D-Valine - Moligand™, 10 mM in Water , CAS No.640-68-6

CAS: 640-68-6 Cat. No.: D1499808 分子式: C₅H₁₁NO₂ 分子量: 117.15 Beilstein Registry Number: 1721135 EC番号: 211-368-9

GRADE & PURITY Moligand™, 10 mM in Water

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

概要

D-Valine is the enantiomer of L-Valine. L-Valine is one of 20 proteinogenic amino acids . L-Valine is an essential amino acid.

Specifications

仕様と純度

Moligand™, 10 mM in Water

保管条件

Store at -80°C

入荷

Dry ice packs + Cold packs

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

等級

Moligand™

名前と識別子

• 異性体SMILES: CC(C)[C@H](C(=O)O)N
• WGKドイツ: 3
• RTECS: YV9360000
• 分子量: 117.15
• Beilstein: 1721135
• Reaxy-Rn: 506689
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=506689&ln=

化学的性質と物理的性質

• 比旋光度［α］: -27 ° (C=8, 6mol/L HCl)
• 融点（°C）: 302-303°C

参考文献

1. Zhiyang Xu, Yinzhou Yan, Xingyuan Wang, Xiaolei Wang, Zhixiang Zhou, Xi Yang, Tianrui Zhai.  (2023)  Determination of Enantiomeric Excess by Optofluidic Microlaser near Exceptional Point.  Advanced Science,      [PMID:38072636] [10.1002/advs.202308362]

2. Dan Zhao, Jingjing Huang, Juan Li, Xiao Ma, Fang Wang, Honglei Zhang, Jiaze Xie, Jian Sun, Chuanxia Chen.  (2023)  Ultrasensitive colorimetric and fluorescent dual-readout assay for D-penicillamine based on the chloride boosted oxidative ability of copper ions.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2023.108535]

3. Li Gao, Piao Xu, Jiaoyan Ren.  (2023)  A sensitive and economical method for simultaneous determination of D/L- amino acids profile in foods by HPLC-UV: Application in fermented and unfermented foods discrimination.  FOOD CHEMISTRY,      [PMID:36628920] [10.1016/j.foodchem.2022.135382]

4. Shutong Yang, Liancheng Gu, Fangling Wu, Xinhua Dai, Fuxing Xu, Qiaoyu Li, Xiang Fang, Shaoning Yu, Chuan-Fan Ding.  (2022)  The chirality determination of amino acids by forming complexes with cyclodextrins and metal ions using ion mobility spectrometry, and a DFT calculation.  TALANTA,      [PMID:35272154] [10.1016/j.talanta.2022.123363]

5. Jun Zhang, Tingyang Xing, Min Zhang, Yunlong Zhou.  (2022)  Facile preparation of Cu2-xS supernanoparticles with an unambiguous SERS enhancement mechanism.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2021.134457]

6. Deng Jun, Wu Sai, Yao Mengyun, Gao Changyou.  (2016)  Surface-anchored poly(acryloyl-L(D)-valine) with enhanced chirality-selective effect on cellular uptake of gold nanoparticles.  Scientific Reports,  6  (1): (1-12).  [PMID:27531648] [10.1038/srep31595]

7. Jun Zhang, Kai Wu, Xiaoqing Gao, Min Zhang, Xin Zhou, Florian Bertram, Chen Shen, Yunlong Zhou.  (2024)  Achiral and chiral ligands synergistically harness chiral self-assembly of inorganics.  Science Advances,  10  (42):   [PMID:39423258] [10.1126/sciadv.ado5948]

8. Ding Junfeng, Wang Tianran, Lin Zhiqiang, Li Zhenyu, Yang Jiaxuan, Li Fujiang, Rong Yan, Chen Xuesi, He Chaoliang.  (2025)  Chiral polypeptide hydrogels regulating local immune microenvironment and anti-tumor immune response.  Nature Communications,  16  (1): (1-21).  [PMID:39890820] [10.1038/s41467-025-56137-w]

9. Lilan Tan, Wenrong Cai, Fangqin Wang, Junyao Li, Datong Wu, Yong Kong.  (2024)  Postsynthetic Modification Strategy for Constructing Electrochemiluminescence-Active Chiral Covalent Organic Frameworks Performing Efficient Enantioselective Sensing.  ANALYTICAL CHEMISTRY,      [PMID:38394220] [10.1021/acs.analchem.3c05887]

10. Zhou Mengyan, Zhang Zhihui, Zheng Qi, Yu Mingdi, Si Mengxu, Wu Sirui, Zhang Yanan, Ding Shushu, Fu Ding-Yi.  (2025)  Ratiometric fluorescence quantification of folic acid utilizing D-penicillamine-based carbon dots in conjunction with glutathione S-transferase-Au nanoclusters.  MICROCHIMICA ACTA,  192  (4): (1-13).  [PMID:40080078] [10.1007/s00604-025-07062-8]

11. Simin Zhang, Xiangfeng Chen, Yaping Shi, Xiangyu Zhu, Zongwei Cai.  (2026)  Soft-Chain-Induced Ultrahigh-Resolution Chiral Separation of Amino Acids via Bimetallic Immobilization in MALDI-TIMS-MS.  ANALYTICAL CHEMISTRY,      [PMID:41701523] [10.1021/acs.analchem.5c07869]

Application Protocols

No vendor-tested biological assay protocols are specified for this item. Typical laboratory uses are synthetic (e.g., peptide coupling after protection) or analytical (e.g., chiral standard preparation). For biochemical applications, users generally:

• Prepare aqueous stock solutions (50–200 mM) by pH-adjusted dissolution (acidic or basic) and sterile filtration if needed (general guidance).
• Validate concentration by quantitative NMR or amino acid analysis if required.

Item-specific validated protocols and recommended dilutions: Not specified for this item; refer to CoA/Spec Sheet or develop method-specific SOPs.

Biological Roles

General literature information (not item-specific, no clinical claims):

• Stereochemistry in biology:
  • L‑valine is one of the 20 proteinogenic amino acids in ribosomal proteins. D‑valine, the enantiomer, is uncommon in higher eukaryotes but occurs in bacterial peptidoglycan and in certain non‑ribosomal peptides and lipopeptides, where D‑residues influence conformation, stability, and biological recognition.
• Metabolic context:
  • Branched-chain amino acids (BCAAs) undergo transamination (branched-chain aminotransferase) and oxidative decarboxylation (BCKDH complex) in L‑form pathways. D‑valine can be interconverted with L‑valine by amino acid racemases in microorganisms (e.g., alanine/valine racemases) and may act as a probe for stereoselective transporters/enzymes in vitro.
• Structural/biophysical aspects:
  • The isopropyl side chain is hydrophobic and β‑branched, promoting β‑sheet formation and influencing peptide secondary structure. Introducing a D‑residue can disrupt or reconfigure local secondary structure, aiding conformational studies and protease resistance (general phenomenon).
• Analytical/assay relevance:
  • D‑valine standards are used to calibrate chiral LC/MS methods for D/L amino acid profiling in microbiology and metabolomics. They also assist in characterizing racemase specificity and kinetics.

These roles inform typical research uses of D‑valine as a stereochemical control, enzyme substrate/standard, and a module for tuning peptide properties.

Buffer Applications

D‑Valine is not a conventional buffering reagent. Its acid/base centers (pKa ~2.3 and ~9.6; literature) are far apart, and the zwitterionic species predominates near pI (~6.0), yielding weak buffering capacity compared with dedicated Good’s buffers.

• When it may be used (general):
  • As an additive or component in specialized media or assay solutions to probe transporter specificity or enzyme stereoselectivity, not primarily for buffering.
  • Temporary pH control is possible in the vicinity of each pKa, but capacity is low and composition-dependent.
• Practical guidance:
  • For robust buffering at neutral pH, prefer HEPES, MOPS, or phosphate. For acidic or basic ranges, choose citrate/acetate or Tris/AMPD respectively.
  • If using D‑valine in solution, adjust pH with dilute acid/base; do not rely on it to maintain pH under load.

Conclusion: D‑valine solutions can be prepared across a range of pH values for experimental needs, but it is not recommended as a primary buffering agent.

Green Alternatives

For a fundamental chiral building block like D‑valine, the “alternative” question is usually about greener processes and reagents rather than replacing the amino acid itself.

• Greener coupling strategies (literature/general):
  • Prefer aqueous or water-lean peptide couplings using carbodiimide + Oxyma systems with in situ neutralization, reducing reliance on DMF/NMP.
  • Use less hazardous solvents: 2‑MeTHF or CPME for protection/deprotection sequences where solubility allows (typically with protected D‑valine derivatives).
  • Enzymatic methods (proteases, ligases, transaminases) can enable stereoselective transformations under mild, aqueous conditions.
• Protection/deprotection:
  • Select protecting groups removable under green conditions: Fmoc (base-labile, piperidine alternatives like piperazine/DBU in greener solvents), or enzymatic deprotection strategies where applicable.
• Waste minimization:
  • Employ solid-phase peptide synthesis with greener solvent swaps (e.g., EtOAc/MeOH rinses where compatible), on-resin metrics to reduce excess reagents, and microflow coupling to cut solvent.

Comparison (general):

• Traditional vs greener approach
  • Solvent: DMF/NMP/DCM → 2‑MeTHF/CPME/EtOAc (case-dependent)
  • Coupling: HATU/HBTU/HOAt → EDC·HCl + Oxyma/ethyl cyano(hydroxyimino)acetate, or DIC + Oxyma (reduced hazard)
  • Activation: Isolated NHS esters → in situ activation to minimize handling and waste

Note: Choice must balance EHS gains with solubility and performance of D‑valine derivatives.

Pharmaceutical Uses

No therapeutic claims are made. The following are formulation/manufacturing and synthesis contexts from general literature/practice:

• Chiral starting material:
  • D‑Valine serves as a chiral pool precursor for the synthesis of enantioenriched intermediates and auxiliaries in API process development, complementing L‑valine routes.
• Peptide manufacturing:
  • D‑valine residues are incorporated to modulate peptide conformation, reduce proteolysis, and adjust physicochemical properties; typically used via protected derivatives (e.g., Fmoc‑Val‑OH) in SPPS.
• Excipient perspective:
  • While amino acids (e.g., glycine, arginine) can function as stabilizers/tonicity agents, D‑valine is less common; any excipient usage would require pharmacopeial compliance and specification control. This item’s excipient status and pharmacopeial monographs are Not specified for this item; refer to CoA/Spec Sheet.
• Analytical standards:
  • Used as a chiral reference for release testing of D/L amino acid content in bioprocessing or impurity profiling.

Regulatory note: For research use only (per Product Data). Suitability for cGMP manufacturing or clinical applications is not implied and must be established independently.

Physical Properties

Only literature/computed values are provided below; they are NOT specifications for this item.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: 117.15 g/mol (literature)
• Acid–base properties (literature):
  • pKa1 (carboxyl): ~2.3–2.4
  • pKa2 (ammonium): ~9.6–9.7
  • Isoelectric point (pI): ~6.0
• LogP/logD (literature):
  • logP (neutral form, estimated): around −2 to −3; effective hydrophilicity is pH-dependent due to zwitterion formation.
• Solubility (literature, qualitative):
  • Freely soluble in water when adjusted away from pI; limited solubility near pI due to zwitterionic aggregation.
  • Sparingly soluble to insoluble in most nonpolar organic solvents (e.g., hexanes, toluene).
  • Better solubility in polar protic/aqueous media; can dissolve in water, dilute mineral acids, or dilute bases.
• Melting/decomposition (literature):
  • Many amino acids undergo decomposition/“melting” >300 °C; D‑valine reported to decompose on heating rather than exhibit a sharp melt.
• Density/refractive index: Not applicable for solids or not typically reported; Not specified for this item.
• Hygroscopicity: Generally low to moderate for branched, hydrophobic amino acids; handle under dry conditions to avoid caking (general guidance).

Always consult the item’s CoA for definitive, lot-specific properties.

Quality and Grades

• Item-specific grade: Moligand™ (as provided). Specific acceptance criteria (e.g., purity %, water content, optical purity) are Not specified for this item; refer to CoA/Spec Sheet.
• About Moligand™ (contextual, general):
  • The Moligand™ designation is typically used for compounds curated for small-molecule screening, chemogenomic, or ligand-discovery workflows. Such materials are generally suitable for assay development, SAR exploration, and library inclusion. Actual analytical targets (HPLC purity, enantiomeric excess, residual solvents, metal limits) are defined per lot on the CoA.
• Relevance for D‑Valine:
  • As a chiral pool reagent, D‑valine’s enantiomeric integrity is critical. Users should verify enantiomeric excess and absolute configuration on the supplied CoA, particularly for asymmetric synthesis or stereochemical benchmarking.
  • Water content and counter‑ion/trace salt levels can affect dissolution and coupling efficiency in peptide chemistry; check Karl Fischer/IC data if provided.
• Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.
• Analytical verification (recommended best practices):
  • Identity: 1H/13C NMR in D2O or DCl/D2O; optical rotation; chiral HPLC.
  • Purity: HPLC/UPLC with UV or ELSD; elemental analysis for salts/hydration; MS for mass confirmation.

For regulated uses or quantitative work, always consult and retain the specific CoA for your lot.

Reaction and Applications

D‑Valine is widely used as a chiral building block and reference standard. Key application families (general/literature):

• Peptide synthesis:
  • Incorporated as Val residues via protected forms (Fmoc‑Val‑OH, Boc‑Val‑OH) using HATU/HBTU/DIC+Oxyma protocols. The D‑residue introduces conformational constraints and protease resistance in peptides (general effect), useful for probe design and SAR.
• Chiral pool synthesis:
  • The α‑stereocenter enables preparation of enantioenriched auxiliaries, amides, esters, and ligands. D‑Valine-derived oxazolidinones, imidazolidinones, or tert‑butyl esters serve as chiral platforms.
• Resolution/derivatization:
  • Formation of diastereomeric salts or amides with racemic amines/acids can enable kinetic or classical resolution.
• Coupling to surfaces/labels:
  • Activation of the carboxyl group (e.g., NHS ester formation) permits conjugation to amines on polymers, nanoparticles, or supports for chiral environment studies.
• Biochemical assays:
  • Substrate/control for amino acid racemases, transaminases, and transport studies; D‑series usage helps distinguish stereospecific pathways (general information).
• Practical tips:
  • Avoid high temperatures/strong base during coupling to minimize racemization; employ Oxyma or HOAt-type additives and maintain 0–25 °C.
  • Convert to esters (e.g., benzyl, tert‑butyl) for protecting the carboxyl when performing N‑acylation; deprotect under mild conditions (H2/Pd for benzyl; TFA for tert‑butyl).

Reaction Conditions

General literature guidance for common operations with D‑valine and its derivatives (not item-specific specifications):

• Peptide coupling (solution or SPPS):
  • Solvent: DMF or NMP (typical); greener options like 2‑MeTHF/CPME case-by-case.
  • Reagents: HATU/HBTU (3–1.1 equiv) or DIC (1.1–1.5 equiv) + Oxyma (1.1–1.5 equiv).
  • Base: DIPEA (2–4 equiv) or NMM (2–4 equiv).
  • Temperature/time: 0–25 °C, 30 min–2 h for activated couplings; monitor by TLC/LC or Kaiser test (SPPS).
  • Expected yields: often 70–95% for well-optimized steps (literature ranges).
• Esterification (carboxyl protection):
  • Acid-catalyzed MeOH/EtOH (Fischer) is possible but may racemize; prefer DCC/DMAP with alcohol or use SOCl2/ROH at 0–25 °C, short times.
• Carbamate protection (Boc/Fmoc):
  • Boc2O, DIPEA, dioxane/H2O or MeCN, 0–25 °C, 1–3 h; or Fmoc‑Cl, Na2CO3 (aq)/dioxane biphasic, 0–25 °C, 1–2 h.
• Formation of activated esters:
  • NHS or pNP esters via DCC/DIC at 0–5 °C initial, then rt, minimizing base to suppress epimerization.
• Avoiding racemization:
  • Maintain pH ≤9 in aqueous couplings; in organic media, minimize exposure to strong bases and use coupling additives (Oxyma/HOAt). Keep reactions short and cool.

These conditions are representative starting points; optimize per substrate and scale. Always confirm stereochemical integrity post-reaction.

Safety and Handling

• GHS classification, signal word, H‑statements, and pictograms: Not specified for this item; refer to the product SDS for authoritative safety information.
• Expected hazard profile (general): Amino acids like D‑valine typically present low acute toxicity and are not strongly irritating. Nonetheless, laboratory prudence is required.
• Personal protective equipment (PPE):
  • Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile).
  • Use in a well-ventilated area; avoid creating dust/aerosols.
• Handling cautions:
  • Avoid inhalation of dust and contact with eyes/skin.
  • Prevent contamination with strong oxidizers; avoid strong acids/bases during storage.
• First aid (general guidance; follow SDS/ institutional protocol):
  • Inhalation: Move to fresh air. Seek medical advice 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; continue rinsing.
  • Ingestion: Rinse mouth. Seek medical advice if unwell.
• Fire safety:
  • Solid organic material; use water spray, CO2, dry chemical, or foam. Combustion may produce COx and nitrogen oxides.
• Spill/leak response:
  • Avoid dust; sweep up and collect in appropriate container for disposal according to local regulations.

Always defer to the SDS for definitive hazard classification and response procedures.

Solvent Selection

D‑Valine is a zwitterionic, hydrophobic amino acid; solvent choice is driven by pH and intended transformation rather than classical polarity scales.

• Solubility profile (literature/general):
  • Water: Good solubility when pH is adjusted away from the isoelectric point (pI ~6.0). Use dilute HCl (to protonate carboxylate) or dilute NaOH (to deprotonate ammonium) to enhance dissolution.
  • Alcohols: Limited solubility in MeOH/EtOH; may dissolve as salts or esters.
  • Polar aprotic (DMF, DMSO, NMP): Parent amino acid shows limited solubility; convert to esters (e.g., methyl/tert‑butyl) or protected forms (Boc‑/Fmoc‑Val‑OH) for better solubility in organic media.
  • Nonpolar solvents (hexanes, toluene, Et2O): Essentially insoluble.
• Practical recommendations:
  • For biochemistry/assays: Prepare aqueous stocks at 50–200 mM by adjusting pH to ~2–3 (HCl) or ~9–10 (NaOH). Filter-sterilize (0.22 μm) if sterility is required (general guidance).
  • For peptide coupling: Use protected derivatives (Boc‑Val‑OH, Fmoc‑Val‑OH) in DMF/NMP/DCM; couple with standard agents (HATU/HBTU/DIC+Oxyma).
• Comparison (general):
  • L‑Valine vs D‑Valine: Identical solvent behavior; selection is driven by stereochemical requirements.
  • Versus more polar amino acids (e.g., lysine): Lower inherent water solubility at pI due to hydrophobic isopropyl side chain; pH adjustment is more critical for dissolving D‑valine.

Storage and Reconstitution

• Storage (item-specific):
  • Store at −80 °C (per Product Data). Keep container tightly closed in a dry, inert atmosphere if possible. Minimize freeze–thaw and moisture exposure.
• Shipping (item-specific):
  • Shipped on dry ice packs + cold packs (per Product Data) to maintain low temperature.
• Stability notes (general):
  • Solid amino acids are typically stable when kept dry and cold. Avoid repeated warming cycles; aliquot if frequent access is required.
• Reconstitution (general guidance):
  • For aqueous stock: Add calculated volume of water, then adjust pH with dilute HCl or NaOH to move away from pI (~6.0) to enhance dissolution. Typical working concentrations: 50–200 mM.
  • For sterile applications: Filter through 0.22 μm after dissolution. Store aliquots at −20 to −80 °C to limit microbial growth and degradation; avoid multiple freeze–thaw cycles.
  • For organic-phase chemistry: Convert to protected derivatives (e.g., Boc‑/Fmoc‑Val‑OH, esters) to improve solubility in DMF/NMP/DCM.
• Specifications (item-specific values such as water content, optical rotation, purity, residual solvents): Not specified for this item; refer to CoA/Spec Sheet.

Always follow institutional SOPs and the product CoA/SDS for lot-specific stability and handling guidance.

Structure and Identity

Brief description: D‑Valine is the D-enantiomer of the branched-chain, aliphatic amino acid valine; a neutral, hydrophobic α‑amino acid used as a chiral building block and reference standard.

• Item-specific identifiers from Product Data:
  • SKU: D1499808
  • Product Name: D-Valine
  • CAS: 640-68-6
  • Grade: Moligand™
  • Category: 小分子和化合物库 (small molecules & compound library)
• Structural identifiers (literature):
  • Molecular formula: C5H11NO2 (literature)
  • Molecular weight: 117.15 g/mol (literature)
  • SMILES: CC(C)CC@HC(=O)O for L-valine; D-valine is the mirror image: CC(C)CC@@HC(=O)O (literature)
  • InChIKey (D-valine): KZSNJWFQEVHDMF-REOHCLBHSA-N (literature)
• Stereochemistry and functional groups:
  • One stereogenic center at the α‑carbon; configuration is D (R for valine under CIP in most depictions).
  • Functional groups: α‑amino (–NH2/–NH3+), α‑carboxylate (–CO2H/–CO2−), and an isopropyl side chain (hydrophobic, branched).
• 2D structure (described):
  • Backbone: –NH2–CH(R)–CO2H, where R = –CH(CH3)2.
  • At neutral pH, exists predominantly as the zwitterion NH3+–CH(R)–CO2−.
• Chirality note:
  • D‑Valine is the enantiomer of the proteinogenic L‑valine; D‑forms appear in bacterial cell wall components and some non‑ribosomal peptides (general information).

Synthetic Utility

D‑Valine is a versatile chiral building block. Key reactivity and transformations (general/literature):

• Functional group handles:
  • N‑terminus: amine (nucleophilic) for acylation, carbamate protection (Boc, Cbz, Fmoc).
  • C‑terminus: carboxylic acid for esterification (Me, tBu, Bn) and amide formation.
  • Side chain: isopropyl group is inert under most conditions, providing steric bias.
• Protecting group strategies:
  • N‑Boc or N‑Fmoc protects the amine; carboxyl protected as tBu/Bn/methyl esters. Orthogonality enables multi-step sequences.
• Named/typical reactions:
  • Peptide couplings with HATU/HBTU/TBTU, DIC/EDC + Oxyma/HOAt.
  • Formation of mixed anhydrides or acid chlorides followed by amide coupling (with care to suppress racemization).
  • Conversion to oxazolidinones/imidazolidinones for auxiliary-based asymmetric synthesis.
• Chiral induction/auxiliaries:
  • D‑Valine-derived auxiliaries impart predictable stereocontrol in aldol, alkylation, and Michael additions (case-dependent, literature precedent).
• Resolution chemistry:
  • Diastereomeric salt/amide formation with racemic partners for kinetic or classical resolution.

Practical notes:

• Maintain low temperatures and use racemization suppressors (e.g., Oxyma) during activation; avoid prolonged exposure to strong base.
• Verify enantiomeric purity after transformations (optical rotation, chiral HPLC) to ensure stereointegrity is preserved.

Target Specificity

Not applicable. This product is a small-molecule amino acid, not a biological targeting reagent (e.g., antibody/ligand with defined antigen specificity). No target, clone, or isotype information applies.