• Applied Chemistry for Engineering
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• v.30 no.3
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• pp.313-315
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• 2019

A new synthetic method for N-hydroxysuccinimide (NHS), which is widely used in fine chemical and cosmetic industries, was developed. In a conventional synthesis, NHS is obtained by reacting $NH_2OH$ with succinic anhydride in a yield of about 70% using strong acid as a catalyst, which has an advantage of obtaining NHS relatively easily. However, it is expensive because of using a high cost succinic anhydride. In order to overcome this issue, we developed a new synthetic method for NHS with a moderate yield of 80% using a low cost succinic acid instead of succinic anhydride, alongside a stable Lewis acid catalyst, Zn acetate. As a result of the economic evaluation, it was confirmed that the cost reduction effect was about 15%.

• Bulletin of the Korean Chemical Society
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• v.25 no.9
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• pp.1366-1370
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• 2004

Controlled pore glass bead was modified with bovine serum albumin (BSA), and glutathione (GSH) was immobilized through three kinds of linkers on top of BSA. Bis(3-sulfo-N-hydroxysuccinimide suberate) sodium salt $(BS^3)$, N-hydroxysuccinimide 3-(2-pyridyldithio)propionate (SPDP), or N-hydroxysuccinimide 4-maleimidobutyrate (GMBS) was introduced into the BSA-bound matrix. Subsequently, GSH was immobilized by addition of thiol side chain into the maleimido moiety, replacing a disulfide group, or formation of an amide group upon releasing 3-sulfo-N-hydroxysuccimide group. It was observed that conjugation methodology played a critical role for activity of the immobilized GSH. SDS-PAGE chromatogram showed that the matrix of glutathione immobilized on BSA through GMBS manifested high selectivity towards glutathione-S-transferase (GST) in cell lysate.

• Clean Technology
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• v.26 no.2
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• pp.91-95
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• 2020

A new eco-friendly synthetic method for N-hydroxysuccinimide (NHS), widely used in the pharmaceutical and fine chemical industries, is developed. Conventional synthesis method yields NHS of about 70% after its reaction with NH₂OH to succinic acid. In this method, NHS can be obtained using low-cost succinic acid, but a great deal of solvents are required as an extraction method to purify NHS, while the work-up process is complicated, resulting in low yield. In addition, there is a safety risk due to the high reaction temperature for commercial production, and it is not economical due to the high cost of production from the generation of much waste because of an acid catalyst and the use of various solvents. In order to make up for this shortcoming, this study used succinic anhydride as a raw material under low temperature reaction and developed a new eco-friendly industrial synthesis method using isobutyl alcohol for a single solvent and non-catalytic reaction. The economic evaluation confirms that there is a cost reduction effect of about 20%. In the future, based on this result, studies may establish a commercial production technology through scale-up research and proceed with foreign technology transfer.

• Membrane and Water Treatment
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• v.8 no.6
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• pp.613-623
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• 2017

We report the novel thin film composite RO membrane modified by graphene oxide. The thin film composite RO membrane was exposed to 2000 mg/l sodium hypochloride; thereafter it was subjected to different graphene oxide concentration ranging from 50 mg/l to 1000 mg/l in water. The resultant membrane was crosslinked with 5000 mg/l N-hydroxysuccinimide. The performance of different membranes were analysed by solute rejection and water-flux measurement. It was found that 100 mg/l graphene oxide exposure followed by 5000 mg/l N-hydroxysuccinimide treatment resulted in the membrane with the highest solute rejection of 97.78% and water-flux of 4.64 Liter per sqm per hour per bar g. The membranes were characterized by contact angle for hydrophilicity, scanning electron micrographs for surface morphology, energy dispersive X-Ray for chemical composition of the surface, Atomic force microscope for surface roughness, ATR-FTIR for chemical structure identification. It was found that the graphene oxide modified membrane increases the salt rejection performance after exposure to high-fouling water containing albumin. Highly hydrophilic, antifouling surface formation with the nanomaterial led to the improved membrane performance. Moreover, the protocol of incorporating nanomaterial by this post-treatment is simple and can be applied to any RO membrane after it is manufactured.

• Applied Chemistry for Engineering
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• v.5 no.5
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• pp.801-807
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• 1994

Lactose substituted styrene monomer, N-(p-vinylbenzyl)-D-lactonamide(VLA) was prepared by coupling the lactose lactone with p-vinylbenzylamine. The carboxyl group of biotin was activated with N-hydroxysuccinimide in the presence of N, N'-dicyclohexylcarbodiimide. Subsquently, biotin substituted styrene monomer, N-(p-vinylbenzyl)-biotinamide(VBA) was prepared by amidation of the activated biotin with p-vinylbenzylamine. Poly(vinylbenzylactonamide-co-vinylbenzylbiotinamide), p(VLA-co-VBA) were synthesized through radical polymerization from the synthetic monomers(VLA-VBA) by using various mole ratio. The percentages of yield were 67~71%. The copolymers were found amphlphilic which had hydrophilic lactose, hydrophobic vinylbenzyl and biotin site within the structure. IR and $^{13}C-NMR$ analysis on the monomers and copolymer were carried out.

• Journal of the Korean Chemical Society
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• v.36 no.2
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• pp.282-286
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• 1992

The reaction of N-hydroxysuccinimide with polyacrylic acid and polymethacrylic acid gave poly(N-acryloxysuccinimide)and poly(N-methacryloxysuccinimide), whose reaction with cephradine provided polyacryloylcephradine and polymethacryloylcephradine. The activities of these polymeric drugs were investigated in terms of minimum inhibitory concentration by the common twofold dilution technique. Polyacryloylcephradine revealed excellent antibacterial activity against Staphylococcus aureus ATCC 25923, Staphylococcus aureus FDA 209P, Bacillus subtilis ATCC 6633, Bacillus licheniformis ATCC 14580, Escherishia coli BE 1186 and Salmonella typhimurium TV 119. Polymethacryloylcephradine revealed excellent Staphylococcus aureus ATCC 25923, Staphylococcus aureus FDA 209P, Bacillus subtilis ATCC 6633, Escherichia coli Be 1186 and Salmonella typhimurium TV 119.

• Archives of Pharmacal Research
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• v.27 no.3
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• pp.273-277
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• 2004

In previous studies for the development of new anticonvulsants, we found that N-Cbz-$\alpha$-amino-N-alkylsuccinimides exhibited significant anticonvulsant activities in the Maximal electroshock seizure (MES) and Pentylenetetrazole induced seizure (PTZ) tests, and also their anticonvulsant activities were dependent on the N-alkyl substituents existent in their structures. Based on these estimations, N-Cbz-$\alpha$-amino-N-hydroxysuccinimide and various N-Cbz-$\alpha$-amino-N-alkoxysuccinimides were prepared in order to develop more active anticonvulsants and to examine the effects of N-hydoxy or N-alkoxy groups on their anticonvulsant activities. The (R)-or (S)-N-Cbz-$\alpha$-amino-N-hydroxysuccinimide and N-Cbz-$\alpha$-amino-N-alkoxysuccinimides were prepared from the corresponding (R)-or (S)-N-Cbz-aspartic acid through the known synthetic procedures. Their anticonvulsant activities in the MES and PTZ test were evaluated. All of these compounds except 3a showed significant anticonvulsant activities against the PTZ test, but these compounds were not active in the MES test. The most active compound in the PTZ test was (R)-N-Cbz-$\alpha$-amino-N-benzyloxysuccinimide (ED$_{50}$=62.5 mg/kg). In addition, the anti-convulsant activities of these compounds were dependent on their N-substited groups. The order of anticonvulsant activity against the PTZ test, as judged from the ED50 values for (R) series was N-benzyloxy > N-hydroxy > N-isopropoxy > N-methoxy > N-ethoxy; for the (S) series N-ethoxy > N-benzyloxy > N-methoxy > N-isopropoxy.y.

• Polymer(Korea)
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• v.37 no.4
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• pp.539-546
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• 2013

Amino group-terminated poly(N-isopropylacrylamide) (PNIPAAm-$NH_2$) was synthesized via a radical polymerization of N-isopropylacrylamide (NIPAAm) using 2-aminoethanethiol hydrochloride (AESH) as a chain transfer agent. The molecular weight of the PNIPAAm-$NH_2$ was controlled by changing the concentration of AESH. The LCST of the aqueous solution of PNIPAAm-$NH_2$ increased slightly with increasing the AESH concentration. Alginate-g-PNIPAAm copolymer was synthesized by grafting PNIPAAm-$NH_2$ onto sodium alginate using N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide and N-hydroxysuccinimide. The formation of the grafted copolymers was confirmed by FTIR spectroscopy, solubility in water, and SEM-EDS. Alginate-g-PNIPAAm also exhibited swelling-deswelling behavior. However, it showed a LCST at a slightly increased temperature compared to PNIPAAm. The swelling ratio of the alginate-g-PNIPAAm hydrogel increased with the increase of the grafted PNIPAAm content.

• Journal of the Korean Electrochemical Society
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• v.4 no.3
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• pp.109-112
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• 2001

An activated carbon paste electrode was modified with the N-Hydroxysuccinimide(NHS) layer and applied to determine the dopamine in the presence of an excess ascorbic acid using square-wave voltammetry. The electrochemical properties of the modified electrode were examined in the solution containing dopamine/ascorbic acid using cyclic voltammetry(CV): the separation between the oxidation peaks of dopamine and ascorbic acid was largely dependent on the pH of the sample solution and became maximum at pH 4.0. Hence, the square-wave voltammetric determination of dopamine was carried out in a pH 4.0, 100mM phosphate buffer saline(PBS) containing 140mM NaCl. The detection limit and response slop were improved from $1.0{\mu}M\;to\;5.0\times10^{-2}{\mu}M\;and\;from\;0.93{\mu}A/{\mu}M\;to\;6.1{\mu}A/{\mu}M$, respectively, upon modification of the electrode surface by NHS.

• Bulletin of the Korean Chemical Society
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• v.34 no.6
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• pp.1895-1898
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• 2013