Boc-L-Valine-d - ≥99% , CAS No.153568-33-3

CAS: 153568-33-3 Cat. No.: B1454126 Formula: C₁₀H₁₁D₈NO₄ Peso molecolare: 225.31

GRADE & PURITY ≥99%

Storage

Store at 2-8°C

Shipped In

Wet ice

Panoramica

Boc-L-Valine-d 8 is the deuterium labeled Boc-L-Valine.

Specifications

Specifiche e purezza

≥99%

Condizioni di conservazione di stoccaggio

Store at 2-8°C

Spedito in

Wet ice

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Purezza

≥99%

Nomi e identificatori

Peso molecolare

225.31

Application Protocols

No assay application protocols (e.g., WB, IHC, IF, FC) apply to this small-molecule building block.

General usage examples (literature)

• Solution-phase coupling: Dissolve Boc-L-valine derivative and amine partner in dry DMF; add Oxyma and DIC at 0°C; stir and monitor by LC-MS; quench and purify.
• Boc deprotection: Cool to 0°C, add TFA/DCM (1:1); stir 30–60 min; evaporate TFA/DCM under reduced pressure; neutralize and proceed to next coupling.

Refer to peer-reviewed procedures and adjust stoichiometry and conditions for your specific substrate.

Biological Roles

• Item-specific biological activity: This is a protected, synthetic derivative intended for chemical synthesis; no direct biological role is claimed for the protected form. For research use only.

• General context (literature)

  • Valine is one of the three branched-chain essential amino acids (BCAAs) incorporated into proteins and involved in energy metabolism via transamination to ketoacids and subsequent entry into central metabolic pathways.
  • Protecting the α-amino group as Boc renders the molecule non-proteinogenic and not a substrate for ribosomal protein synthesis.
  • The Boc group serves purely synthetic purposes—controlling chemoselectivity during assembly of peptides and peptidomimetics.

• Practical implication

  • Any biological assays should be conducted on the deprotected amino acid or final target molecule; the Boc-protected precursor is generally not biologically active and may be poorly soluble in aqueous buffers.

Buffer Applications

Not typically applicable. Boc-protected amino acids are hydrophobic building blocks and are not used as buffering agents. For aqueous work, buffers would be applied to the final, deprotected peptide or amino acid product rather than to the Boc-protected precursor.

Green Alternatives

• Greener solvent choices (general)

  • Replace DCM with 2-MeTHF, CPME, or EtOAc where solubility and coupling efficiency allow.
  • Use Me-THF or EtOAc for extractions instead of chlorinated solvents.

• Alternative coupling reagents (EHS considerations)

  • Favor Oxyma/EDC systems to reduce formation of hazardous benzotriazole-derived wastes (vs HOAt/HOBt). OxymaPure with DIC is a common, lower-sensitization alternative to uronium salts.
  • Water- or EtOAc-based couplings can be explored with phase-transfer catalysis or micellar media for certain substrates.

• Trade-offs

  • Solubility of Boc-amino acids may limit use of greener, less polar solvents; co-solvent strategies (EtOAc/EtOH, 2-MeTHF/DMF) can help.
  • Reaction rates in greener media may be slower; temperature elevation must be balanced against epimerization risk.

Comparison snapshot (general)

• DCM: Excellent solubility, easy removal; environmental concerns and halogenated waste.
• 2-MeTHF: Renewable feedstock, good partitioning; water content control needed, may require drying.
• EtOAc: Low toxicity, biodegradable; may need larger volumes for complete dissolution.
• CPME: Broad azeotrope profile, low peroxide tendency; sometimes limited availability/cost.

Pharmaceutical Uses

• Use class: Synthetic intermediate/building block.
• Pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet if relevant.

General formulation/manufacturing context (no therapeutic claims)

• Boc-L-valine derivatives may be employed in the convergent synthesis of drug substance intermediates, peptidomimetics, and prodrugs where incorporation of L-valine stereochemistry is desired.
• Benefits of Boc protection in process chemistry include improved crystallinity/handling, phase behavior favorable to purifications, and orthogonal deprotection relative to base-labile groups elsewhere in the molecule.
• Residual reagent and solvent control: When used in GMP or pilot settings, monitor for carbodiimide-derived ureas, residual coupling reagents (e.g., uronium salts), and chlorinated solvent residues if used.
• Chiral control: Maintain and document optical purity; implement in-process controls to detect epimerization during couplings or acid chloride formation.

Physical Properties

Item-specific physical data

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Other specifications (water content, metal content, residual solvents, UV cutoffs, etc.): Not specified for this item; refer to CoA/Spec Sheet.

General/literature characteristics for Boc-protected amino acids (informational)

• State: Typically a crystalline solid or white/off-white powder.
• Solubility profile (literature, qualitative):
  • Sparingly soluble in water due to hydrophobic Boc and isopropyl side chain.
  • Soluble in common organic solvents used for peptide coupling and workup: dichloromethane (DCM), ethyl acetate, acetonitrile, THF, dioxane, DMF, and DMSO; moderate in alcohols (MeOH, EtOH).
• Acid/base behavior (literature): Free carboxylic acid (pKa of analogous α-CO2H typically ~2–3) and Boc-carbamate nitrogen (non-basic when Boc-protected). Exact pKa values for this specific derivative are not provided here.
• Partitioning (qualitative): Increased lipophilicity vs. unprotected valine due to Boc.

Notes

• Do not treat the above as item specifications. For exact physical constants of this catalog item, consult the CoA/Spec Sheet.

Quality and Grades

• Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet for assay, residual solvents, and impurity profiles.

• How to interpret typical quality information for Boc-protected amino acids (general guidance)

  • Chemical purity: High chemical purity helps suppress side reactions (e.g., epimerization, over-acylation) during peptide couplings. Look for HPLC assay and chiral purity where available.
  • Chiral integrity: For L-α-amino acids, low D-epimer content is important; suppliers may report % ee or % de. Verify on CoA.
  • Water and inorganic salts: Low moisture content benefits solution stability and accurate stoichiometry in coupling reactions.
  • Residual solvents and volatile impurities: Critical for scale-up and regulatory documentation in process chemistry.
  • Stabilizers: Boc-amino acids typically do not require stabilizers; none are specified for this item.

• Practical notes

  • If using in SPPS or sensitive couplings, request/consult the Spec Sheet for optical purity, assay, and relevant chromatographic data (UV trace, HPLC method).
  • For regulatory or GMP-adjacent workflows, ensure lot-specific CoA matches your internal acceptance criteria.

Reaction and Applications

• Primary role: Boc-L-valine derivatives are standard building blocks in peptide synthesis and fragment coupling for small-molecule and peptidomimetic programs.

• Common applications (literature/general)

  • Peptide bond formation: Activation of the carboxylic acid (e.g., with HATU, HBTU, DIC/Oxyma, EDCI) and coupling to amines on resins (SPPS) or in solution.
  • Fragment assembly: Convergent coupling of protected di-/tripeptides where Boc-valine serves as a C-terminal acid component.
  • Protecting-group strategy: Boc is acid-labile; enables orthogonality with base-labile Fmoc on other fragments.
  • Chiral auxiliary/source: Preserves L-configuration, delivering the valine stereochemical information into targets.

• Practical tips

  • Minimize racemization: Use OxymaPure or HOAt analogs; maintain low temperatures during activation; avoid prolonged pre-activation, especially with carbodiimides.
  • Base selection: DIPEA, NMM, or collidine are typical; avoid strong base and heat which can epimerize the α-center.
  • Boc removal: TFA (typically 20–95% in DCM or neat) at 0–25°C; include scavengers if cationic or carbocation-sensitive motifs are present.
  • Purification: Exploit differential solubility; trituration or crystallization can remove urea byproducts from carbodiimide couplings.

• Downstream transformations

  • Conversion to acid chlorides/mixed anhydrides for difficult couplings (with care to reduce racemization).
  • Esterification to enable phase-switch strategies; later hydrolysis regenerates the acid.

Reaction Conditions

General, literature-based guidance (not item specifications)

• Carbodiimide/Oxyma coupling

  • Typical solvents: DMF, NMP, DCM, or mixtures.
  • Bases: DIPEA (2–4 equiv) or NMM (2–3 equiv).
  • Additives: OxymaPure (1.0–1.2 equiv) with DIC (1.0–1.2 equiv) to reduce racemization.
  • Temperature: 0–25°C; maintaining ≤0–5°C during pre-activation minimizes epimerization.
  • Time: 0.5–4 h for small-molecule amines; longer for hindered substrates.

• Uronium salt coupling (HATU/HBTU)

  • Solvent: DMF or NMP.
  • Base: DIPEA (2–4 equiv).
  • Temperature: 0–25°C.
  • Time: 0.5–2 h typical; monitor by LC.

• Mixed anhydride route

  • Reagents: iBuOCOCl (1.1 equiv), NMM (2.0 equiv) at −20 to 0°C; then add amine nucleophile.
  • Advantage: Often lower racemization with hindered amino acids like valine.

• Boc deprotection

  • Reagent: TFA (20–100%), often in DCM; 0–25°C.
  • Time: 0.25–2 h depending on substrate.
  • Scavengers: Anisole, TIPS, water as appropriate.

Note: Optimize equivalents and times for your substrate. Validate absence of epimerization by chiral HPLC or derivatization assays.

Safety and Handling

Authoritative safety details must be taken from the product SDS.

• GHS information (item-specific)

  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification and pictograms: Not specified for this item; refer to SDS.

• General handling guidance (for Boc-protected amino acids; informational)

  • PPE: Use appropriate laboratory PPE—lab coat, safety glasses, and suitable gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust inhalation.
  • Incompatibilities: Avoid strong bases at elevated temperature (risk of racemization), strong oxidizers, and prolonged exposure to acids other than when intentionally performing Boc deprotection (e.g., TFA).
  • Hygroscopicity: Many amino-acid derivatives can absorb moisture; keep containers tightly closed and minimize exposure to ambient humidity.
  • First aid overview: If inhaled—move to fresh air; if on skin/eyes—rinse with water; if ingested—rinse mouth. Seek medical attention in all cases. Follow SDS instructions.
  • Spill response: Avoid dust formation; collect mechanically and dispose according to institutional and local regulations.

• Storage and shipping (item-specific)

  • Storage: Store at 2–8°C (per Product Data).
  • Shipping: Shipped on wet ice (per Product Data).

Solvent Selection

This product is a protected amino acid used as a building block rather than a solvent.

• Practical solvent choices for use (general/literature)

  • Coupling media: DMF, NMP, or DCM are common. Greener alternatives include 2-MeTHF or EtOAc for certain couplings with soluble additives.
  • Workup/extraction: EtOAc/hexanes/brine systems often provide good phase behavior; IPA or MeOH can be used for trituration or crystallization depending on polarity.
  • Boc deprotection: TFA in DCM or neat TFA is standard; scavengers (e.g., anisole, triisopropylsilane) may be added depending on downstream needs.

• Miscibility and polarity (qualitative)

  • The compound is more lipophilic than unprotected valine; expect good solubility in moderately polar aprotic solvents and chlorinated solvents; limited water solubility.

• Selection tips

  • Choose DMF/DMSO for maximum solubility in coupling; switch to less polar media for purification.
  • For greener processing, trial EtOAc or 2-MeTHF with modern coupling systems if solubility permits.

Storage and Reconstitution

• Item-specific storage

  • Store at 2–8°C (per Product Data).
  • Shipped on wet ice to maintain recommended temperature during transit.
  • Keep container tightly closed; protect from moisture and prolonged exposure to acids or bases.

• Reconstitution/handling (general)

  • For solution preparation, use dry, oxygen- and moisture-free solvents when performing air-/moisture-sensitive steps (e.g., couplings).
  • Typical solvents for stock solutions: DMF, DMSO, DCM, or MeCN depending on the intended application. Filter if particulates are present.
  • If weighing fine powders, work quickly and in low humidity; record net mass promptly to minimize error from moisture uptake.

• Stability notes (general)

  • Boc-protected amino acids are generally stable at 2–8°C under inert atmosphere and dry conditions. Avoid prolonged exposure to TFA or other strong acids unless deprotection is intended.

• Research use only

  • For research use only (per Product Data). Not for human or veterinary use.

Structure and Identity

Brief description: Boc-L-Valine-d is an N-tert-butyloxycarbonyl (Boc) protected L-valine derivative, supplied for research use as an amino-acid building block.

• Item-specific identifiers (from Product Data)

  • SKU: B1454126
  • Product name: Boc-L-Valine-d
  • CAS: 153568-33-3
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general/literature description)

  • Core scaffold: L-valine backbone with a chiral α-carbon in the L-configuration.
  • Functional groups: Primary α-amino protected as a tert-butyloxycarbonyl carbamate (Boc); free α-carboxylic acid (–CO2H); branched isopropyl side chain characteristic of valine.
  • Protecting-group logic: Boc group provides acid-labile protection compatible with base-mediated couplings and Fmoc strategies (as a solution-phase fragment) and is typically removed with TFA.
  • Stereochemistry: Single stereocenter at the α-carbon; L-configuration (S absolute configuration by CIP for valine). If isotopic labeling is implied by “-d,” specific labeling sites are not provided in the Product Data; confirm on the CoA.

• 2D structure in words (general)

  • A central chiral carbon bearing: (1) a carboxyl group, (2) a Boc-protected amino substituent (–NH–CO–O–tBu), (3) a methyl-substituted methine leading to an isopropyl side chain, and (4) a hydrogen.

Synthetic Utility

Key functional elements and reactivity (general)

• Carboxylic acid handle: Amenable to activation (mixed anhydrides, acid chlorides) or in situ coupling with carbodiimides/uroniums.
• Boc-protected amine: Stable to bases and many nucleophiles; selectively removed under acid (e.g., TFA) without affecting many base-labile groups.
• Stereocenter at α-carbon: Requires conditions that suppress racemization during activation and coupling.

Named/typical transformations

• Peptide couplings: HATU/HBTU/EDCI or DIC plus Oxyma/HOAt; DIPEA or NMM as base.
• Esterification: Fischer or Steglich esterification to tune solubility or enable protecting-group maneuvers.
• Boc deprotection: TFA/DCM or neat TFA at 0–25°C; subsequent neutralization and scavenging for clean amine liberation.
• Mixed anhydride methods: Isobutyl chloroformate/NMM at low temperature to minimize epimerization, then amine trapping.

Retrosynthetic value

• Serves as a chiral, masked amine synthon delivering the L-valine fragment into targets with minimal protecting-group interference. Compatible with orthogonal schemes (e.g., pairing with Fmoc on other fragments or side-chain protections as needed).

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity reagent. No target, antigen, or isotype information applies.