This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
159.230 g/mol
XLogP3
-1.000
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
5
Exact Mass
159.126 Da
Monoisotopic Mass
159.126 Da
Topological Polar Surface Area
63.300 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
128.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
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
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Recensioni
Recensioni dei clienti
Application Protocols
Not applicable to immunoassay formats (WB, IHC, IF, FC) as this is a small-molecule building block.
General laboratory use notes:
For coupling into peptides, dissolve in dry DMF or DCM/DMF mix and proceed with the chosen coupling system (see Reaction Conditions). Perform a small-scale test (5–50 mg) to confirm solubility and reactivity before scale-up.
For salt preparation (amine variant), titrate with standardized acid or base while monitoring pH and precipitation/crystallization behavior.
For analytical methods, develop an RP-HPLC gradient (e.g., water + 0.1% formic acid/acetonitrile) and confirm identity by LC-MS and NMR. Adjust pH and ion-pairing only after confirming the exact isomer supplied.
No tested biological application protocols are provided for this SKU.
Biological Roles
This product is supplied strictly for research use. No clinical or diagnostic use is intended.
General/literature context (not item-specific):
Dipropyl-substituted glycine derivatives are noncanonical amino acids. They are not naturally encoded and generally do not participate in standard metabolic pathways.
α,α-Disubstituted amino acids can stabilize secondary structure elements in peptides (e.g., bias toward specific φ/ψ torsions), thereby influencing peptide–protein interactions in mechanistic studies.
Tertiary-amine glycine derivatives (if N,N-dipropyl) can act as zwitterions or form salts at physiological pH, and are used as probes of transport, permeability, or as components in synthetic analogs of osmolytes, but they are not known natural metabolites.
Enzymatic processing: canonical aminoacyl-tRNA synthetases and peptidases typically do not accept bulky α,α-disubstituted substrates; such residues can render peptides more resistant to enzymatic degradation (literature observation in peptidomimetic chemistry).
Researchers should determine suitability experimentally for their specific biochemical assays and confirm the precise structure of the supplied compound via the CoA/Spec Sheet before drawing biological conclusions.
Buffer Applications
Not typically used as a primary buffering agent.
General guidance (if using in aqueous systems):
As an amino acid derivative, it may contribute to solution ionic strength or act as a co-solute, but it does not constitute a standard buffer system with a defined pKa range like Tris, HEPES, or phosphate.
If the tertiary amine variant is supplied (N,N-dipropylglycine), it can be converted to a defined salt (e.g., hydrochloride) for improved aqueous solubility; however, buffering capacity and pKa values must be experimentally measured for the specific isomer and salt form.
For robust buffering in biochemical assays, prefer established buffers (e.g., phosphate pH 6–8, HEPES pH 6.8–8.2, acetate pH 3.8–5.8) and include dipropylglycine only as a substrate/solute as needed.
Item-specific pKa and buffer recipes: Not specified for this item; refer to CoA/Spec Sheet or determine empirically.
Green Alternatives
Greener practice opportunities revolve around solvent choice, coupling reagents, and protection strategies rather than the building block itself.
Replace DMF/NMP with safer alternatives where feasible: Cyrene, propylene carbonate, dimethyl sulfone, or 2-MeTHF/EtOAc for extractions and some couplings.
Use water or water/ethanol for salt formation, crystallizations, and ion-exchange steps when solubility permits.
Coupling reagents:
Favor water-compatible carbodiimide systems (EDC·HCl with OxymaPure) over benzotriazole-based reagents where possible to reduce potentially explosive waste streams.
Consider catalytic coupling strategies (e.g., DMTMM in MeOH/H2O) for simple amide formations.
Energy and waste minimization:
Employ pH-switch crystallizations instead of chromatographic purification when feasible.
Explore mechanochemical couplings (ball milling) to lower solvent usage.
Illustrative comparison (general):
Traditional: DMF + HATU/HBTU + DIPEA (efficient but hazardous solvent and energetic reagents).
Greener: EtOAc/2-MeTHF or aqueous ethanol + EDC/Oxyma or DMTMM; reduced solvent toxicity, simpler aqueous workup.
Note: Actual feasibility depends on which dipropylglycine isomer is supplied; perform small-scale solubility and reactivity screens before process commitment.
Pharmaceutical Uses
No therapeutic claims are made. For research and laboratory use only.
Formulation and process context (general, not item-specific):
As a noncanonical amino acid building block, dipropylglycine derivatives may be incorporated into investigational peptide leads to alter conformation and proteolytic stability during early discovery research.
Tertiary-amine glycine derivatives can form crystalline salts with mineral or organic acids; such salts may be explored for solubility enhancement studies or as counterions in experimental formulations.
Excipiency: There is no pharmacopeial monograph known for “dipropylglycine” as a general excipient. Any use in preformulation must be supported by full analytical characterization (identity, purity, residual solvents, polymorph/solvate state, and salt form where applicable).
Analytical development: develop stability-indicating methods (HPLC/UPLC) to track degradation (e.g., amide hydrolysis of derivatives, decarboxylation under strong heating, or N-oxide formation for tertiary amines in oxidative stress).
Regulatory note: Any progression beyond bench-scale research requires comprehensive safety, impurity, and stability evaluation under applicable guidelines. This catalog item is provided solely for research use.
Physical Properties
Item-specific specifications (this SKU):
Boiling point, melting point, density, refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
Solubility: Not specified for this item; refer to CoA/Spec Sheet.
General/literature guidance (will differ by isomer; verify against CoA):
Acid–base behavior: amino acid derivatives typically exist as zwitterions near neutral pH; N,N-dialkylglycines are more basic at nitrogen and can form water-soluble salts with mineral acids, whereas α,α-disubstituted amino acids may be less soluble in water but more soluble in polar aprotic solvents.
Partitioning: introduction of two n-propyl groups increases hydrophobicity relative to glycine; expect increased logP vs. glycine (literature trend, isomer-dependent).
Thermal behavior: amino acids generally show decomposition before boiling; many α,α-disubstituted amino acids have definable melting points, while tertiary-amine glycine derivatives may be low-melting solids or oils (literature trend; confirm for this item).
Hygroscopicity: tertiary amine forms (if present) can absorb CO2/H2O to form ammonium carboxylate species; store tightly sealed to minimize atmospheric uptake.
Note: Use the item’s CoA/Spec Sheet for any quantitative values needed for method development, QC, or regulatory documentation.
Quality and Grades
Grade/Purity for this SKU: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
In the absence of a stated grade, the CoA/Spec Sheet should be considered the primary quality reference (assay method, purity by HPLC/GC/NMR, residual solvents, and water content if applicable).
If the product is intended as a building block for peptide or small-molecule synthesis, review: identity confirmation (1H/13C NMR, HRMS), chiral purity (if chiral center is present), and inorganic/metal residue if catalytic steps are anticipated downstream.
UV background: if planning to use the material in analytical methods (HPLC/UPLC detection), confirm UV absorbance cutoff and impurity profile on the CoA; do not assume HPLC grade characteristics unless explicitly specified.
Stabilizers/inhibitors: None stated for this item. If your application is moisture- or CO2-sensitive (e.g., free-base tertiary amine), verify whether the supplied form is free base or salt and whether any stabilizer is present.
Lot-to-lot consistency: retain a portion of each lot for internal cross-validation in critical synthetic routes; document water content and counterion identity (if a salt) prior to scale-up.
Reaction and Applications
Manufacturer applications: Not specified in the catalog entry beyond “For research use only.”
General applications for dipropylglycine-type building blocks (literature context; confirm structure for this SKU):
Peptide and peptidomimetic synthesis: α,α-disubstituted amino acids (e.g., 2,2-dipropylglycine) are used to modulate backbone conformations, reduce proteolysis, and probe steric effects in bioactive sequences.
Ligand/auxiliary design: N-acylated derivatives can serve as chiral environment modifiers or influence stereochemical outcomes in amide-forming or metal-mediated transformations when a chiral variant is employed.
Surfactant-like derivatives: conversion to amide/ester/zwitterionic forms can yield amphiphiles or task-specific phase-transfer agents (tertiary amine variants).
Salt formation and ion-pairing: tertiary-amine glycine derivatives are convenient for forming ionic liquids or ion-pair reagents after quaternization.
Practical notes:
Coupling chemistry: activate the carboxyl group with carbodiimides (EDC/DIC) or uronium salts (HATU/HBTU) with bases (DIPEA) under anhydrous conditions; include racemization suppressors if a chiral center exists.
Protection: choose orthogonal protecting groups suitable for the specific isomer (Boc/Alloc/Fmoc on nitrogen if primary amine present; convert tertiary amine to salt if N-protection is not possible). Carboxyl protection as methyl/benzyl esters facilitates multi-step sequences.
Purification: use ion-exchange or pH-switch liquid–liquid extraction; preparative RP-HPLC for polar salts.
Always confirm the exact isomer provided before committing to route design.
Reaction Conditions
Item-specific conditions are not defined for this SKU. The following are general literature-guided starting points; optimize for your system and confirm the isomer supplied.
Amide coupling (forming amide from carboxyl group):
Temperature/time: 0–25 °C, 1–16 h. Monitor by LC-MS.
Esterification (carboxyl group → methyl/benzyl ester):
Fischer: MeOH or BnOH with catalytic H2SO4 or p-TsOH, reflux 2–24 h (water removal improves yield).
Acid chloride route: SOCl2/oxalyl chloride (1.5–3 eq) in DCM, 0–25 °C, 1–3 h, then alcohol and base.
Quaternization (tertiary amine variant):
Alkyl halide (1.1–1.5 eq) in MeCN/acetone, 25–60 °C, 2–24 h to form ammonium salt.
Salt formation (amine variant):
Dissolve in minimal alcohol or EtOAc, add HCl(g) or HCl in dioxane; crystallization at 0–5 °C.
Hydrogenolysis (for benzyl esters):
Pd/C (5–10 wt%), H2 (1–3 bar), MeOH/EtOH, 25 °C, 1–6 h.
Notes:
For chiral α,α-disubstituted amino acids, include racemization suppressors (HOAt/Oxyma) and maintain ≤25 °C.
Control pH carefully during workup to isolate the desired free acid, free base, or salt form.
Safety and Handling
Item-specific GHS details for this SKU:
Signal word, hazard statements, pictograms, and GHS classification: Not specified for this item; refer to SDS.
General safety guidance (consult SDS for authoritative instructions):
Likely hazards: amino acid derivatives with dialkyl substituents can be irritants to skin/eyes; tertiary amines may be corrosive to eyes and harmful if swallowed or inhaled (hazard level varies by structure and purity).
Personal protective equipment: lab coat, nitrile gloves, and safety glasses as baseline. Use splash goggles and face protection if handling solutions at scale. Employ local exhaust ventilation when weighing or charging reactors.
Handling: avoid dust/airborne particulates. For tertiary amines, minimize exposure to air/CO2 to avoid salt formation; keep containers tightly closed.
Incompatibilities: strong oxidizers; strong acids/bases (can form salts or lead to decomposition). Tertiary amines may react with acylating agents, sulfonyl chlorides, and alkyl halides—avoid unintended derivatization.
First aid overview: in case of skin/eye contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Provide SDS to responders.
Fire safety: many organic solids/oils are combustible. Use CO2, dry chemical, or foam. Combustion may produce COx, NOx.
Waste: dispose of according to institutional and local regulations. Segregate amines/acids from oxidizers.
For research use only.
Solvent Selection
Item-specific solubility/miscibility: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for dipropyl-substituted glycine derivatives (verify with a small-scale solubility screen):
Likely solvent classes:
Polar protic: water, methanol, ethanol—solubility depends strongly on ionization state. Tertiary amine (N,N-dipropylglycine) is often more soluble as an acid salt (e.g., HCl salt) in water/alcohols.
Polar aprotic: DMF, DMSO, NMP commonly dissolve both free acids and salts; useful for coupling chemistry.
Moderately polar: acetonitrile, ethyl acetate may dissolve neutral forms; salified forms are typically less soluble.
pH leverage: converting to a salt (e.g., hydrochloride) increases aqueous solubility for amine-containing forms; neutralization reduces water solubility and can aid extraction into organic solvents.
Comparison (typical, literature-based):
Versus glycine: dramatically lower water solubility expected due to hydrophobic propyl groups unless ionized.
Versus sarcosine/betaine: higher hydrophobicity and lower aqueous solubility at neutral pH.
Practical tips:
For LC method development, begin with aqueous buffer (pH 2–3 for amine salts) and acetonitrile gradient; monitor for secondary interactions.
For workups, use pH-switching (acid/base) to shuttle between aqueous and organic phases as needed, taking care to avoid emulsions with long-chain substituents.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance:
Keep tightly closed in a dry, well-ventilated place. Protect from moisture and CO2, especially if the product is a tertiary amine free base, to prevent salt formation and caking.
If supplied as a salt (e.g., HCl), store in the original container to minimize humidity uptake.
Reconstitution/solubilization: choose solvent based on intended use—dry DMF, DMSO, MeOH, or aqueous acid/base depending on whether the free acid or amine salt is targeted. Filter (0.2 µm) solutions intended for chromatographic or biochemical use.
Stability: Without item-specific data, prepare solutions fresh when possible. For stock solutions in DMSO/DMF, store aliquots in sealed vials under inert gas at 2–8 °C or −20 °C to extend shelf life; verify stability by HPLC prior to critical experiments.
Avoid repeated freeze–thaw of solutions. Label containers with preparation date, solvent, and concentration.
Always consult the product’s CoA and SDS for definitive instructions and stability information.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
General structural notes (chemistry background):
The name “dipropylglycine” is used in the literature for two distinct structural motifs:
N,N-dipropylglycine (a tertiary amine carboxylic acid, i.e., glycine with two n-propyl groups on nitrogen).
2,2-dipropylglycine (an α,α-disubstituted amino acid with two n-propyl groups at the α-carbon, often abbreviated Dpg).
These two isomers have distinct physicochemical and reactivity profiles (e.g., basicity, sterics at nitrogen vs. α-carbon). Verification against the CoA/Spec Sheet is recommended to confirm the exact structure supplied under this SKU.
Functional groups expected (depending on isomer): a carboxylic acid (–CO2H) and either a secondary amine center substituted with two propyl chains (tertiary amine overall) or a primary amine bound to a quaternary α-carbon bearing two propyl groups.
2D description (generic): an amino acid backbone (–NH–CH(R)–CO2H or NR2–CH2–CO2H) where R represents propyl substituents positioned either on nitrogen (N,N-dipropyl) or on the α-carbon (α,α-dipropyl).
Synthetic Utility
General synthetic roles (literature-based; confirm isomer per CoA):
Building block for amide/peptide synthesis: couples to amines via standard coupling agents (EDC/DIC/HATU/HBTU/T3P). α,α-Disubstituted variants introduce steric bulk at Cα, altering conformational bias and often reducing racemization.
Protecting-group chemistry: if the amine is primary (α,α-disubstituted case), use Boc/Fmoc/Alloc as appropriate; if tertiary amine (N,N-dipropyl), nitrogen protection is not feasible—use salt formation or quaternization for temporary modification.
Quaternary ammonium chemistry: tertiary-amine variants undergo alkylation to give quaternary ammonium carboxylates (or betaine-like zwitterions) useful in phase-transfer or ion-pairing applications.
Derivatization handles: carboxyl group can be converted to esters, acyl chlorides (via oxalyl chloride/SOCl2), or activated esters (pNP, NHS, PFP) for bioconjugation.
Retrosynthetic value: dipropylglycine can be traced back to glycine equivalents via dialkylation (for N,N-dipropyl) or to α-alkylation strategies using strong bases and propyl electrophiles (for α,α-dipropyl), noting the need for chiral control if asymmetry is desired.
Tips:
Ensure thorough drying of polar aprotic solvents (DMF/DMSO) for coupling. Use molecular sieves or azeotropic drying for esterifications.
For scale-up, prefer T3P or EDC/Oxyma to minimize hazardous waste compared to benzotriazole-based reagents.
Target Specificity
Not applicable. This product is a small-molecule amino acid derivative and does not possess antibody/biomolecule target specificity attributes (no antigen/epitope, clone, isotype, or species reactivity). Researchers should refer to Reaction & Applications and Synthetic Utility for relevant chemical-use guidance.
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