Trt-D-Dap(Fmoc)-OH - ≥95% , CAS No.1263047-04-6

CAS: 1263047-04-6 Cat. No.: T949441 PubChem CID: 51341717

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)NC(CNC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46)C(=O)O

IUPAC Name

(2R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(tritylamino)propanoic acid

InChIKey

SUDPKNWTNWZJPY-UUWRZZSWSA-N

INCHI

1S/C37H32N2O4/c40-35(41)34(24-38-36(42)43-25-33-31-22-12-10-20-29(31)30-21-11-13-23-32(30)33)39-37(26-14-4-1-5-15-26,27-16-6-2-7-17-27)28-18-8-3-9-19-28/h1-23,33-34,39H,24-25H2,(H,38,42)(H,40,41)/t34-/m1/s1

Isomeri SMILES

C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)N[C@H](CNC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46)C(=O)O

PubChem CID

51341717

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Triphenyl compounds

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Triphenyl compounds
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Triphenyl compounds
• Alternative Parents: Fluorenes D-alpha-amino acids Aralkylamines Benzene and substituted derivatives Carbamate esters Amino acids Monocarboxylic acids and derivatives Dialkylamines Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Triphenyl compound - Fluorene - Alpha-amino acid - Alpha-amino acid or derivatives - D-alpha-amino acid - Aralkylamine - Monocyclic benzene moiety - Carbamic acid ester - Amino acid or derivatives - Amino acid - Secondary amine - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Secondary aliphatic amine - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Amine - Organic oxygen compound - Aromatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as triphenyl compounds. These are aromatic compounds containing a triphenyl moiety.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 568.700 g/mol
• XLogP3: 4.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 568.236 Da
• Monoisotopic Mass: 568.236 Da
• Topological Polar Surface Area: 87.700 Ų
• Heavy Atom Count: 43
• Formal Charge: 0
• Complexity: 839.000
• 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

Not applicable as validated bioassays.

• No WB/IHC/IF/FC protocols apply to this reagent. For practical use, refer instead to the Reaction Conditions and Synthetic Utility sections for SPPS workflows.

Manufacturer Applications (from Product Data)

• Not provided for this item; general application is as an orthogonally protected D-Dap building block for Fmoc-based peptide synthesis.

Biological Roles

Context (general, not product-specific claims)

• 2,3-Diaminopropionic acid (Dap) is a non-proteinogenic amino acid. Its D-enantiomer can modulate peptide conformation and proteolytic stability when incorporated into synthetic peptides.
• Dap residues occur in certain natural products and peptide antibiotics (e.g., as biosynthetic precursors or structural motifs) where the β-amine participates in cross-links or chelation.

Relevance in peptide design

• The side-chain primary amine enables post-synthetic functionalization (e.g., conjugation with acids, isocyanates, aldehydes after deprotection) to create branched architectures or enhance binding interactions.
• Incorporation of D-amino acids can bias local secondary structure, influence receptor selectivity, and reduce enzymatic degradation in biochemical assays.

Biochemical considerations

• Protonation: At physiological pH, unprotected Dap would carry positive charge on the side chain and α-amine; in protected synthetic intermediates like Trt-D-Dap(Fmoc)-OH, these amines are masked until deprotection.
• Stereochemistry: D-configuration may alter chiral recognition in enzyme binding or transport, which is leveraged to probe structure–activity relationships in research.

Note

• This product is supplied for research use only and is intended as a synthetic building block; it is not used directly in biological systems without deprotection and incorporation into designed molecules.

Buffer Applications

Not typically applicable.

• Trt-D-Dap(Fmoc)-OH is a protected amino acid building block and is not used to prepare aqueous buffer systems. Its poor aqueous solubility and protected amines preclude buffering action.
• For practical guidance, see Reaction & Applications, Synthetic Utility, and Reaction Conditions for its role in peptide synthesis.

Green Alternatives

Greener processing considerations (general)

• The main sustainability impact arises from the solvent and coupling reagent choices in SPPS rather than from the protected amino acid itself.

Potential substitutions and trade-offs (literature)

• Solvents
  • Replace DMF/NMP with N-butylpyrrolidone (NBP), PolarClean (N,N-dimethyl-5-decanamide), or Cyrene where solubility and resin swelling are adequate. Validation is sequence-dependent.
  • Use EtOAc or CPME for wash steps in place of DCM when compatible with resin and reagents.
• Coupling reagents/additives
  • Oxyma Pure with DIC can reduce hazardous energetic additives vs. HOBt/HOAt; COMU offers high efficiency with reduced byproduct concerns compared to HBTU/HATU.
• Process
  • Implement flow or microwave-assisted SPPS to reduce reaction time and solvent usage; employ solvent recirculation and in-line filtration.

Concise comparison (general)

• DMF/NMP: Benchmark performance; environmental and regulatory concerns.
• NBP/PolarClean: Improved EHS profiles; may require longer times or elevated temperatures to match conversions.
• DCM vs. EtOAc/CPME: EtOAc/CPME are less halogenated-waste intensive but may affect resin swelling and selectivity for Trt manipulations.

Recommendation

• Start with mixed-solvent screens (e.g., NBP:DMF 1:1) to verify dissolution of Trt-D-Dap(Fmoc)-OH and coupling efficiency; document any impact on deprotection selectivity.

Pharmaceutical Uses

Formulation/context (general, no therapeutic claims)

• Role: Chiral building block for the synthesis of peptide intermediates and APIs via SPPS or solution-phase assembly. The orthogonal protection scheme facilitates complex side-chain architectures.
• Regulatory aspects: When such building blocks are used in GMP settings, typical documentation includes CoA, TSE/BSE statements, residual solvent profiles, and enantiomeric purity data. This listing does not specify any pharmacopeial monograph.
• Process utility: Trt group offers acid-labile protection compatible with Fmoc chemistry, enabling streamlined global deprotection/cleavage with TFA cocktails; Fmoc allows base-triggered cycles without affecting Trt.

Manufacturing considerations

• Impurities control: Monitor for partially deprotected species, racemization byproducts, and residual coupling reagents to ensure downstream purity.
• Analytical support: RP-HPLC with UV detection at 210/254/301 nm (Fmoc absorbance) is commonly used; identity confirmation by NMR and HRMS is standard in GMP settings.

Note

• No excipient role is intended; this product is for research and manufacturing use as a reagent/intermediate only.

Physical Properties

Item-specific (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for Fmoc/Trt-protected amino acids (non-specification)

• Physical state: Typically a white to off-white crystalline solid or foam, depending on crystallization and solvation; hygroscopicity is generally low-to-moderate.
• Solubility: Good solubility in polar aprotic organic solvents commonly used for SPPS, such as DMF, NMP, DCM, and acetonitrile. Limited solubility in protic solvents and water; insoluble in hydrocarbons.
• Acid/base behavior: Free carboxylic acid (pKa of analogous Fmoc-AA acids ~3–4, literature), two amines masked as Fmoc-carbamate (base-labile) and Trt-ammonium-like (acid-labile). No free amine under neutral conditions.
• Partitioning: Fmoc and Trt groups markedly increase hydrophobicity vs. unprotected Dap; expect strong retention on RP-HPLC.
• Melting behavior: Many Fmoc-protected amino acids decompose or foam near melting; exact MP for this item is not specified.
• UV characteristics (literature): Fmoc chromophore exhibits strong absorbance around 260–300 nm (ε varies with medium), enabling UV monitoring of deprotection; Trt also absorbs in the UV. Exact cutoffs for this item are not specified.

Note: Do not treat the above as product specifications; consult the CoA/SDS for authoritative physical data.

Quality and Grades

Item-specific (from Product Data)

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

Context for peptide synthesis materials (general)

• Peptide (SPPS) grade: Typically implies high chemical purity, low levels of inorganic salts, and suitability for solid-phase protocols with minimized side-products (e.g., low residual solvents and controlled levels of related substances). UV transparency is less critical than for HPLC-grade solvents but batch-to-batch consistency is key.
• Chiral purity: For D-amino acid derivatives, enantiomeric excess is often specified in high-quality products to prevent epimerization issues; when not listed, verify by CoA/chiral HPLC.
• Protecting group integrity: Confirm by NMR/UPLC that the Fmoc and Trt loadings are intact; absence of partially deprotected species is important for reproducible couplings.
• Water content: Karl Fischer limits can affect resin swelling and coupling; exact specification for this item is not provided and should be checked on the CoA.
• Trace amines/acids: Residual piperidine or TFA from handling can catalyze undesired deprotection; high-grade materials control these to very low levels.

Recommendation

• For regulated or critical syntheses, request CoA with assay, chromatographic purity profile, residual solvent panel, and enantiomeric purity. Conduct a small pilot coupling to benchmark performance before scale-up.

Reaction and Applications

Use case overview

• Trt-D-Dap(Fmoc)-OH is designed for Fmoc-based SPPS to introduce D-2,3-diaminopropionic acid with orthogonal protection: Fmoc on the α-amine (base-labile) and Trt on the β-amine (acid-labile). This enables stepwise assembly with later selective side-chain deprotection.

Typical applications (general/literature)

• Incorporation of D-residues to modulate peptide backbone conformation, protease resistance, and β-turn preferences.
• Preparation of branched or side-chain-extended motifs by post-assembly transformation at the β-amine after Trt removal.
• Cyclization strategies: On-resin or solution-phase lactam formation between β-NH2 and acidic partners, creating constrained scaffolds.
• Mimicry of diaminobutyric/ornithine topologies via homologation from Dap.

Orthogonality and deprotection

• Fmoc removal: 20% piperidine in DMF (or 2% DBU/2% piperidine) at RT, short cycles, while Trt remains intact under these basic conditions.
• Trt removal: TFA-based cocktails (e.g., 1–5% TFA in DCM for selective side-chain detritylation on resin; higher TFA for global deprotection). Optimize to avoid premature cleavage from acid-labile resins.

Practical considerations

• Coupling: Use HATU/HBTU/COMU or DIC/Oxyma. For hindered sequences, double coupling or mild heating (≤50 °C) can improve conversion.
• Racemization: D-configuration at the α-carbon should be preserved under standard Fmoc conditions; minimize prolonged base exposure.
• Analysis: Monitor Fmoc deprotection by UV (dibenzofulvene adduct) and check on-resin tests (e.g., Kaiser or Chloranil, accounting for protected side-chain amine).

Reaction Conditions

General SPPS conditions (literature guidance; not product specifications)

• Dissolution: 0.1–0.2 M in DMF or NMP; sonication or slight warming may assist. Filter through 0.2 µm PTFE.
• Coupling reagents: HATU/HBTU/COMU (3–4 equiv relative to resin loading) with DIEA (6–8 equiv); or DIC (3–4 equiv) with Oxyma (3–4 equiv). Typical contact time 10–60 min at RT; consider double coupling for difficult sequences.
• Fmoc deprotection: 20% piperidine in DMF, 2 × 5–10 min at RT; alternatives include 2% DBU/2% piperidine for reduced diketopiperazine formation on sensitive dipeptides.
• Trt deprotection (selective, on-resin): 1–5% TFA in DCM with scavengers (e.g., triisopropylsilane, water) for short cycles; monitor with on-resin tests. Global Trt removal occurs during final cleavage with higher TFA concentrations.
• Temperature: Ambient for most steps; up to 50 °C (microwave or heated SPPS) can accelerate coupling—verify stability of protecting groups and resin.
• Workup/cleavage: Standard TFA cocktails (e.g., 95% TFA with scavengers) effect global deprotection/cleavage from acid-labile resins; optimize to avoid side reactions of liberated β-amine.

Analytical monitoring

• Kaiser/Chloranil tests guided by protecting group state; UV monitoring of Fmoc removal by dibenzofulvene adduct at ~301 nm (literature).

Note: Adjust equivalents and times to resin loading, sequence context, and equipment (manual vs. automated synthesizer).

Safety and Handling

Item-specific (from Product Data)

• GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.
• Storage conditions: Room temperature.

General safety guidance (defer to SDS for authoritative instructions)

• Likely hazards: Fmoc/Trt-protected amino acids are typically classified as irritants; avoid inhalation of dust and contact with skin/eyes.
• PPE: Lab coat, safety glasses, and suitable gloves (e.g., nitrile). Handle powders in a fume hood or ventilated enclosure to minimize dust exposure.
• Incompatibilities: Strong bases (e.g., piperidine) remove Fmoc; strong acids (e.g., TFA) remove Trt. Avoid unintended exposure to these reagents outside planned procedures. Oxidizing agents and strong reducing agents may be incompatible with the aromatic protecting groups.
• First aid (general): If on skin/eyes, rinse with water for ≥15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical attention. Always follow institutional protocols.
• Spill response: Avoid raising dust, collect mechanically or with damp disposable towels/HEPA vacuum. Dispose according to local regulations.
• Thermal/photostability: Protect from prolonged heat and strong acids/bases. Store dry, tightly closed, and protected from excessive light to preserve Fmoc integrity.

Note: Always consult the SDS for this specific SKU for definitive hazard classification and response measures.

Solvent Selection

Applicability

• This product is a protected amino acid building block, not itself used as a reaction solvent. Selection below is for dissolving/processing in peptide synthesis.

General guidance (literature/practice)

• Primary dissolution solvents: DMF and NMP provide excellent solubility and resin swelling; DCM is useful for washes and for Trt-related manipulations but may require co-solvent with DMF for complete dissolution.
• Alternative/greener options: Dimethyl sulfone-bearing solvents and newer dipolar aprotics (e.g., NBP, PolarClean) can sometimes substitute for DMF/NMP; verify solubility case-by-case.
• Aqueous media: Poorly soluble; avoid water except during final peptide workups or when formulating coupling solutions that are anhydrous.
• Additives: Bases (DIEA) are used during coupling; ensure solutions are freshly prepared to avoid premature Fmoc loss in strongly basic mixes.

Comparison snapshot (general)

• DMF: High solvency, standard for SPPS; toxicity concerns, but predictable performance.
• NMP: Similar to DMF; higher boiling point; regulatory scrutiny in some regions.
• DCM: Excellent for washes and side-chain protecting group manipulations; limited polarity for some operations; volatile.
• ACN: Useful for HPLC prep and some solution-phase couplings; may require small amounts of DMF to boost solubility.

Tip

• Filter solutions (0.2 µm PTFE) before charging to automated synthesizers to prevent line clogging; verify compatibility of tubing with chosen solvent.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General handling and reconstitution (guidance)

• Storage: Keep tightly closed in a dry, inert atmosphere (desiccator with desiccant). Protect from prolonged exposure to strong light, acids, and bases to preserve protecting groups. If long-term storage is planned, consider refrigeration (2–8 °C) as a precaution—allow to equilibrate to room temperature before opening to avoid condensation.
• Reconstitution: Dissolve in anhydrous DMF or NMP to prepare 0.1–0.2 M stock solutions for SPPS. For solution-phase work, DCM or ACN may be used, often with a small fraction of DMF to improve solubility. Filter through 0.2 µm PTFE before use.
• Stability in solution: Prepare fresh solutions on the day of use, especially when bases (e.g., DIEA) are present, to minimize premature deprotection or side reactions.
• Freeze–thaw: For solid material, not applicable. If stock solutions are stored short-term at 2–8 °C, minimize freeze–thaw cycles and protect from moisture.

Research use note

• For research use only. Not for diagnostic or therapeutic use.

Structure and Identity

Brief description: Trt-D-Dap(Fmoc)-OH is an orthogonally protected D-2,3-diaminopropionic acid (D-Dap) building block for peptide synthesis, bearing an Fmoc group on the α-amine and a trityl (Trt) group on the side-chain amine.

Item-specific (from Product Data)

• SKU: T949441
• Product name: Trt-D-Dap(Fmoc)-OH
• CAS: 1263047-04-6
• InChIKey: 345481 (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)

• Core scaffold: D-2,3-diaminopropionic acid (D-Dap), an α-amino acid with a β-amine side chain and a terminal carboxylic acid.
• Protecting groups: Fmoc (9-fluorenylmethoxycarbonyl) on the α-NH2 (base-labile); Trityl (triphenylmethyl, Trt) on the β-NH2 (acid-labile).
• Functional groups: Secondary carbamate (Fmoc), benzylic tertiary ether-like C–N protection in Trt, carboxylic acid, and protected primary amines.
• Stereochemistry: D-configuration at the α-carbon (inverted relative to L-amino acids commonly used in ribosomal peptides).

2D structure in words (general)

• A three-carbon backbone bearing: C1 carboxylate (CO2H), C2 chiral center carrying Fmoc-protected α-amine and H, and C3 bearing a Trt-protected primary amine (–CH2–NH–Trt). The Fmoc group is a fluorenyl ring system linked via a carbamate to the α-nitrogen; the Trt group is a triphenylmethyl substituent bound to the β-nitrogen.

Synthetic Utility

Orthogonal protection logic

• α-NH2 protected with Fmoc (base-labile), β-NH2 protected with Trt (acid-labile), CO2H free. This configuration enables straightforward SPPS elongation at the α-terminus while preserving the side-chain amine for later transformations.

Transformations enabled (general)

• On-resin side-chain chemistry: After selective Trt removal (mild TFA/DCM), the β-amine can undergo acylation, sulfonylation, urea/thiourea formation, reductive alkylation, or ring closure to form lactams.
• Macrocyclization: β-NH2 can participate in head-to-side-chain or side-chain-to-side-chain cyclizations, stabilizing bioactive conformations.
• Branching: Introduction of Lys-like branching points or dendrons by sequential acylations at the β-amine.
• Chemoselective ligations: Post-cleavage modification via NHS esters, isocyanates, or aldehydes (NaBH3CN reductive amination) after global deprotection.

Retrosynthetic value

• Access to diaminated motifs without resorting to orthogonal protecting group juggle mid-sequence. D-stereochemistry offers access to mirror-image scaffolds for D-peptide design and protease resistance studies.

Practical notes

• Avoid prolonged base exposure during Fmoc deprotection to minimize any risk of epimerization; fast cycles and room temperature are generally sufficient.
• Use excess coupling reagent or double coupling for hindered sequences; cap residual amines to prevent deletion sequences.

Target Specificity

Not applicable.

• This product is a small-molecule peptide building block and does not have biological target specificity like an antibody or inhibitor. No antigen/epitope or isotype information applies.

Domande frequenti

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

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

The CAS Number is 1263047-04-6. InChIKey SUDPKNWTNWZJPY-UUWRZZSWSA-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.