N-(5-Amino-1-carboxypentyl)iminodiacetic acid
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N-(5-Amino-1-carboxypentyl)iminodiacetic acid
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CAS No:
113231-05-3
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Formula:
C10H18N2O6
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Chemical Name:
N-(5-Amino-1-carboxypentyl)iminodiacetic acid
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Synonyms:
L-Lysine,N2,N2-bis(carboxymethyl)-;N2,N2-Bis(carboxymethyl)-L-lysine;Lysine-N,N-diacetic acid;N-(5-Amino-1-carboxypentyl)iminodiacetic acid;53: PN: WO2004025259 PAGE: 47 claimed protein;4: PN: WO2004072260 PAGE: 12 claimed protein;1: PN: US20050123932 PAGE: 1 claimed protein;AB-NTA;13: PN: US20080160089 PAGE: 30 claimed protein;(S)-2,2′-((5-Amino-1-carboxypentyl)azanediyl)diacetic acid;193416-02-3;1262616-35-2;1308825-43-5
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CAS No:
Characteristics
141.16000
-5.3
1.389g/cm3
>208°C
537.8ºC at 760 mmHg
279ºC
1.551
5.41E-13mmHg at 25°C
Safety Information
3
Moisture Sensitive
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
N-(5-Amino-1-carboxypentyl)iminodiacetic acid Use and Manufacturing
Na, Na-bis(carboxymethyl)-Ne-benzoxycarbonyl-L-lysine (Z-NTA) was synthesized from bromoacetic acid and Ne-benzoxycarbonyl-L-lysine. The protecting group Z (benzoxycarbonyl) was then removed by hydrogenation resulting in Na, Na-bis(carboxymethyl)-L-lysine (NTA) from which MANTA was synthesized as follows. NTA (0.262 g, 1 mmole) was dissolved in sodium hydroxide solution (aqueous, 3 mmole, 5 ml) together with tiny amount of inhibitor, and was cooled to 0 C. To this solution was added methacryloyl chloride (0.048 g, 1.2 mmole), and with slight delay, sodium hydroxide solution (aqueous, 1.2 mmole, 2 ml). Then the reaction was allowed to progress with stirring at room temperature for 2 hrs followed by extraction with equal volume of diethyl ether (anhydrous) to remove unreacted acid chloride. The water layer was acidified to pH23 with hydrochloric acid (aqueous, 6M) followed by repeated extraction with ethyl acetate (10 ml per time for 15 times) while being saturated by sodium chloride solid. Organic layers were combined, and dried over magnesium sulfate (anhydrous) overnight. After the drying agent was filtered off, the organic solvent was evaporated to obtain white solid, which was recrystallized from tetrahydrofuran. About 0.23 g of MANTA was obtained (yield 70%) with a melting point of 105107 C. TLC: MeOH/H20 (4/1), Rf=0.72. MW: 330.38 Da. C14H22N2O7. C %: 50.90 (50.86); H %: 6.71 (6.63); N %: 8.48 (8.41). 1H-NMR (DMSO-D6, 200 MHz): d=1.32-1.58 (m, 6H, CH2-(CH2)3); d=1.89 (s, 3H, CH3); d=3.04 (m, 2H, CO-NH-CH2); d=3.32 (t, 1H, CH2-CH(COOH)-N); d=3.46 (s, 4H, N-(CH2-COO)2); d=5.28, 5.60 (t, s, 2H, CH2); d=7.65 (t, 1H, CO-NH); d=12.40 (s, 2.7H, (COOH)3)Hydrate of Na, Na-bis (carboxymethyl) -L-Lysine acid (0.93 g, 3.54 mmol) Was added to 1.25 M hydrochloric acid (80 mL) dissolved in a methanol solution, Force mouth heat (70 C) reflux overnight, The reaction time is preferably 24 hours. Concentration under reduced pressure gave the product as compound (6) (1.33 g, 100%).Add 0.93 g (3.54 mmol) Nalpha, NalphaBis(carboxymethyl)-L-lysine hydrate into 1.25M hydrochloric acid dissolved in 80 mL methanol solution and heat to reflux at 70 C. overnight. The preferred reaction time is 24 hours. The product-compound 6 (1.33 g, 100%) is obtained after vacuum evaporation. (0043) Analysis of compound 6:IR (neat) 3430 (NH2), 2955 (NH) & 1738 (CO) cm-1. 1H NMR (CD3OD) 4.35 (d, 4 H, CH2CO), 4.27 (t, 1 H, CHCO), 3.85 (s, 3H, CHCOOCH3), 3.82 (s, 3H, CH2COOCH3), 2.97 (t, 2 H, CH2NH2), 2.01 (q, 2 H, CH2CH2CH2CH2), 1.75 (m, 2 H, CH2CH2CH2CH2), 1.61 (q, 2 H, CH2CH2CH2CH2). 13C NMR (CD3OD) 170.32 & 169.32 (CO), 67.48 (CH), 54.89 (CH2CO), 53.60 (CH3), 40.31 (CH2NH2), 28.50 (CH2CH2CH2CH2), 27.90 (CH2CH2CH2CH2), 23.97 (CH2CH2CH2CH2).
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
Computed Properties
Molecular Weight:262.26
XLogP3:-5.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:10
Exact Mass:262.11648630
Monoisotopic Mass:262.11648630
Topological Polar Surface Area:141
Heavy Atom Count:18
Complexity:291
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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N-(5-Amino-1-carboxypentyl)iminodiacetic acid
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