• Title/Summary/Keyword: Carboxyl groups

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Preparation and Surface Charge Characterization of Polystyrene Particles and Powders with Carboxyl and/or Poly(ethylene glycol) Groups

  • Kim, Bae-Joong;Kim, Seong-Hun;Park, Ki-Hong
    • Proceedings of the Korean Fiber Society Conference
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    • 2003.10a
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    • pp.94-94
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    • 2003
  • Cross-linked polystyrene (PS) particles with carboxyl and/or poly(ethylene glycol) units on surface were formed by an emulsifier-free emulsion polymerization using styrene, methacrylic acid (MA), and poly(ethylene glycol) dimethacrylate (PEG-diMMA) at pH 7, and followed by freeze-drying to give the corresponding powders. Monodisperse polymer particles could be obtained at a concentration of PEG-diMMA 1 mol% relative to styrene. Zeta potential of polymer surface was measured to be 91 mV at a polymer of PEG-diMMA 1 mol% and was dropped as the content of MA increased.

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Synthesis of Various Polymeric Prodrugs of Ibuprofen with PEG and Its Derivative as Polymeric Carriers

  • Lee, Chan-Woo
    • Macromolecular Research
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    • v.12 no.1
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    • pp.63-70
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    • 2004
  • We have synthesized various types of poly(ethylene glycol) (PEG)-ibuprofen conjugates by the nucleophilic substitution of bromo-terminated PEG with ibuprofen-Cs salt; PN (Pluronic) was also used in place of PEG. All the bromo-terminated PEGs and PN were obtained in high yield. Conversions of the terminal hydroxyl groups to bromo-termini were quantitative, as were the drug conjugation processes. The Ι$_1$$_3$values obtained from solutions of the ibuprofen-conjugated prodrugs are summarized in relation to those of ibuprofen in water and in aqueous solutions of the original PEG, PN, and several ordinary surfactants. We believe that the fully hydrophilic PEG is completely hydrated and forms no hydrophobic pocket by segment aggregation. These results indicate that the probe environment is significantly hydrophobic, particularly in the solution of prodrug PN, for which the ratio is similar to that obtained from typical micelles of surfactants. The results suggest, therefore, that the present synthetic method is very useful for preparing PEG-based prodrugs from pharmaceuticals having carboxyl functionalities.

Peptide Synthesis with Polymer Bound Active Ester. Ⅱ. Synthesis of Pyrazolone Resin and Its Application in Acylation Reaction

  • Jong-Bum Kim;Yoon-Sik Lee
    • Bulletin of the Korean Chemical Society
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    • v.12 no.4
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    • pp.376-379
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    • 1991
  • Pyrazolone group containing resin was tested as an acyl carrier in solid phase peptide synthesis. Several kinds of dipeptide derivatives were prepared by aminolysis reactions of Boc-amino acid-pyrazolone resin active ester with various carboxyl protected amino acid derivatives. It was found that the rates of aminolysis reactions were largely dependent on the bulkiness of the amino acid side chains, the carboxyl protecting groups, and the swelling property of the resin. All the dipeptide derivatives were obtained in high yield in 20-30 minutes, and the pyrazolone resin could be reused repeatedly in peptide synthesis without any change of its reactivity.

Crystal Structure and Thermal Properties of the Lanthanum(Ⅲ) Complex with Triethylenetetraaminehexaacetic Acid: $K_3$[La(TTHA)]· $5H_2O$

  • 김종혁;이석근
    • Bulletin of the Korean Chemical Society
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    • v.20 no.4
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    • pp.417-421
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    • 1999
  • The complex, K3[La(TTHA)]5H,O, was prepared and its crystal structure was analyzed by single crystal X-ray diffraction method. In the complex, the La(Ⅲ) ion adopts a ten-coordinate geometry with four nitrogen atoms and six carboxyl oxygen atoms from the same TTHA ligand molecule. Its coordination polyhedron can be described as a distorted bicapped square antiprism. Each [La(TTHA)]3- anion is linked by K+ cations via carboxyl groups of TTHA ligand to form a three dimensional crystal structure. The thermal properties were investigated by TG and DTA techniques in argon atmosphere. The materials resulting from thermal treatment were La(OH)3 and K2O which were identified by powder X-ray diffraction technique.

The Influence of Protecting Groups on the β-Sheet Structure Stability of Protected Peptides

  • 이진식;이동진
    • Bulletin of the Korean Chemical Society
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    • v.16 no.7
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    • pp.591-594
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    • 1995
  • The influence of protecting groups on the β-sheet-structure-stability of protected peptides was studied in organic solvents. α-amino groups, carboxyl groups and side chain functional groups of model peptides were protected by suitable groups commonly used in peptide synthesis. The difference of the solubilities of model peptides was investigated by the solvent-titration method by using IR absorption spectra. The β-sheet structure of model peptide in CH2Cl2 was easily disrupted by increasing the amounts of DMSO. The β-sheet-structure-stabilizing potentials of each protecting group showed similar behaviors except Npys, Mts and Z2. The result exhibits that the < SPβ > values of protected peptides are almost independent of the kinds of their protecting groups.

Anti-calcification of Bovine Pericardium for Bioprosthetic Heart Valves after Surface Modification with Hyaluronic Acid Derivatives

  • Hahn Sei Kwang;Ohri Rachit;Giachelli Cecilia M.
    • Biotechnology and Bioprocess Engineering:BBE
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    • v.10 no.3
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    • pp.218-224
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    • 2005
  • Surface modification of glutaraldehyde fixed bovine pericardium (GFBP) was success­fully carried out with hyaluronic acid (HA) derivatives. At first, HA was chemically modified with adipic dihydrazide (ADH) to introduce hydrazide functional group into the carboxyl group of HA backbone. Then, GFBP was surface modified by grafting HA-ADH to the free aldehyde groups on the tissue and the subsequent HA-ADH hydrogel coating. HA-ADH hydrogels could be prepared through selective crosslinking at low pH between hydrazide groups of HA-ADH and crosslinkers containing succinimmidyl moieties with minimized protein denaturation. When HA­ADH hydrogels were prepared at low pH of 4.8 in the presence of erythropoietin (EPO) as a model protein, EPO release was continued up to $85\%$ of total amount of loaded EPO for 4 days. To the contrary, only $30\%$ of EPO was released from HA-ADH hydrogels prepared at pH=7.4, which might be due to the denaturation of EPO during the crosslinking reaction. Because the carboxyl groups on the glucuronic acid residues are recognition sites for HA degradation by hyaluronidase, the HA-ADH hydrogels degraded more slowly than HA hydrogels prepared by the crosslinking reaction of divinyl sulfone with hydroxyl groups of HA. Following a two-week subcutaneous implantation in osteopontin-null mice, clinically significant levels of calcification were observed for the positive controls without any surface modification. However, the calcification of surface modified GFBP with HA-ADH and HA-ADH hydrogels was drastically reduced by more than $85\%$ of the positive controls. The anti-calcification effect of HA surface modification was also confirmed by microscopic analysis of explanted tissue after staining with Alizarin Red S for calcium, which followed the trend as observed with calcium quantification.

Biosorption Model for Binary Adsorption Sites

  • Jeon, Choong;Park, Jae-Yeon;Yoo, Young-Je
    • Journal of Microbiology and Biotechnology
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    • v.11 no.5
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    • pp.781-787
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    • 2001
  • The binding of heavy metals by a biosorbent with binary functional groups was mathematically modeled. An FT-IR spectrophotometer analysis was employed to determine the stoichiometry between the protons in the functional groups of alginic acid and lead ions as a model system. The results calculated using an equilibrium constant agreed well with the experimental results obtained under various operating conditions, such as pH and metal ion concentration. It was also shown that the overall adsorption phenomenon of alginic acid was mainly due to its carboxyl groups. The equilibrium constants for each functional group successfully predicted the lead adsorption of ${\alpha}$-cellulose. Furthermore, the biosorption model could predict the adsorption phenomena of two metal ions, lead ions and calcium ions, relatively.

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Characterization of Functional Groups of Protonated Sargassum polycystum Biomass Capable of Binding Protons and Metal Ions

  • Yun, Yeoung-Sang
    • Journal of Microbiology and Biotechnology
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    • v.14 no.1
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    • pp.29-34
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    • 2004
  • Biosorption technology is recognized as an economically feasible alternative for the removal and/or recovery of metal ions from industrial wastewater sources. However, the structure of biosorbents is quite complex when compared with synthetic ion-exchange resins, which makes it difficult to quantify the ion-binding sites. Accordingly, this report describes a well-defined method to characterize the pK values and numbers of biomass functional groups from potentiometric titration data. When the proposed method was applied to Sargassum polycystum biomass as a model biosorbent, it was found that the biomass contained three types of functional groups. In addition, the carboxyl group (pK=$3.7{\pm}0.09$) was found to be the major binding sites ($2.57{\pm}0.06 mmol/g$) for positively-charged heavy-metal ions.

Biosorption of Reactive Dyes using Chemically Modified Sewage Sludge (화학적으로 변형된 하수슬러지를 이용한 반응성염료의 생물흡착)

  • Han, Min-Hee;Choi, Gi-Wook;Yun, Yeoung-Sang
    • Clean Technology
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    • v.13 no.3
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    • pp.215-221
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    • 2007
  • Biosorption is considered to be a promising alternative to replace the present methods for the treatment of dye-containing wastewater. In this study, sewage sludge was used as a biosorbent which could be one of the cheapest and most abundant biomaterials. The objective of this work is to develop a surface-modified biosorbent with enhanced sorption capacity and binding affinity. The FT-IR and potentiometric titration studies revealed that carboxyl, phosphateand amine groups played a role in binding of dye molecules. The binding sites for reactive dye Reactive Red 4 (RR 4) were identified to be amino groups present in the biomass. In this work, based on the biosorption mechanism, the performance of biosorbentcould be enhanced by the removal of inhibitory carboxyl groups from the biomass for practical application of the biosorbents. As a result, the maximum capacity of biomass was increased up to 130% and 210% of the increment of sorption capacity at pH 2 and 4, respectively. Therefore, chemically modified sewage sludge can be used as an effective and low-cost biosorbent for the removal of dyes from industrial discharges.

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Repairing Damaged Hair Using Pentapeptides of Various Amino Acid Sequences with Crosslinking Reaction

  • Choi, Wonkyung;Son, Seongkil;Song, Sang-Hun;Kang, Nae Gyu;Park, Sun-gyoo
    • Korea Journal of Cosmetic Science
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    • v.2 no.1
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    • pp.11-19
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    • 2020
  • The aim of this study is to investigate the effect of various pentapeptides on hair repair depending on the characteristics of comprising amino acids using crosslinking agents in hair. Total ten peptides were synthesized with two kinds of amino acids respectively, of which were previously categorized according to R group of the amino acids contributing to the characteristic of each peptide: STTSS (Ser-Thr-Thr-Ser-Ser), LIILL (Leu-Ile-Ile-Leu-Leu), CMMCC (Cys-Met-Met-Cys-Cys), DEEDD (Asp-Glu-Glu-Asp-Asp), RKKRR (Arg-Lys-Lys-Arg-Arg), TAMRA-STTSS, TAMRA-LIILL, TAMRA-CMMCC, TAMRA-DEEDD, and TAMRA-RKKRR. Pentapeptide alone, or pentapeptides with crosslinking agents such as polymeric carbodiimide (PCI) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) were treated to chemically damaged hair. Hair diameter and break strength (N = 40/case) were measured to calculate tensile strength of hair for computing hair repair ratio, and fluorescence yields (N = 20/case) were collected for hair treated with TAMRA-peptides. The tensile strength of hair treated with pentapeptides alone, or pentapeptides with cross-linking agents is consistent with the fluorescence yield from the microscope images of the cross-sectioned hair in vision and in numerical values. Pentapeptides consisting of hydrophobic amino acids (LIILL), amino acids with sulfur (CMMCC), and basic amino acids (RKKRR) increased the tensile strength in perm-damaged hair. Pentapeptides with no extra carboxyl/amine groups in R group of amino acids resulted in no significant differences in hair strength and fluorescence yield among hairs treated with alone and with crosslinkers. Pentapeptides with extra carboxyl groups or amine groups enabled further strengthening of hair due to increased bonds within the hair after carbodiimide coupling reaction. The hair repairs of pentapeptides with various amino acid sequences were studied using crosslinking. Depending on the physical characteristics of comprising amino acids, the restoration of damaged hair was observed with tensile strength of hair and fluorescence signals upon cross-sectioned hair in parallel to possibly understand the binding tendency of each pentapeptide within the hair.