This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
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.
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Application Protocols
No item-specific tested application protocols are provided in the Product Data. The following are general, non-binding examples to guide laboratory use.
Stock solution preparation (analytical assays):
Dissolve in water or DMSO to prepare a 10–100 mM stock (as solubility allows). Filter (0.22 µm) if particulate is present. Store aliquots to minimize freeze–thaw.
Coupling to an amine (general EDC protocol):
Dissolve N-Acetyl-D-Proline (1.0 eq) and the amine partner (1.0–1.2 eq) in DMF (or MeCN).
Add EDC·HCl (1.1 eq) and a catalytic amount of Oxyma or HOAt-analog; include base (DIPEA, 2.0 eq).
Stir at 0–25 °C, monitor by LC. Quench, dilute with water, extract or precipitate product, and purify by chromatography or crystallization.
Esterification (Steglich):
In DCM, cool to 0 °C; add alcohol (1.5 eq), DCC (1.1 eq), and catalytic DMAP. Warm to rt and stir until completion. Filter DCU and purify.
Adjust concentrations, equivalents, and temperatures based on your substrate and scale. Perform small-scale trials to optimize conditions and confirm stereochemical integrity. For research use only.
Biological Roles
This product is intended for research use only. The following notes describe general biochemical context for N-acetylated amino acids and proline derivatives; they are not medical or clinical claims.
Biochemical context (literature/general):
N-Acetylation of amino groups is a common modification that decreases basicity and nucleophilicity. For proline, N-acetylation yields a neutral amide and a free carboxyl group, altering charge state and solubility across pH.
Proline residues influence protein folding due to conformational constraints of the pyrrolidine ring; acetylated proline derivatives are often used as models to study peptide bond isomerization (cis/trans) and ring puckering.
D-enantiomers of amino acids are rare in metazoan proteins but occur in bacterial cell walls and certain peptides; D-proline derivatives are used to probe stereochemical recognition in enzymes and transporters.
Experimental uses:
Standards in chiral chromatography method development (separation of D/L amino acid derivatives).
Model substrates in studies of amide bond kinetics, proline cis/trans isomerization, and conformational analysis by NMR/IR.
Metabolic handling:
Compared to the parent amine, N-acetyl derivatives typically show altered enzymatic susceptibility (e.g., are not substrates for transamination at the free amine). Specific metabolic pathways for N-Acetyl-D-Proline vary by organism and are context-dependent.
No specific biological activity or target interactions are claimed for this catalog item.
Buffer Applications
N-Acetyl-D-Proline is not a conventional buffering agent. It lacks a free amine and presents a single titratable carboxyl group, offering limited buffering capacity except in a narrow acidic range.
Practical notes (general):
Can be dissolved in aqueous media; pH adjustment (e.g., with NaOH) will form the carboxylate salt, improving solubility.
If used as an additive (e.g., chiral selector studies), prepare solutions in standard buffers (phosphate, acetate, citrate) rather than relying on this compound for buffering.
For robust buffering needs, choose established systems (phosphate pH 6–8, acetate pH 3.6–5.6, citrate pH 3–6.2). No item-specific buffer recipes are provided.
Green Alternatives
Opportunities to improve sustainability when working with N-Acetyl-D-Proline relate mainly to solvent and coupling-reagent choices rather than the substrate itself.
Greener solvent choices (literature/general):
Prefer water or water–ethanol mixtures for dissolution, crystallization, and some esterifications (biocatalytic routes).
Replace DMF/NMP where possible with safer polar aprotics such as propylene carbonate or Cyrene (dihydrolevoglucosenone) after solubility assessment.
Greener coupling strategies:
Use water-tolerant carbodiimides (EDC) with catalytic NHS/HOAt alternatives (where permitted) to minimize hazardous waste compared to DCC/DCU protocols.
Explore enzyme-catalyzed amidations/esterifications in aqueous media or deep eutectic solvents.
Comparison snapshot (general):
DMF vs ethanol/water: DMF offers broader solubility but is a reproductive toxin and harder to remove; ethanol/water are benign but may require pH control and can limit substrate scope.
DCC vs EDC: DCC generates insoluble urea waste (DCU) and can be sensitizing; EDC forms water-soluble urea byproducts, easing work-up.
Tradeoffs: Greener systems may reduce reaction rates or scope; pilot small-scale screens to balance EHS benefits with performance.
Note: No item-specific solvent or reagent restrictions are specified; adapt choices to your process and consult institutional green-chemistry guidelines.
Pharmaceutical Uses
For research use only; not for human or veterinary use. The following discusses general formulation/manufacturing contexts without therapeutic claims.
Possible roles (literature/general):
Intermediate/building block in the synthesis of peptidomimetics or prodrug moieties where a D-proline unit with a blocked amine is required.
Chiral auxiliary/handle incorporated into small molecules to influence conformation or solubility.
Excipient status:
N-Acetyl-D-Proline is not a common pharmacopeial excipient. No compendial monograph is implied by this listing.
Developability considerations:
Solubility can be tuned via salt formation of the carboxylate (e.g., sodium salt) or by esterification for prodrug strategies in research settings.
Analytical control: chiral purity (ee), residual solvents, and polymorph/solid form (if applicable) should be evaluated during process development.
Item-specific regulatory grade or GMP suitability is not specified; consult the CoA/Spec Sheet and your QA unit for appropriate use categorization.
Physical Properties
Item-specific specifications are not listed in the Product Data. The following points are general/literature guidance about N-acetylated proline derivatives and should not be construed as product specifications for this SKU.
Aggregated state/appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Acid–base properties (literature):
Carboxylic acid pKa expected in the typical range for N-acylated amino acids; the amide nitrogen is non-basic under normal conditions.
Predominantly exists as a neutral acid (or zwitterionic form in water depending on pH); no free amine due to acetylation.
Solubility (literature/general):
Generally soluble in water and polar protic solvents (e.g., methanol, ethanol) and in some polar aprotics (e.g., DMF, DMSO); limited solubility in nonpolar solvents.
Solubility increases with deprotonation (basic aqueous media) due to carboxylate formation.
Partitioning (literature):
Low to moderate hydrophilicity is typical for N-acetyl amino acids; logP/logD values are expected to be small; exact values Not specified for this item.
Always verify exact physical property values for your lot on the CoA/Spec Sheet before designing quantitative processes.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret common grades (general guidance):
Research/biochemical grade: suitable for general laboratory synthesis and biochemical work; typical controls on inorganic/organic impurities but may not meet chromatographic or GMP criteria.
Peptide-synthesis grade: emphasizes low water content, low residual solvents/metals, and tight controls on enantiomeric excess; often includes HPLC assay and chiral purity reporting.
HPLC grade (for solvents) is not applicable here; however, low-UV-absorbing profiles are valued for analytical uses of amino acid derivatives.
Enantiopurity considerations:
As a D-stereochemical reagent, enantiomeric excess (ee) is critical when used in asymmetric synthesis or chiral resolution work. If ee is not listed, request chiral HPLC data on the CoA.
Stabilizers/Additives:
Not typically required for N-acetyl amino acids; none are specified for this item.
NMR (1H/13C) to confirm N-acetylation and ring integrity
IR to verify amide/carboxyl carbonyls
HPLC/UPLC purity and chiral HPLC for enantiopurity
Water content by Karl Fischer if used in moisture-sensitive couplings
Consult the lot-specific CoA/Spec Sheet for definitive assay, impurities, water, optical rotation, and enantiopurity data.
Reaction and Applications
N-Acetyl-D-Proline is a useful chiral building block and protecting-group derivative of proline. Its blocked amine (amide) and free carboxyl group provide orthogonal reactivity for diverse transformations.
Representative applications (literature/general):
Peptide/fragment coupling: as a D-proline terminus (C-terminal carboxyl activation with EDC/HOBt, HATU, or DIC/DMAP) to couple with nucleophiles (amines, alcohols).
Esterification: formation of methyl/benzyl esters for protection or to tune lipophilicity; Fischer (acid-catalyzed) or Steglich (DCC/DMAP) routes.
Amide bond formation at the carboxyl: mixed anhydrides, acid chlorides (via oxalyl chloride or thionyl chloride) followed by amine coupling to introduce N-acetyl-D-Pro as a chiral auxiliary element in larger amide frameworks.
Resolution/asymmetric induction studies: incorporation of D-proline motif to probe stereochemical outcomes or as part of chiral auxiliaries/ligands.
Cyclization/derivatization at the ring: oxidation at C-5, N–O acyl migrations (under strong activating conditions), or conversion of the carboxylate to activated esters (NHS, pNP) for bioconjugation.
Practical notes:
The amide nitrogen is non-nucleophilic; reactions occur primarily at the carboxyl function or at activated α-positions.
Maintain control of stereochemistry: avoid racemizing conditions (strong base, high temperature during acid chloride formation). Employ mild coupling systems and additives to suppress epimerization.
Water content can inhibit carbodiimide couplings; dry solvents/reagents and monitor by TLC/HPLC.
All examples above are literature-type uses; optimize conditions per substrate set.
Reaction Conditions
Typical conditions for transforming the carboxyl group of N-Acetyl-D-Proline are summarized below as general literature guidance (not item specifications):
Amide bond formation (to amines):
Solvents: DMF, DCM, NMP, or MeCN; reactions often tolerate small amounts of base (DIPEA, NMM).
Activators: EDC (0.9–1.2 eq) with catalytic Oxyma/HOAt analogs; HATU or TBTU (1.0–1.2 eq) for hindered partners; DIC/DMAP for Steglich amidation.
Temperature/time: 0–25 °C for 1–16 h; monitor for completion by TLC/HPLC. Maintain low temperatures during acid chloride formation to suppress racemization.
Esterification:
Fischer: ROH (neat or as solvent) with catalytic strong acid (H2SO4, p-TsOH), 40–70 °C; remove water (Dean–Stark or molecular sieves) to drive conversion.
Steglich: DCC (1.1 eq)/DMAP (0.1 eq) in DCM or THF at 0–25 °C; filter DCU and purify.
Acid chloride route:
Reagents: (COCl)2 or SOCl2 (1.2–2.0 eq) with catalytic DMF, 0–25 °C; brief exposure followed by coupling to nucleophile and base (e.g., pyridine, triethylamine). Use minimal time to limit epimerization.
Activated esters for bioconjugation:
NHS or pNP ester formation using DCC or EDC chemistry; isolate and use promptly to avoid hydrolysis.
Expected yields: Highly substrate-dependent; modest to high isolated yields are common when epimerization is controlled. Always confirm stereochemical integrity (e.g., chiral HPLC, optical rotation).
Safety and Handling
GHS classification and hazard statements: Not specified for this item; consult the SDS for authoritative classification and first-aid measures.
Anticipated hazards (general for small amino acid derivatives): low volatility solid; dust may cause mechanical irritation to eyes/respiratory tract. Avoid inhalation of dust and contact with eyes/skin.
Personal protective equipment (PPE):
Laboratory coat, safety glasses or goggles, and suitable chemical-resistant gloves (e.g., nitrile)
Use a dust mask/respirator if airborne particulate may be generated (per risk assessment)
Handling practices:
Handle in a clean, dry environment. Avoid generating dust. Use local exhaust ventilation when weighing or transferring powders.
Prevent contamination with strong oxidizers and strong bases/acids unless intended for reaction.
Incompatibilities (general): strong oxidizing agents; strong bases/acids may induce salt formation or hydrolysis in extreme conditions.
First-aid overview (general):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin contact: wash with soap and water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention if irritation persists.
Ingestion: rinse mouth; seek medical advice if unwell.
Fire safety: Organic solid; use water spray, dry chemical, CO2, or foam. Combustion may produce CO/CO2 and nitrogen oxides.
Always refer to the product SDS for definitive safety, toxicological, and disposal guidance. For research use only.
Solvent Selection
Because N-Acetyl-D-Proline is a polar, zwitterion-forming carboxylic acid bearing an amide, solvent choice strongly affects dissolution and reactivity.
Polarity/miscibility (literature/general):
Readily soluble in polar protic solvents (water, methanol, ethanol). Soluble in DMF/DMSO. Poorly soluble in nonpolar solvents (hexanes, toluene) unless converted to a salt or ester.
Deprotonation (e.g., with NaHCO3/Na2CO3) increases aqueous solubility via carboxylate formation.
Typical selection by use case:
Analytical sample prep: water, 50:50 water–acetonitrile with 0.1% acid/base modifier as needed; DMSO stock solutions for bioassays.
Coupling/derivatization: DMF, NMP, or DCM/alcohol mixtures with appropriate coupling reagents; methanol/ethanol for esterifications.
Crystallization/purification: water–alcohol mixtures or aqueous buffers adjusted near the isoelectric pH to minimize solubility.
Comparison (general):
Water: green, excellent for salts; may require pH control to dissolve neutral acid.
Methanol/ethanol: good solvency; enable Fischer esterification; flammable.
DMF/DMSO: strong solvency for coupling chemistry; consider toxicity and downstream removal challenges.
Note: Solubility values and exact miscibility limits are not specified for this item. Verify experimentally at your working temperature and pH.
Storage and Reconstitution
Storage conditions (from Product Data):
Store at room temperature. Ship under normal conditions.
General stability guidance (literature/general):
Keep tightly closed in a dry container, protected from excessive humidity and direct light. Avoid prolonged exposure to strong acids/bases unless intended for reaction.
Reconstitution/preparation notes (general):
Aqueous solutions: Prepare with deionized water; adjust pH if needed to aid dissolution (formation of the carboxylate salt increases solubility). Filter through 0.22 µm for analytical or bioassay uses.
Organic solutions: Use fresh, dry solvents (e.g., methanol, ethanol, DMF, DMSO). For moisture-sensitive downstream reactions (e.g., carbodiimide couplings), ensure solvents and glassware are dry.
Recommended storage of solutions: Refrigeration (2–8 °C) for short-term aqueous stocks; freeze aliquots (−20 °C) for longer-term storage to limit hydrolysis—verify stability by HPLC before critical experiments.
Shelf-life: Not specified for this item; refer to CoA/Spec Sheet.
Always consult the lot-specific CoA and SDS for definitive handling, stability, and storage information. For research use only.
Structure and Identity
Brief description: N-Acetyl-D-Proline is the N-acylated derivative of the D-enantiomer of proline, featuring a five‑membered pyrrolidine ring bearing an exocyclic carboxylic acid and an N-acetyl amide.
Item-specific identifiers (from Product Data)
CAS: 59785-68-1
CID: 719436
InChIKey: 106645 (as provided)
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.
Structural features (general/literature description)
Ring system: saturated five-membered pyrrolidine ring (proline core)
Functional groups: secondary amide (N-acetyl), carboxylic acid (α to the ring nitrogen)
Stereochemistry: single stereogenic center at the α-carbon; D-configuration (mirror image of the natural L form)
2D description: a pyrrolidine ring with the ring nitrogen bearing an acetyl group (–COCH3) and the α-carbon bearing –CO2H; the amide carbonyl and carboxylate carbonyl are non-conjugated
Note: Exact identifiers such as SMILES and elemental formula for this item are not specified in the Product Data; consult the CoA/Spec Sheet for definitive values.
Synthetic Utility
N-Acetyl-D-Proline provides a pre-protected proline nitrogen (as an amide) with a reactive carboxylic acid, enabling selective transformations without concerns over amine participation.
Functional group reactivity (literature/general):
Carboxylic acid: activation to acid chlorides, mixed anhydrides, or active esters (NHS, pNP) for coupling to amines/alcohols.
Amide (N-acetyl): stable under many conditions; resists nucleophilic attack; can be retained as a protecting group or strategic polarity modifier.
α-Stereocenter: avoid base/heat-induced epimerization during activation; use mild, fast coupling systems.
Named reaction contexts:
Steglich esterification (DCC/DMAP) to access esters without harsh acid.
EDC/HOBt- or HATU-mediated amidation for peptide linkage formation with preserved stereochemistry.
Mukaiyama-type or mixed anhydride activations for coupling to hindered nucleophiles.
Retrosynthetic value:
Serves as a chiral carboxyl-component fragment where the nitrogen must remain non-nucleophilic.
D-configuration offers access to diastereomeric series complementary to L-proline-based synthons, aiding SAR and chiral recognition studies.
Workup/purification tips:
Use aqueous acid/base toggling to move between neutral and carboxylate forms for phase manipulation.
For peptide-like products, reversed-phase chromatography or crystallization from water–alcohol systems is often effective.
All points are general literature guidance; tailor to your substrates and scale.
Target Specificity
Not applicable. This product is a small-molecule amino acid derivative, not a biological targeting reagent or antibody. No antigen, epitope, clone, isotype, or species reactivity information applies.
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