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研究生:葉濤欣
研究生(外文):David Wibowo
論文名稱:AntibacterialCelluloseFibersforHyaluronicAcidRecovery
論文名稱(外文):Antibacterial Cellulose Fibers for Hyaluronic Acid Recovery
指導教授:李振綱李振綱引用關係
指導教授(外文):Cheng-Kang Lee
學位類別:碩士
校院名稱:國立臺灣科技大學
系所名稱:化學工程系
學門:工程學門
學類:化學工程學類
論文種類:學術論文
論文出版年:2008
畢業學年度:96
語文別:英文
論文頁數:93
中文關鍵詞:Antibacterial activityBioseparationHyaluronic acidQuaternized cellulose fibers
外文關鍵詞:Antibacterial activityBioseparationHyaluronic acidQuaternized cellulose fibers
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This thesis was motivated by the practical need to develop a scalable and cost-effective separation method to recover hyaluronic acid (HA), a commercially valuable medical biopolymer, from bacterial culture broth. This challenge can potentially be addressed by taking advantage of the polyanionic character of HA. Through the electrostatic interaction with cationic matrix, HA is expected to be recovered. In this thesis quaternary ammonium modified cellulose fibers were used to recover HA directly from the Bacillus subtilis culture.
At the first stage of the studies, two variant of cellulose fibers were prepared by grafting different type of the antibacterial quaternary ammonium compound (QAC). Silane (3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride) and choline based ionic liquid analogue (sodium hydroxide and 2–chloroethyltrimethylammonium chloride based deep eutectic solvent) were used to quaternize the cellulose fibers surface. Results from elementary analysis, grafting ratio determination by weight measurement and Fourier transform infrared spectroscopy demonstrated that either silane or choline has been successfully grafted onto the surface of cellulose fibers after the chemical modification.
Prior to the adsorption studies, the antibacterial assessments were performed. It was shown that both silane modified cellulose fibers (SMC) and choline modified cellulose fibers (CMC) have antibacterial activity against E. coli and B. subtilis, with the former had better activity due to the presence of long alkyl chain on the quaternary ammonium groups of SMC. The antibacterial activity for E. coli is higher than that for B. subtilis due to the difference in cell wall structures. The feasibility of the antibacterial cellulose fibers on HA adsorption was then explored. Adsorption of HA onto the modified cellulose fibers was carried out at different pHs (3–8) and temperatures (277, 291, 310 K). Adsorption isotherms followed the Langmuir isotherm model and the adsorption was thermodynamically favorable. The maximum adsorption capacity for SMC and CMC was found to be 183.67 mg/g (at pH 4, 310 K) and 351.32 mg/g (at pH 7, 277 K), respectively. The adsorbed HA on SMC could be effectively desorbed as much as 90.11% by 1 N NaCl at pH 7 while changing the pH to 3 was effective to desorb 36.50% of HA from CMC. The adsorption capacity of SMC decreased to 49% after 3 cycles, whereas the capacity of CMC decreased to 89%.
Finally, the capability of the modified cellulose fibers on the recovery of HA directly from B. subtilis culture was demonstrated. SMC was used in this process rather than CMC due to its high desorption efficiency. The antibacterial effect of SMC caused by its strong hydrophobic character also good for HA recovery. One gram of SMC was able to adsorb 14.94 mg of HA directly from the B. subtilis culture. The adsorption capacity of SMC used in this recovery process was much less than in the equilibrium adsorption studies due to the competition adsorption occurred in the culture broth.
This thesis was motivated by the practical need to develop a scalable and cost-effective separation method to recover hyaluronic acid (HA), a commercially valuable medical biopolymer, from bacterial culture broth. This challenge can potentially be addressed by taking advantage of the polyanionic character of HA. Through the electrostatic interaction with cationic matrix, HA is expected to be recovered. In this thesis quaternary ammonium modified cellulose fibers were used to recover HA directly from the Bacillus subtilis culture.
At the first stage of the studies, two variant of cellulose fibers were prepared by grafting different type of the antibacterial quaternary ammonium compound (QAC). Silane (3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride) and choline based ionic liquid analogue (sodium hydroxide and 2–chloroethyltrimethylammonium chloride based deep eutectic solvent) were used to quaternize the cellulose fibers surface. Results from elementary analysis, grafting ratio determination by weight measurement and Fourier transform infrared spectroscopy demonstrated that either silane or choline has been successfully grafted onto the surface of cellulose fibers after the chemical modification.
Prior to the adsorption studies, the antibacterial assessments were performed. It was shown that both silane modified cellulose fibers (SMC) and choline modified cellulose fibers (CMC) have antibacterial activity against E. coli and B. subtilis, with the former had better activity due to the presence of long alkyl chain on the quaternary ammonium groups of SMC. The antibacterial activity for E. coli is higher than that for B. subtilis due to the difference in cell wall structures. The feasibility of the antibacterial cellulose fibers on HA adsorption was then explored. Adsorption of HA onto the modified cellulose fibers was carried out at different pHs (3–8) and temperatures (277, 291, 310 K). Adsorption isotherms followed the Langmuir isotherm model and the adsorption was thermodynamically favorable. The maximum adsorption capacity for SMC and CMC was found to be 183.67 mg/g (at pH 4, 310 K) and 351.32 mg/g (at pH 7, 277 K), respectively. The adsorbed HA on SMC could be effectively desorbed as much as 90.11% by 1 N NaCl at pH 7 while changing the pH to 3 was effective to desorb 36.50% of HA from CMC. The adsorption capacity of SMC decreased to 49% after 3 cycles, whereas the capacity of CMC decreased to 89%.
Finally, the capability of the modified cellulose fibers on the recovery of HA directly from B. subtilis culture was demonstrated. SMC was used in this process rather than CMC due to its high desorption efficiency. The antibacterial effect of SMC caused by its strong hydrophobic character also good for HA recovery. One gram of SMC was able to adsorb 14.94 mg of HA directly from the B. subtilis culture. The adsorption capacity of SMC used in this recovery process was much less than in the equilibrium adsorption studies due to the competition adsorption occurred in the culture broth.
ABSTRACT iv
ACKNOWLEDGEMENTS vi
TABLE OF CONTENTS viii
LIST OF FIGURES x
LIST OF TABLES xii
CHAPTER 1. INTRODUCTION 1
1.1. BACKGROUND 1
1.2. OBJECTIVES 3
1.3. THESIS ORGANIZATION 3

CHAPTER 2. LITERATURE REVIEW 5
2.1. NATURAL SOURCES OF HYALURONIC ACID AND ITS USES 5
2.2. STRUCTURE AND PHYSICAL PROPERTIES OF HYALURONIC ACID 8
2.3. HYALURONIC ACID PRODUCTION 10
2.3.1. Hyaluronic acid from vertebrate tissue 10
2.3.2. Hyaluronic acid from bacteria 12
2.3.3. Hyaluronic acid from genetically engineered bacteria 17
2.4. SURFACE MODIFICATION OF CELLULOSE FIBERS BY QUATERNARY AMMONIUM
COMPOUND FOR HYALURONIC ACID SEPARATION PURIFICATION 20
2.4.1. Silane modified cellulose fibers 24
2.4.2. Choline modified cellulose fibers 27
2.4.3. Antibacterial activity of quaternary ammonium modified
cellulose fibers 28

CHAPTER 3. MATERIALS AND METHODS 31
3.1. MATERIALS 31
3.2. PREPARATION OF QUATERNARY AMMONIUM MODIFIED CELLULOSE FIBERS AND ITS
CHARACTERIZATION 32
3.2.1. Preparation of silane- and choline-modified cellulose
fibers 32
3.2.2. Characterization 33
3.2.2.1. Elemental analysis 33
3.2.2.2. Determination of grafting ratio 34
3.2.2.3. Fourier transform infrared spectroscopy 34
3.3. ANTIBACTERIAL ASSESSMENT OF QUATERNARY AMMONIUM MODIFIED
CELLULOSE FIBERS 34
3.3.1. Antibacterial activity in static mode 34
3.4.2. Antibacterial activity in dynamic mode 35
3.4. ADSORPTION/DESORPTION EXPERIMENT 36
3.4.1. Time course measurement 36
3.4.2. Determination of optimum pH 37
3.4.3. Hyaluronic acid equilibrium adsorption isotherm 37
3.4.4. Desorption of hyaluronic acid from silane- and
choline-modified cellulose fibers 38
3.4.5. Repeated use of silane- and choline-modified cellulose
fibers 38
3.4.6. Determination hyaluronic acid concentration 39
3.5. HYALURONIC ACID RECOVERY FROM BACILLUS SUBTILIS CULTURE BY SILANE
MODIFIED CELLULOSE FIBERS ADSORPTION 40
3.5.1. Protein assay 40
3.5.2. Hyaluronic acid recovery from Bacillus subtilis culture 41

CHAPTER 4. RESULTS AND DISCUSSIONS 43
4.1. CHARACTERIZATION OF QUATERNARY AMMONIUM MODIFIED CELLULOSE FIBERS 43
4.2. ANTIBACTERIAL ASSESSMENT OF QUATERNARY AMMONIUM MODIFIED
CELLULOSE FIBERS 46
4.3. ADSORPTION/DESORPTION STUDIES OF HYALURONIC ACID 54
4.3.1. Time course measurement 54
4.3.2. Effect of pH 55
4.3.3. Effect of temperature and equilibrium adsorption isotherm
60
4.3.4. Thermodynamic analysis 63
4.3.5. Desorption of hyaluronic acid and repeated use of
silane- and choline-modified cellulose fibers 66
4.4. HYALURONIC ACID RECOVERY FROM BACILLUS SUBTILIS CULTURE BY SILANE
MODIFIED CELLULOSE ADSORPTION 70

CHAPTER 5. CONCLUSIONS 73
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