited to moderate solubility in methanol/ethanol (literature, peptide-dependent).
  • Polar aprotic (DMF, DMSO): Generally soluble.
  • Nonpolar solvents (e.g., hexane, toluene): Essentially insoluble.
• Partitioning: Expected low logP due to zwitterionic character in water (literature trend for small peptides).
• Melting point/thermal behavior: Often high melting with possible decomposition for dipeptides (specific value not assigned here).

All numerical values, if required for method development, should be verified experimentally or by consulting the item’s CoA/Spec Sheet.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Typical peptide-related quality attributes (general):
  • Purity determination by HPLC/UPLC with UV detection; supplementary identity by HRMS and, when relevant, NMR.
  • Counter-ion content (if provided as a salt), residual solvents, and water content (Karl Fischer) may be reported for peptide materials; Not specified for this item.
  • Optical purity/enantiomeric composition (e.g., L/L vs D/L) assessed by chiral HPLC or specific rotation; Not specified for this item.
• Stabilizers/additives: Not specified for this item; if present, will be indicated on CoA/Spec Sheet.
• What the grades typically imply (general context):
  • Research grade peptide building blocks are produced to support synthetic and biochemical workflows, emphasizing chromatographic purity and identity confirmation.
  • Peptide synthesis grade materials may be supplied with tight limits on inorganic/organic impurities and controlled residual solvent profiles to ensure coupling efficiency.

For method-critical applications (e.g., quantitative enzymology), confirm actual purity, water content, and counter-ion form on the supplied CoA.

Reaction and Applications

Ala-Phe is widely used as a small-peptide tool compound and building block.

Research and analytical applications (general):

• Enzymology: Substrate or reference dipeptide in assays of peptidases/dipeptidyl peptidases and peptide transporters (e.g., PepT systems). Often derivatized (e.g., chromogenic/fluorogenic) for kinetic readouts.
• Chromatography: Retention behavior serves as a benchmark in peptide HPLC method development; can calibrate peptide mapping gradients.
• Biophysics: Model for studying peptide bond isomerization, hydrogen bonding, and aromatic–aliphatic side-chain interactions.

Synthetic applications (general):

• Peptide elongation: Acts as an N-terminally free dipeptide (H-Ala-Phe-OH) that can be coupled at its C-terminus to furnish tripeptides via standard coupling reagents (EDC/HOBt, HATU, PyBOP) with bases such as DIPEA.
• Derivatization: Carboxyl activation (e.g., mixed anhydrides, active esters) or N-acylation to form protected intermediates. Side-chain chemistry is minimal (benzyl phenylalanine ring is inert under many peptide conditions).
• Conjugation: Can be linked to dyes, affinity tags, or polymers through the terminal amine or carboxyl group.

Practical tips:

• Control epimerization at the C-terminus during coupling by using fast-acting reagents (e.g., HATU) at low temperature and short activation times; add base last.
• Maintain low water content in coupling solvents (DMF/DCM) to preserve reagent activity; sparge with inert gas if needed.
• For analytical assays, prepare fresh aqueous stocks or aliquot and freeze to prevent hydrolysis/microbial growth.

Reaction Conditions

General literature guidance for coupling and derivatizing H-Ala–Phe–OH (adjust to your substrate and scale):

• Fragment coupling to amines (amide formation):

  • Solvent: DMF (anhydrous) or NMP; for greener options, 2-MeTHF/EtOAc may be used with careful solubility checks.
  • Activation: HATU (1.0–1.2 equiv) or EDC·HCl (1.2–1.5 equiv) + Oxyma/HOAt (1.0–1.2 equiv).
  • Base: DIPEA (2–3 equiv) for uronium reagents; minimal base for EDC to reduce O-acylisourea rearrangements.
  • Temperature: 0–25°C (start cold to reduce racemization); 0.5–3 h typical for small fragments.
  • Atmosphere: Inert gas recommended for moisture-sensitive reagents; peptides themselves are air-stable.
  • Typical outcomes (literature ranges): 70–95% isolated for clean fragment couplings under optimized conditions.

• NHS ester formation (pre-activation):

  • Reagents: EDC·HCl (1.2–1.5 equiv) + NHS (1.2–1.5 equiv) in DMF or DCM with catalytic DMAP (optional).
  • Temp/time: 0–25°C, 0.5–2 h; use immediately or store at low temperature, protected from moisture.

• N-terminal protection (e.g., Boc):

  • Reagents: Boc2O (1.1–1.5 equiv) in aqueous dioxane or THF with NaHCO3 or Na2CO3; 0–25°C, 1–3 h.

• Aqueous bioconjugation (carbodiimide):

  • Buffer: MES or acetate, pH 5.0–6.0; add EDC then NHS; introduce amine partner promptly; 0–25°C.

All parameters are general literature guidance; optimize for your specific substrates and stereochemistry control.

Safety and Handling

• GHS classification, H/P statements, and pictograms: Not specified for this item; refer to the product SDS for authoritative hazard information.
• Expected hazards (general for small peptides): Low volatility, low acute hazard profile compared to many organic reagents; may cause irritation to eyes/skin/respiratory tract as particulate.
• Personal protective equipment (PPE): Laboratory coat, safety glasses, and appropriate gloves (e.g., nitrile). Handle powders in a fume hood or ventilated enclosure to minimize dust inhalation.
• Handling notes:
  • Avoid generating dust/aerosols. Use clean, dry tools and dedicated weighing paper to prevent cross-contamination.
  • For sterile applications, reconstitute with sterile-filtered water or buffer; 0.22 µm filtration is common.
• Incompatibilities (general): Strong oxidizers; strong acids/bases may hydrolyze peptide bonds under forcing conditions.
• First-aid overview (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention if unwell.
• Fire safety: Nonflammable solid in most contexts; if involved in fire, use water spray, CO2, foam, or dry chemical. Thermal decomposition may produce nitrogen oxides and carbon oxides.

Always consult the SDS for definitive guidance.

Solvent Selection

Ala-Phe is a polar, zwitterionic dipeptide. Solvent choice should balance solubility, downstream compatibility, and potential impact on peptide/protein assays.

• Polarity/miscibility (general):
  • Water, PBS, and other physiological buffers: Typically first choice; good solubility at neutral to slightly basic pH.
  • DMSO and DMF: Excellent solvating power for stock solutions; dilute promptly into aqueous media to minimize solvent effects.
  • Alcohols (MeOH, EtOH): Variable solubility; may be useful for co-solvent strategies.
  • Nonpolar solvents (DCM, toluene, hexanes): Not suitable.
• Practical guidance:
  • Begin with water or buffer at pH 7.0–8.0; adjust pH with minimal NaOH if needed to achieve dissolution, then readjust to target pH.
  • For high-concentration stocks, prepare in DMSO or DMF (e.g., 100–500 mM), then serially dilute into assay buffer, keeping final organic content ≤1–2% v/v where required.
  • Warm (room temperature to 37°C) and gentle vortex/sonication can aid dissolution; avoid prolonged heating.

Comparison (general use-cases):

• Water/PBS: Biologically compatible; minimal matrix effects; limited maximum solubility for some dipeptides.
• DMSO: High solubility; can affect some enzymes/cells at >1–2% v/v.
• DMF: Strong solvent for coupling chemistry; hygroscopic and less biocompatible than DMSO.

Select the solvent system according to downstream biology or synthetic application requirements.

Storage and Reconstitution

• Storage conditions (item-specific): Store at −20°C.
• Shipping (item-specific): Shipped in ice chest with ice pads.
• Protect from: Moisture and microbial contamination. Keep container tightly closed. Desiccation is recommended for long-term stability.

Reconstitution (general guidance):

• Solvents: Water, PBS, or assay buffer are preferred. DMSO or DMF can be used to prepare concentrated stocks if required.
• Procedure:
  1. Allow vial to equilibrate to room temperature in a desiccator before opening to minimize moisture uptake.
  2. Add calculated solvent volume to achieve desired concentration; gentle vortex and, if needed, brief sonication. Adjust pH slightly (7.5–8.0) to aid dissolution, then readjust to target pH.
  3. For sterile applications, 0.22 µm filter the solution into sterile aliquots.
• Aliquoting and stability:
  • Prepare single-use aliquots; store at −20°C (short term) or −80°C (long term) to minimize freeze–thaw cycles.
  • Avoid repeated freeze–thaw; thaw on ice and use promptly. Typical aqueous stocks are most stable for days to a few weeks, depending on pH and bioburden—verify by analytical HPLC.

For exact shelf life, residual solvent limits, and any stabilizers, refer to the item’s CoA/Spec Sheet. For safety information, consult the SDS.

Structure and Identity

Ala-Phe is the dipeptide alanyl–phenylalanine, typically encountered as the free acid H-Ala-Phe-OH (stereochemistry often L/L in biochemical contexts, but not specified for this item).

• SKU: A121378
• CAS: 3061-90-3 (commonly assigned to alanyl-phenylalanine)
• PubChem CID: 96814
• InChIKey (as provided): 261920
• SMILES: Not specified for this item; refer to CoA/Spec Sheet. (Literature examples for H-Ala-Phe-OH exist but stereochemistry may vary.)
• Molecular formula (literature, for H-Ala-Phe-OH): C12H16N2O3
• Molecular weight (literature, for H-Ala-Phe-OH): ~236.27 g/mol

Structural features (general description):

• Dipeptide consisting of an N-terminal alanine residue linked via an amide bond to a C-terminal phenylalanine residue.
• Functional groups: one secondary amide (peptide bond), one terminal carboxylic acid, one terminal amine (zwitterionic at neutral pH), and one phenyl ring (from phenylalanine side chain).
• 2D structure in words: CH3–CH(NH2)–CO–NH–CH(CH2–Ph)–CO2H, with the amide carbonyl between Ala and Phe and an aromatic benzyl side chain on the Phe α-carbon.

Note on stereochemistry: Unless explicitly stated, the absolute configuration (e.g., L-Ala–L-Phe vs D/L variants) is not specified for this item; refer to CoA/Spec Sheet.

Synthetic Utility

Ala-Phe (H-Ala-Phe-OH) is a versatile intermediate for constructing longer peptides and peptide conjugates.

Key functional elements and reactivity:

• C-terminal carboxylic acid: Activates to O-acyl intermediates (e.g., NHS esters) for amide bond formation with amines; susceptible to racemization if over-activated.
• N-terminal amino group: Amenable to acylation, carbamate formation, or protection (e.g., Boc-, Fmoc-, Cbz-). Selective N-acylation enables fragment coupling strategies.
• Peptide bond: Generally inert under neutral conditions; hydrolyzes under strong acid/base or enzymatic action.

Named/standard transformations (general):

• Carbodiimide couplings (EDC/HOBt or EDC/NHS; DIC/Oxyma).
• Uronium/phosphonium-mediated couplings (HATU, TBTU, PyBOP) with DIPEA.
• Mixed anhydride or acid chloride formation (in situ) for rapid fragment condensation.

Retrosynthetic value:

• Allows convergent assembly: pre-form Ala–Phe, then couple to either N- or C-terminal fragments to reduce step count in solid- or solution-phase synthesis.
• Orthogonal protecting groups on N-terminus (e.g., Fmoc-Ala–Phe-OH) can be introduced to integrate with SPPS workflows.

Practical notes:

• Minimize epimerization by short activation times, low temperature (0–10°C), and use of Oxyma or HOAt analogs.
• For aqueous bioconjugations, EDC in MES buffer (pH ~5.0–6.0) efficiently forms amide bonds to amines on biomolecules.

Target Specificity

Not applicable to this product type. No antigen/epitope or biological target specificity is provided for this item.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 3061-90-3, the molecular formula is C12H16N2O3, and the molecular weight is 236.27 g/mol. InChIKey OMNVYXHOSHNURL-WPRPVWTQSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.