(2S)-6-amino-2-[bis(carboxymethyl)amino]hexanoic acid

• ChemBase ID: 152338
• Molecular Formular: C10H18N2O6
• Molecular Mass: 262.25972
• Monoisotopic Mass: 262.11648631
• SMILES: C(CCN)C[C@@H](C(=O)O)N(CC(=O)O)CC(=O)O
• Canonical SMILES: NCCCC[C@H](N(CC(=O)O)CC(=O)O)C(=O)O
• InChI: InChI=1S/C10H18N2O6/c11-4-2-1-3-7(10(17)18)12(5-8(13)14)6-9(15)16/h7H,1-6,11H2,(H,13,14)(H,15,16)(H,17,18)/t7-/m0/s1
• InChIKey: SYFQYGMJENQVQT-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-[bis(carboxymethyl)amino]hexanoic acid
• IUPAC Traditional name: (2S)-6-amino-2-[bis(carboxymethyl)amino]hexanoic acid
• Synonyms: (S)-N-(5-Amino-1-carboxypentyl)iminodiacetic acid; Nα,Nα-Bis(carboxymethyl)-L-lysine hydrate; N2,N2-Bis(carboxymethyl)-L-lysine; Lysine-N,N-diacetic Acid; AB-NTA; (5S)-N-(5-Amino-1-carboxypentyl)iminodiacetic Acid; (S)-N-(5-氨基-1-羧基戊基)亚氨基二乙酸; Nα,Nα-二(羧甲基)-L-赖氨酸 水合物

Database IDs

• CAS Number: 941689-36-7; 113231-05-3
• Beilstein Number: 9141770
• PubChem SID: 24848747; 162246483
• PubChem CID: 7019830

CALCULATED PROPERTIES

• Acid pKa: 3.1519098
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -6.0498934
• LogD (pH = 7.4): -9.058039
• Log P: -4.5778913
• Molar Refractivity: 60.048 cm^3
• Polarizability: 23.965641 Å^3
• Polar Surface Area: 141.16 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Off-White Solid
• Melting Point: >208°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (TLC)
• Empirical Formula (Hill Notation): C10H18N2O6 · xH2O

DETAILS

Sigma Aldrich - 14580

Analysis Note
may contain up ~2 mol water and ~10% inorganic salts
Other Notes
Tricarboxylic acid used for preparing chelating resins employed for the chromatography of proteins1
Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - A603250

A nitrilotriacetic acid derivative used as a metal chelating adsorbent for metal ion affinity chromatography. This method can be used for identification and rapid one-step purification of gene products expressed as fusion proteins with an oligo-histidine

REFERENCES

• Hochuli, E., et al.: J. Chromatography, 411, 177 (1987)
• Meredith, G.D., et al.: Bioconjugate Chem., 15, 969 (2004)