Preparation and application of novel polysulfone chiral membranes for the separation of tryptophan enantiomers

JI Yibing; DUAN Feifei; HAO Dandan; CHEN Jianqiu

doi:10.11665/j.issn.1000-5048.20170108

Journal of China Pharmaceutical University > 2017 > 48(1): 53-59. > DOI: 10.11665/j.issn.1000-5048.20170108

JI Yibing, DUAN Feifei, HAO Dandan, CHEN Jianqiu. Preparation and application of novel polysulfone chiral membranes for the separation of tryptophan enantiomers[J]. Journal of China Pharmaceutical University, 2017, 48(1): 53-59. DOI: 10.11665/j.issn.1000-5048.20170108

Citation:

PDF (1876 KB)

Preparation and application of novel polysulfone chiral membranes for the separation of tryptophan enantiomers

More Information

Graphical Abstract

Abstract

Abstract

To preparate a novel polysulfone chiral membranes, β-cyclodextrin was functionalized with dodecanoyl chloride, and this modified β-cyclodextrin was then incorporated into polysulfone casting solution to form the dodecanoyl-β-cyclodextrin/polysulfone chiral membrane. Meanwhile, current studies have investigated the effect of adding different amount of dodecanoyl-β-cyclodextrin on the pure water flux, bovine serum albumin(BSA)rejection rate and enantioselectivity of the membranes. The morphology of the dodecanoyl-β-cyclodextrin/polysulfone chiral membrane was characterized by scanning electron microscopy(SEM). With the incorporation of dodecanoyl-β-cyclodextrin, the pore structure of the membrane changed significantly, with more finger-like pore structures appearing in the support layer. So the membrane water flux increased significantly, while the BSA rejection rate decreased. When the addition amount of dodecanoyl-β-cyclodextrin was in the range of 2% to 3. 5%, the enantiomeric excess increased with the addition of dodecanoyl-β-cyclodextrin. A complete separation of racemic tryptophan can be performed using this novel dodecanoyl-β-cyclodextrin/polysulfone chiral membrane-based separation system.
- dodecanoyl-β-cyclodextrin,
- polysulfone membrane,
- tryptophan enantiomers,
- chiral separation

FullText(HTML)

References (16)

References

[1]	Sueyoshi Y,Fukushima C,Yoshikawa M.Molecularly imprinted nanofiber membranes from cellulose acetate aimed for chiral separation[J].J Membrane Sci, 2010,357(1):90-97.
[2]	Bozkurt S, Yilmaz M, Sirit A. Chiral calix[4] arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid[J].Chirality,2012,24(2):129-136.
[3]	Higuchi A,Tamai M,Ko YA,et al. Polymeric membranes for chiral separation of pharmaceuticals and chemicals[J].Polymer Reviews,2010,50(2):113-143.
[4]	Zhang Z,Zhang M,Liu Y,et al. Preparation of L-phenylalanine imprinted polymer based on monodisperse hybrid silica microsphere and its application on chiral separation of phenylalanine racemates as HPLC stationary phase[J].Sep Purify Technol,2012,87:142-148.
[5]	Ma C,Xu XL,Ai P,et al. Chiral separation of D,L-mandelic acid through cellulose membranes[J].Chirality,2011,23(5):379-382.
[6]	Gumí T, Valiente M, Palet C. Elucidation of SR-propranolol transport rate and enantioselectivity through chiral activated membranes[J].J Membrane Sci, 2005,256(1/2):150-157.
[7]	Ingole PG, Bajaj HC, Singh K. Optical resolution of racemic lysine monohydrochloride by novel enantioselective thin film composite membrane[J].Desalination,2012,305:54-63.
[8]	Wang H D,Chu L Y,Song H,et al. Preparation and enantiomer separation characteristics of chitosan/β-cyclodextrin composite membranes[J].J Membrane Sci, 2007,297(1):262-270.
[9]	Shiomi K,Yoshikawa M.Multi-stage chiral separation with electrospun chitin nanofiber membranes[J].Sep Purif Technol, 2013,118:300-304.
[10]	Robl S,Gou L,Gere A,et al. Chiral separation by combining pertraction and preferential crystallization[J].Chem Eng Process:Process Intensific,2013,67:80-88.
[11]	Matsuoka Y,Kanda N,Lee Y M,et al. Chiral separation of phenylalanine in ultrafiltration through DNA-immobilized chitosan membranes[J].J Membrane Sci, 2006,280(1/2):116-123.
[12]	Meng J,Wei G,Huang X,et al. A fluorescence sensor based on chiral polymer for highly enantioselective recognition of phenylalaninol[J].Polymer,2011,52(2):363-367.
[13]	Xie R,Chu LY,Deng JG.Membranes and membrane processes for chiral resolution[J].Chem Soc Rev, 2008,37(6):1243-1263.
[14]	Higuchi A,Higuchi Y,Furuta K,et al. Chiral separation of phenylalanine by ultrafiltration through immobilized DNA membranes[J].J Membrane Sci,2003,221(1/2):207-218.
[15]	Singh K,Ingole PG,Bajaj HC,et al. Preparation,characterization and application of β-cyclodextrin-glutaraldehyde crosslinked membrane for the enantiomeric separation of amino acids[J].Desalination,2012,298:13-21.
[16]	Ionita M,Pandele AM,Crica L,et al. Improving the thermal and mechanical properties of polysulfone by incorporation of graphene oxide[J].Composites Part B:Engineering,2014,59:133-139.

[1]	WANG Songkai, ZOU Yuchen, SUN Shipeng, YAN Zhiye, TANG Weiwei, LI Ping, LI Bin. Recent advances in mass spectrometry imaging and its application in drug research[J]. Journal of China Pharmaceutical University, 2023, 54(6): 653-661. DOI: 10.11665/j.issn.1000-5048.2023091901
[2]	FENG Yang, XU Xiao, MO Ran. Advances in lymphatic targeted drug delivery system for treatment of tumor metastasis[J]. Journal of China Pharmaceutical University, 2020, 51(4): 425-432. DOI: 10.11665/j.issn.1000-5048.20200406
[3]	ZHOU Yeshu, WANG Yanmei, ZHANG Beiyuan, WU Shuaicong, YANG Lei, YIN Lifang. Research progress of inorganic nanomaterials in drug delivery system[J]. Journal of China Pharmaceutical University, 2020, 51(4): 394-405. DOI: 10.11665/j.issn.1000-5048.20200403
[4]	WEI Yuanyuan, YANG Fan, TANG Jie, YU Lifang. Advances in the research of anti-tuberculosis drugs[J]. Journal of China Pharmaceutical University, 2020, 51(2): 231-239. DOI: 10.11665/j.issn.1000-5048.20200215
[5]	HAN Xiu, QI Xiaole, WU Zhenghong. Advances in self-assemblied DNA nanocages as drug delivery systems[J]. Journal of China Pharmaceutical University, 2017, 48(6): 663-669. DOI: 10.11665/j.issn.1000-5048.20170605
[6]	CHEN Xing, KANG Yang, WU Jun. Advances in biodegradable functional polymers based protein drug delivery system[J]. Journal of China Pharmaceutical University, 2017, 48(2): 142-149. DOI: 10.11665/j.issn.1000-5048.20170203
[7]	JIANG Lu, CHEN Dandan, SUN Minjie, PING Qineng, ZHANG Can. Advances of wax matrix tablets[J]. Journal of China Pharmaceutical University, 2016, 47(4): 497-502. DOI: 10.11665/j.issn.1000-5048.20160418
[8]	YAO Guilin, WANG Haiyong, LU Tao. Advances of the uricosuric drugs[J]. Journal of China Pharmaceutical University, 2016, 47(4): 491-496. DOI: 10.11665/j.issn.1000-5048.20160417
[9]	LIU Yanhong, ZHOU Jianping, HUO Meirong. Advances in the tumor microenvironment-responsive smart drug delivery nanosystem[J]. Journal of China Pharmaceutical University, 2016, 47(2): 125-133. DOI: 10.11665/j.issn.1000-5048.20160201
[10]	WANG Ruoning, LIU Congyan, ZHOU Jianping, CHEN Jian, WANG Wei. Advances in the research of lipoprotein-based nano scale drug delivery systems[J]. Journal of China Pharmaceutical University, 2014, 45(1): 10-16. DOI: 10.11665/j.issn.1000-5048.20140102

Cited By

Get Citation

PDF

XML

Article views PDF downloads

Turn off MathJax

Article Contents

Abstract

References

Preparation and application of novel polysulfone chiral membranes for the separation of tryptophan enantiomers

Abstract

References

Related Articles

Catalog

Preparation and application of novel polysulfone chiral membranes for the separation of tryptophan enantiomers

Abstract

References

Related Articles

Catalog

Export File

Citation

Format

Content