Glu-lys - ≥95% , CAS No.5891-53-2

CAS: 5891-53-2 Cat. No.: G1041597 PubChem CID: 7015704

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: C(CCN)CC(C(=O)O)NC(=O)C(CCC(=O)O)N
• IUPAC Name: (2S)-6-amino-2-[[(2S)-2-amino-4-carboxybutanoyl]amino]hexanoic acid
• InChIKey: BBBXWRGITSUJPB-YUMQZZPRSA-N
• INCHI: 1S/C11H21N3O5/c12-6-2-1-3-8(11(18)19)14-10(17)7(13)4-5-9(15)16/h7-8H,1-6,12-13H2,(H,14,17)(H,15,16)(H,18,19)/t7-,8-/m0/s1
• Isomeri SMILES: C(CCN)C[C@@H](C(=O)O)NC(=O)[C@H](CCC(=O)O)N
• CAS alternativo: 5891-53-2
• PubChem CID: 7015704

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Dipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Dipeptides
• Alternative Parents: Glutamic acid and derivatives N-acyl-L-alpha-amino acids Alpha amino acid amides Medium-chain fatty acids Amino fatty acids Dicarboxylic acids and derivatives N-acyl amines Secondary carboxylic acid amides Amino acids Carboxylic acid salts Carboxylic acids Organic salts Organic zwitterions Organopnictogen compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Monoalkylamines
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha-dipeptide - Glutamic acid or derivatives - N-acyl-l-alpha-amino acid - N-acyl-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Alpha-amino acid or derivatives - Medium-chain fatty acid - Amino fatty acid - Dicarboxylic acid or derivatives - Fatty amide - N-acyl-amine - Fatty acyl - Fatty acid - Amino acid or derivatives - Carboxamide group - Carboxylic acid salt - Amino acid - Secondary carboxylic acid amide - Carboxylic acid - Organic salt - Hydrocarbon derivative - Primary aliphatic amine - Amine - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Organic zwitterion - Organonitrogen compound - Organooxygen compound - Primary amine - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
• External Descriptors: dipeptide

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: 275.300 g/mol
• XLogP3: -6.300
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 275.148 Da
• Monoisotopic Mass: 275.148 Da
• Topological Polar Surface Area: 156.000 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 321.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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

No item-specific, validated protocols are provided for this SKU. The following general, non-validated procedures are offered as guidance for research use only:

• Preparation of aqueous stock solution (general):

  • Weigh the desired amount quickly to minimize moisture uptake.
  • Dissolve in ultrapure water to 10–100 mM. If needed, adjust pH (6–8) for rapid dissolution.
  • Filter through 0.22 µm PVDF for sterile, particle-free solutions as required by your application.

• LC–MS system suitability standard (general):

  • Prepare 0.1–1.0 mM stock in water.
  • Dilute to 1–10 µM in 0.1% formic acid in water for positive-ion mode.
  • Inject 1–10 µL on a C18 column; verify retention and mass response daily.

• Enzyme assay substrate/control (general):

  • Prepare working solutions in assay buffer (e.g., 50 mM HEPES, pH 7.5; 100 mM NaCl) at the desired concentration range (e.g., 10–1000 µM).
  • Include appropriate blanks and standards for kinetic or endpoint analyses.

Adapt concentrations and volumes to your instrumentation and assay sensitivity. Consult the CoA/Spec Sheet for any item-specific constraints before use.

Biological Roles

Item-specific biological claims: None provided; for research use only.

Literature/general biology for Glu–Lys dipeptide:

• Metabolic context: Dipeptides arise during proteolysis and are substrates for dipeptidases and aminopeptidases. Glu–Lys reflects an acidic–basic residue junction encountered in many proteins.
• Transport: Small peptides are transported across membranes by proton-coupled oligopeptide transporters (e.g., PEPT1/PEPT2) in various tissues; Glu–Lys can be used to probe transporter specificity and kinetics in model systems.
• Enzyme interactions: Proteases with preference for basic residues (e.g., trypsin-like enzymes) and carboxypeptidases may differentially process Glu–Lys depending on sequence context and neighboring residues; isolated dipeptides serve as simplified probes for mechanistic studies.
• Analytical biomarkers: While the γ-glutamyl-ε-lysine isopeptide is a marker of transglutaminase-mediated crosslinking, the α-linked Glu–Lys dipeptide may be used as a reference or comparator in analytical workflows distinguishing isopeptide bonds (method development context).

Use limitations: No clinical or diagnostic claims are made for this product. Any biological roles described are general literature context to aid experimental design.

Buffer Applications

Not typically applicable. Glu-lys is a dipeptide, not a conventional buffering agent. While solutions of peptides can exhibit some buffering capacity near their pKa values, dedicated buffer systems (e.g., phosphate, acetate, HEPES, Tris) are preferred for controlled pH.

Practical note:

• If Glu–Lys is used in biochemical assays, dissolve it in an appropriate buffer chosen for the enzyme/system under study (e.g., 50 mM phosphate, pH 7.0; or 50 mM HEPES, pH 7.5), rather than relying on the peptide to maintain pH.
• Check compatibility of buffer ions with analytical detection (e.g., LC-MS prefers volatile buffers like ammonium formate/acetate).

Green Alternatives

Context: For aqueous-compatible peptide materials like Glu-lys, the greenest approach emphasizes water-based systems and minimizing hazardous organic solvents.

Greener practice options (general):

• Prefer water or aqueous buffers over organic media whenever feasible for dissolution and processing.
• If a co-solvent is required, consider bio-based, lower-toxicity solvents (e.g., glycerol, propylene glycol) in low percentages, or minimal DMSO with prompt dilution into water.
• Use room-temperature processes when possible to reduce energy consumption; avoid lyophilization cycles unless necessary.

Comparison (general considerations):

• Water vs DMSO: Water offers lowest hazard and waste impacts; DMSO increases solvency but adds disposal considerations.
• Aqueous acetate/phosphate buffers vs ACN-rich mobile phases: For LC separations, start with aqueous phases; only introduce acetonitrile or methanol to achieve needed retention/selectivity.

Waste and lifecycle:

• Employ microscale preparations, closed containers, and high-recovery vials to minimize waste.
• Segregate peptide-containing aqueous waste from halogenated organics to simplify compliant disposal.

Item-specific note: No formulation constraints are provided for SKU G1041597, so solvent choice should prioritize water first, guided by the assay’s requirements.

Pharmaceutical Uses

No item-specific pharmacopeial status or excipient role is provided for this product.

General formulation context (non-clinical, research only):

• Small dipeptides such as Glu–Lys can be used as model compounds in preformulation studies to evaluate peptide solubility, stability vs pH/ionic strength, and excipient compatibility in research settings.
• They may serve as surrogates in evaluating peptide adsorption to containers/filters and in optimizing lyophilization cycles (research method development).
• For LC/LC–MS quality controls, dipeptides are sometimes included as system suitability standards or retention-time markers.

Important: This product is designated For research use only. No medical, therapeutic, or clinical use is claimed or implied. It is not supplied with pharmacopoeial certification, and no dosage/formulation guidance is provided.

Physical Properties

Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for the free dipeptide Glu-Lys (approximate, for reference only):

• Molecular formula (literature): C11H21N3O5 (neutral form typical for Glu–Lys dipeptide)
• Molecular weight (literature): ~275.3 g/mol
• Appearance: Generally white to off-white solid (typical for small peptides)
• Solubility: Highly soluble in water; limited solubility in most organic solvents due to zwitterionic character (literature)
• pI/pKa: Multiple ionizable groups; overall behavior is amphoteric with protonation depending on pH (literature). Typical pKa values: Lys ε-NH3+ ~10.5, Glu γ-COOH ~4.1, terminal groups near 2–9 (literature ranges).
• Hygroscopicity: Small peptides can be hygroscopic and deliquescent under high humidity (general observation).

Important: The above values are general literature information for Glu–Lys and are not product specifications. For exact specifications (e.g., water content, residual solvents, counter-ions, salt form), consult the CoA/Spec Sheet for SKU G1041597.

Quality and Grades

Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

General notes for peptide/dipeptide quality:

• Common grades: Research grade (typical for screening libraries), analytical standard grade (tight purity and identity control), and peptide synthesis grade (low residual solvents and defined counter-ions). If HPLC purity is stated on the CoA, it reflects chromatographic assay of the main component peak area.
• Identity confirmation: Peptide materials are commonly verified by HPLC/UPLC retention time, exact mass (ESI-MS), and, where applicable, 1H NMR. For dipeptides, optical rotation or chiral HPLC may be used to confirm stereochemistry.
• Counter-ion/salt form: Peptides may be supplied as free base/acid or as salts (e.g., TFA, acetate). Counter-ion content can affect mass, solubility, and pH; check the CoA for this item.
• Residuals and elemental limits: For chromatographic/biological applications, limits on residual solvents, water content (Karl Fischer), and inorganic ions may be provided on the CoA. Absent explicit data, do not assume specific values.

Recommendation: Verify the exact grade, purity assay method, and salt form for SKU G1041597 on the CoA/Spec Sheet prior to quantitative or regulated uses.

Reaction and Applications

Item-specific application claims: Not provided in the Product Data.

Literature/general research applications for Glu–Lys dipeptide:

• Biochemical standard: Used as a reference standard for peptide mapping, LC-MS method development, and calibration in metabolomics or peptidomics workflows.
• Enzymology: Serves as a model substrate or product analog in studies of peptidases, aminopeptidases (e.g., cleavage at the N-terminus), and carboxypeptidases (C-terminal processing), as well as in assessing protease specificity for acidic–basic dipeptide junctions.
• Nutritional/physiology research: Dipeptides are transported by PEPT1/PEPT2 systems; Glu–Lys can be used to probe transporter activity and uptake kinetics (literature context).
• Transglutaminase studies: While the enzymatic crosslink is γ-glutamyl-ε-lysine (isopeptide), Glu–Lys can be a comparator in analytical methods distinguishing α-peptide vs isopeptide linkages.

Practical tips (general):

• Solution prep: Dissolve first in a small volume of water or buffer; adjust pH if needed to enhance dissolution. Filter sterilize (0.22 µm) for cell-free biochemical assays where sterility is desired.
• Avoid metal-catalyzed degradation: Work in plastic or passivated glassware for sensitive assays; include minimal handling time at elevated temperatures.
• Analytical detection: UV at 214 nm is typical for peptide bonds; derivatization (e.g., OPA for amines) can enhance detection sensitivity in HPLC methods if required.

Note: Adapt conditions to the target enzyme/system; verify concentration by amino acid analysis, UV (if derivatized), or quantitative NMR.

Reaction Conditions

Item-specific reaction conditions are not provided. Below are general, literature-based conditions relevant to dipeptide handling and simple derivatization:

• Coupling via carboxyl group (general):

  • Reagents: EDC·HCl (0.9–1.2 equiv) with NHS (1.0–1.2 equiv) in water or DMF/water, pH 5.0–6.0; then add amine nucleophile, adjust pH 7.5–8.5.
  • Temperature/time: 0–25 °C, 0.5–4 h activation; 1–16 h coupling.
  • Notes: Maintain pH windows to balance activation and suppress hydrolysis. Monitor by LC.

• Amine acylation on Lys ε-NH2 (general):

  • Reagents: NHS esters (1.1–2.0 equiv) in DMF or DMSO; buffer target solution at pH 8.0–8.5 (e.g., bicarbonate).
  • Temperature/time: 0–25 °C, 0.5–2 h.
  • Notes: Control stoichiometry to avoid over-acylation of the N-terminus if free.

• Deprotection/side reactions: If protected derivatives are used (not claimed for this product), conditions depend on protecting groups (e.g., Boc removal with TFA; Fmoc removal with piperidine). Not applicable unless using protected forms.

• Analytical monitoring: Use RP-HPLC (C18) with aqueous buffer (0.1% formic acid) and acetonitrile gradient; detect at 214 nm. LC–MS offers rapid verification of mass shifts after conjugation.

These are general guidelines; optimize to your specific reagents and purity targets.

Safety and Handling

Item-specific hazard information: Not specified for this item; refer to SDS. Signal word, H-statements, GHS classification, and pictograms are not provided in the Product Data.

General safe handling guidance for small, non-volatile peptides:

• Expected hazard profile: Typically considered of low acute toxicity and non-volatile, but handle as a laboratory chemical. Avoid inhalation of dust and contact with eyes/skin.
• PPE: Wear lab coat, nitrile gloves, and safety glasses. Use a dust mask or work in a fume hood if handling powders that may aerosolize.
• First aid (general): Rinse eyes/skin with water upon contact; seek medical attention if irritation persists. If inhaled, move to fresh air. If ingested, rinse mouth with water; do not induce vomiting; seek medical advice.
• Storage incompatibilities: Avoid strong oxidizers; store away from extreme heat and moisture to prevent degradation or aggregation.
• Spill/leak: Avoid creating dust; sweep up carefully and dispose of in accordance with institutional and local regulations.
• Decomposition: Peptides may degrade upon prolonged exposure to elevated temperature, moisture, or microbial contamination.

Always defer to the official SDS for SKU G1041597 for authoritative safety information and regulatory classifications.

Solvent Selection

Applicability: As a small, polar dipeptide, Glu-lys is primarily handled in aqueous media.

General guidance (literature-based):

• Polarity/miscibility: Highly polar and hydrophilic; typically freely soluble in water and aqueous buffers over a broad pH range due to multiple ionizable groups.
• Organic solvents: Poorly soluble in nonpolar solvents (e.g., hexanes, toluene). Limited solubility in alcohols; solubility may improve in polar aprotic solvents (e.g., DMSO) but water is preferred for most uses.
• pH effects: Solubility and charge state are strongly pH-dependent. Increased solubility is typical under acidic conditions (protonated amines) and remains high under basic conditions (deprotonated carboxylates).

Comparison snapshot (general):

• Water/buffer: Best choice for biochemical assays, stock solutions, and LC sample prep.
• DMSO: Acceptable for concentrated stocks when water is unsuitable; dilute promptly into aqueous media to avoid precipitation.
• Methanol/ethanol: Often insufficient alone; can be used as minor cosolvents with water.

Item-specific note: No solvent specification is provided for SKU G1041597. Prepare solutions using high-purity water (e.g., 18 MΩ·cm) or buffer appropriate for the downstream application, and verify compatibility empirically.

Storage and Reconstitution

Item-specific storage: Room temperature (as provided in Product Data). Shipped-in conditions: Not specified for this item; refer to CoA/Spec Sheet.

General best practices for peptides/dipeptides (literature guidance; not item specifications):

• Solid material: Store tightly sealed in a desiccator or with desiccant to limit moisture uptake. Protect from prolonged exposure to light and heat.
• Short-term solutions: Store aliquots at 2–8 °C and use within a few days to minimize degradation or microbial growth. Include a suitable preservative for extended refrigerated storage if compatible with the assay.
• Long-term solutions: Freeze at −20 °C or below in aliquots to avoid repeated freeze–thaw. Thaw on ice and mix gently.
• Reconstitution: Use high-purity water or appropriate buffer. Typical starting concentrations are 10–100 mM. Adjust pH if necessary to ensure complete dissolution. Filter sterilize (0.22 µm) for sensitive assays.
• Container considerations: Low-bind tubes/vials reduce adsorption losses for dilute solutions.

Always consult the SDS and CoA/Spec Sheet for SKU G1041597 for definitive storage, shipping, and stability guidance specific to the supplied lot.

Structure and Identity

Brief: Glu-lys is the dipeptide composed of glutamic acid (Glu) followed by lysine (Lys).

Item-specific (from Product Data):

• SKU: G1041597
• Product Name: Glu-lys
• CAS: 5891-53-2
• PubChem CID: 7015704
• InChIKey: 20203 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general structural information (for typical L-Glu-L-Lys):

• Typical peptide sequence: L-Glu–L-Lys (standard α-peptide bond between Glu C-terminus and Lys N-terminus)
• Functional groups: α-carboxylate (C-terminus), α-ammonium (N-terminus), Glu side-chain γ-carboxyl, Lys side-chain ε-amino
• 2D description: An α-amino-α-carboxyl backbone with the side chain of Glu as a three-carbon chain ending in a carboxylate, and the side chain of Lys as a four-carbon chain terminating in a primary amine; these are connected by a single peptide bond between Glu carbonyl carbon and Lys backbone nitrogen.

Notes:

• Stereochemistry, exact protonation state, and isomeric specification are not provided for this catalog item; consult the CoA/Spec Sheet for definitive structural identifiers.

Synthetic Utility

Item-specific synthetic grade or protecting-group pattern: Not specified for this item; refer to CoA/Spec Sheet.

General synthetic utility of Glu–Lys dipeptide:

• Building block/standard: Useful as a defined, minimal peptide motif combining an acidic residue (Glu) followed by a basic residue (Lys), enabling studies of sequence-dependent properties (charge distribution, ion-pairing) and serving as a standard in peptide analytics.
• Reference in SPPS development: Employed as a benchmark for coupling efficiency and side-chain protection strategies involving orthogonal protection of Glu (e.g., side-chain carboxyl) and Lys (ε-amine) during method development. Note: The catalog item is not claimed to be protected; protected derivatives are separate reagents.
• Derivatization platform: The free ε-amine (Lys) and γ-carboxyl (Glu) provide handles for conjugation chemistry (e.g., NHS ester acylation of Lys, carbodiimide-mediated coupling via Glu carboxyl) in model reactions.
• Analytical mapping: Serves to calibrate retention and ionization in LC–MS/MS methods aimed at larger acidic–basic peptides.

Caveat: When specific protecting groups, optical purity, or counter-ions are critical, procure the appropriately protected or enantiopure derivatives; do not assume such features for SKU G1041597 without CoA confirmation.

Target Specificity

Not applicable. This product is a small molecule/dipeptide, not an antibody or affinity reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.

For enzyme or transporter studies, any “specificity” discussed should be defined by the user’s chosen biological system and assay design.