(S)-2,2'-((5-Amino-1-carboxypentyl)azanediyl)diacetic acid

Base Information

• Chemical Name: (S)-2,2'-((5-Amino-1-carboxypentyl)azanediyl)diacetic acid
• CAS No.: 113231-05-3
• Molecular Formula: C10H18N2O6
• Molecular Weight: 262.263
• Hs Code.: 2922509090
• European Community (EC) Number: 814-520-8
• DSSTox Substance ID: DTXSID401252965
• Nikkaji Number: J720.389F
• Wikidata: Q76393733
• Mol file: 113231-05-3.mol

Synonyms:113231-05-3;(S)-2,2'-((5-Amino-1-carboxypentyl)azanediyl)diacetic acid;N2,N2-Bis(carboxymethyl)-L-lysine;(5S)-N-(5-Amino-1-carboxypentyl)iminodiacetic Acid;(S)-N-(5-AMINO-1-CARBOXYPENTYL)IMINODIACETIC ACID HYDRATE;N,N-bis(carboxymethyl)-L-lysine;Lysine, N2,N2-bis(carboxymethyl)-;N2,N2-Bis(carboxymethyl)lysine;AB-NTA;nalpha,nalpha-bis(carboxymethyl)-l-lysine;(2S)-6-AMINO-2-[BIS(CARBOXYMETHYL)AMINO]HEXANOIC ACID;MFCD00237437;BCML;160369-83-5;N,N-biscarboxymethyl-L-lysine;SCHEMBL158632;SYFQYGMJENQVQT-ZETCQYMHSA-N;C10H18N2O6;DTXSID401252965;AMY10904;BCP24122;AKOS016845622;DS-4770;AC-25687;BP-21385;B4614;CS-0018032;Nalpha,Nalpha -bis (carboxymethyl)-L-lysine;A927288;J-002925;(S)-2,2'-((5-Amino-1-carboxypentyl)azanediyl)diaceticacid;(S)-2,2'-(5-amino-1-carboxypentylazanediyl)diacetic acid

Chemical Property of (S)-2,2'-((5-Amino-1-carboxypentyl)azanediyl)diacetic acid

Chemical Property:

• Vapor Pressure: 5.41E-13mmHg at 25°C
• Melting Point: 537.8 °C at 760 mmHg
• Refractive Index: 1.551
• Boiling Point: 537.8oC at 760 mmHg
• PKA: 1.67±0.10(Predicted)
• Flash Point: 279 °C
• PSA: 141.16000
• Density: 1.389 g/cm³
• LogP: -0.25990
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Aqueous Acid (Slightly), Methanol (Very Slightly, Heated), Water (Sparingly, Son
• XLogP3: -5.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 262.11648630
• Heavy Atom Count: 18
• Complexity: 291

Purity/Quality:

98%,99%, ^*data from raw suppliers

(5S)-N-(5-Amino-1-carboxypentyl)iminodiaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCN)CC(C(=O)O)N(CC(=O)O)CC(=O)O
• Isomeric SMILES: C(CCN)C[C@@H](C(=O)O)N(CC(=O)O)CC(=O)O
• Uses: (5S)-N-(5-AMINO-1-CARBOXYPENTYL)IMINODIACETIC ACID HYDRATE is 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 tag. The oligo-histidine tag serves as a high affinity binding sequence for the purification of fusion proteins via a metal chelating absorbent such as N-(5-Amino-1-carboxypentyl)iminodiacetic acid. Also soluble in DMSO:DMF 1:1 and DMSO:CH2Cl2 1:2

Technology Process of (S)-2,2'-((5-Amino-1-carboxypentyl)azanediyl)diacetic acid

There total 4 articles about (S)-2,2'-((5-Amino-1-carboxypentyl)azanediyl)diacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

Nα,Nα-bis(carboxymethyl)-Nε-(benzyloxycarbonyl)-L-lysine (113231-04-2) → N,N-bis(carboxymethyl)-L-lysine (113231-05-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 12h;

DOI:10.1002/chem.201101540

Reference yield:

Nα,Nα-bis[(tert-butyloxycarbonyl)methyl]-L-lysine tert-butyl ester (205379-08-4) → N,N-bis(carboxymethyl)-L-lysine (113231-05-3)

Guidance literature:

With ethandithiol; chlorotriisopropylsilane; phenol; trifluoroacetic acid; at 20 ℃; for 4h;

DOI:10.1021/ja050690c

Reference yield:

N6-[(benzyloxy)carbonyl]-L-lysine (1155-64-2,57705-97-2,67178-46-5,25931-47-9) → N,N-bis(carboxymethyl)-L-lysine (113231-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH / H₂O / 0 - 50 °C

2: H₂ / Pd-on-charcoal / methanol; H₂O / 2 h / 20 °C / 760.05 Torr

With sodium hydroxide; hydrogen; palladium on activated charcoal; In methanol; water;

DOI:10.1021/ac060509y

upstream raw materials:

N_α,N_α-bis(carboxymethyl)-N_ε-(benzyloxycarbonyl)-L-lysine

N^α,N^α-bis[(tert-butyloxycarbonyl)methyl]-L-lysine tert-butyl ester

N₆-[(benzyloxy)carbonyl]-L-lysine

N^α,N^α-bis[(tert-butyloxycarbonyl)methyl]-N^ε-benzyloxycarbonyl-L-lysine tert-butyl ester

Downstream raw materials:

2-[bis(carboxymethylamino)]-6-tert-butoxycarbonylaminohexanoic acid

mono(1-phenyl-2-methoxycarbonyl-2-propenyl)glutaric acid 5S-carboxy-5-[bis(hydroxycarbonylmethyl)amino]pentylamide

mono(1-(4-prop-2-ynyloxyphenyl)-2-methoxycarbonyl-2-propenyl) glutaric acid (5S)-carboxy-5-[bis(hydroxycarbonylmethyl)amino]pentylamide

N_α,N_α-bis(carboxymethyl)-N_ε-(benzyloxycarbonyl)-L-lysine

Refernces

• 1、 -. "Multifunctional polymer micelle for jointly conveying chemotherapeutic drugs and gene editing systems as well as preparation method and application thereof (by machine translation)". Paragraph 0065; 0067; 0069. . Retrieved 2020/04/29.
• 2、 Hirabayashi, Kazuhisa,Hanaoka, Kenjiro,Shimonishi, Manabu,Terai, Takuya,Komatsu, Toru,Ueno, Tasuku,Nagano, Tetsuo. "Selective two-step labeling of proteins with an off/on fluorescent probe". experimental part. p. 14763 - 14771. Retrieved 2012/02/06.