Process in Preparation and application of hydrophilic chromatographic materials for separation of monosaccharides and oligosaccharides

Abstract

Abstract: Carbohydrates play a vital role in food science, medicine science, life science and other fields. Carbohydrates can be divided into monosaccharides, oligosaccharides and polysaccharides, among which monosaccharides and oligosaccharides are mostly soluble, which can not only serve as structural substances, but also have various biological activities such as antioxidation, anticancer, antibacterial and antiviral. Hydrophilic interaction chromatography makes up the deficiency of reverse phase liquid chromatography in the separation of carbohydrate compounds. This paper introduced the amino bonded stationary phase, amide bonded stationary phase, carbohydrate bonded stationary phase and zwitterionic bonded stationary phase suitable for the separation and analysis of monosaccharides and oligosaccharides by hydrophilic interaction chromatography, and the effects of chromatographic separation conditions such as acetonitrile content, buffer salt concentration, pH value of mobile phase and column temperature on the separation effect were also summarized, so as to provide certain reference for the separation and analysis of monosaccharides and oligosaccharides.

Key words: Monosaccharides, Oligosaccharides, Separation, Chromatographic stationary phase, Hydrophilic interaction chromatography（HILIC）

CLC Number:

Xiang Li Dan-Dan REN Long WU Hui ZHOU. Process in Preparation and application of hydrophilic chromatographic materials for separation of monosaccharides and oligosaccharides[J]. FOOD SCIENCE, 0, (): 0-0.

References

[1] HLADYSH S, OLESHCHUK D, DVO?áKOVá J, et al. Comparison of carboxybetaine with sulfobetaine polyaspartamides: Nonfouling properties, hydrophilicity, cytotoxicity and model nanogelation in an inverse miniemulsion[J]. Journal of Applied Polymer Science, 2022, 139(19): 52099. DOI: 10.1002/APP.52099.
[2] SELINA G. Saccharide Polymers Containing a Small Number of Monosaccharides[J]. Journal of Glycobiology, 2021, 10(4).
[3] Li Shaochen，LV Min，ZHANG Shaoyong, et al. Advances on Monosaccharides and Oligosaccharides: Structural Modifications and Bioactivities[J]. Mini Reviews in Medicinal Chemistry, 2021, 21(17): 2551-2566. DOI: 10.2174/1389557521666210125145321
[4] KIMURA M, OGURA M, AKAMATSU M, et al. Convenient preparation of an antigenic oligosaccharide from white kidney bean powder: A useful plant oligosaccharide for synthesis of immunoactive glycopolymer[J]. International journal of biological macromolecules, 2020, 153: 1016-1023. DOI: 10.1016/j.ijbiomac.2019.10.231.
[5] 蒋忠平, 张安强, 孙培龙. 植物来源寡糖的研究进展(综述)[J]. 浙江食用菌, 2009, 17(02): 36-39.
[6] SYKORA D, ?EZANKA P, ZáRUBA K, et al. Recent advances in mixed‐mode chromatographic stationary phases[J]. Journal of separation science, 2019, 42(1): 89-129. DOI: 10.1002/jssc.201801048.
[7] ZHANG Lu, DAI Qian, QIAO Xiaoqiang, et al. Mixed-mode chromatographic stationary phases: recent advancements and its applications for high-performance liquid chromatography[J]. TrAC Trends in Analytical Chemistry, 2016, 82: 143-163. DOI: 10.1016/j.trac.2016.05.011.
[8] WANG Jianzhong, WANG Jianshan, NING Xiaohui, et al. pH-dependent selective separation of acidic and basic proteins using quaternary ammoniation functionalized cysteine-zwitterionic stationary phase with RPLC/IEC mixed-mode chromatography[J]. Talanta, 2021, 225: 122084. DOI: 10.1016/j.talanta.2021.122084
[9] NOUWADE K, TFAILI S, CHAMINADE P. Investigation of stationary phases performance for eicosanoids profiling in RP-HPLC[J]. Analytical and Bioanalytical Chemistry, 2021, 413(26): 6551-6569. DOI: 10.1007/s00216-021-03618-8
[10] LIU Jing, LI Jing, YI Dan, et al. Non-derivatization strategy for the comprehensive characterization of neutral monosaccharide isomers and neutral disaccharide isomers using hydrophilic interaction liquid chromatography coupled to quadrupole/time-of-flight mass spectrometry[J]. Journal of Chromatography B, 2021, 1185: 122972. DOI: 10.1016/j.jchromb.2021.122972
[11] ALPERT A J. Hydrophilic-interaction chromatography for the separation of peptides, nucleic acids and other polar compounds[J]. Journal of chromatography A, 1990, 499: 177-196.DOI: 10.1016/s0021-9673(00)96972-3
[12] QIAO Lizhen, LI Hua, SHAN Yuanhong, et al. Study of surface-bonded dicationic ionic liquids as stationary phases for hydrophilic interaction chromatography[J]. Journal of chromatography A, 2014, 1330: 40-50.DOI: 10.1016/j.chroma.2014.01.020
[13] GENG Huiliang, JING Jie, ZHANG Feifang, et al. A polar stationary phase obtained by surface-initiated polymerization of hyperbranched polyglycerol onto silica[J]. Talanta, 2020, 209: 120525.DOI: 10.1016/j.talanta.2019.120525
[14] S Harshitha,R surya santhosh,SK. Baba Hussain,K S Natraj,A Srinivasa rao. Hydrophilic interaction liquid chromatography (HILIC)???A Powerful separation technique[J]. Journal of Drug Metabolism & Toxicology,2020,11(4). DOI: 10.1007/s00216-011-5308-5
[15] BUSZEWSKI B, NOGA S. Hydrophilic interaction liquid chromatography (HILIC)—a powerful separation technique[J]. Analytical and bioanalytical chemistry, 2012, 402: 231-247.DOI: 10.1007/s00216-011-5308-5
[16] 杨晨曦. 新型咪唑类亲水作用色谱固定相的制备及其色谱性能评价[D]. 青岛：青岛科技大学, 2018.https://kns.cnki.net/KCMS/detail/detail.aspx?dbname=CMFD201802&filename=1018831934.nh
[17] LINDEN J C, LAWHEAD C L. Liquid chromatography of saccharides[J]. Journal of chromatography A, 1975, 105(1): 125-133. DOI: 10.1016/j.ijbiomac.2019.10.231.
[18] 薛昆鹏, 胡帅, 屠炳芳, 等. 用于乳糖含量测定的新型氨基键合硅胶色谱固定相的制备及评价[J]. 色谱, 2018, 36(02): 94-99.DOI: 10.3724/SP.J.1123.2017.09022.
[19] 刘士佳, 乔晓强, 杨艳军, 等. 新型咪唑嵌合氨基亲水作用色谱固定相的制备及其色谱性能[J]. 色谱, 2014, 32(10): 1079-1083.DOI: 10.3724/SP.J.1123.2014.07022.
[20] SONG Liujun, ZHANG Haijuan, CHEN Jia, et al. Imidazolium ionic liquids-derived carbon dots-modified silica stationary phase for hydrophilic interaction chromatography[J]. Talanta, 2020, 209: 120518.DOI: 10.1016/j.talanta.2019.120518
[21] GUO Dandan, YANG Chenxi, QIU Ruchen, et al. A novel imidazolium bonding stationary phase derived from N-(3-aminopropyl)-imidazole for hydrophilic interaction liquid chromatography[J]. Journal of Chromatography A, 2020, 1625: 461331. DOI: 10.1016/j.chroma.2020.461331
[22] 黄晓佳, 王俊德, 刘学良, 等. 酰胺型键合相的简便制备及评价[J]. 色谱, 2002(03): 219-222.
[23] QU Jianbo, XU Yuliang, LIU Junyi, et al. Thermo-and pH-responsive polymer brushes-grafted gigaporous polystyrene microspheres as a high-speed protein chromatography matrix[J]. Journal of Chromatography A, 2016, 1441: 60-67.DOI: 10.1016/j.chroma.2016.02.072.
[24] FAN Fangbin, WANG Licheng, LI Yijing, et al. A novel process for the preparation of Cys-Si-NIPAM as a stationary phase of hydrophilic interaction liquid chromatography (HILIC)[J]. Talanta, 2020, 218: 121154.DOI: 10.1016/j.talanta.2020.121154.
[25] Li Zongying, Li Shuxiang, Zhang Feifang, et al. A hydrolytically stable amide polar stationary phase for hydrophilic interaction chromatography[J]. Talanta,2021,231. DOI: 10.1016/j.talanta.2021.122340.
[26] CAI Jianfeng, CHENG Lingping, ZHAO Jianchao, et al. A polyacrylamide-based silica stationary phase for the separation of carbohydrates using alcohols as the weak eluent in hydrophilic interaction liquid chromatography[J]. Journal of Chromatography a, 2017, 1524: 153-159.DOI: 10.1016/j.chroma.2017.10.005.
[27] 杨铎, 俞冬萍, 董雪芳, 等. 基于巯基-烯烃点击化学的聚丙烯酰胺型亲水作用色谱固定相的制备[J]. 分析化学, 2015, 43(10): 1439-1444. DOI: 10.11895/j.issn.0253-3820.141022.
[28] MORAVCOVá D, ?MELíK R, K?ENKOVá J. Separation of labeled isomeric oligosaccharides by hydrophilic interaction liquid chromatography – the role of organic solvent in manipulating separation selectivity of the amide stationary phase[J]. Journal of Chromatography A, 2021, 1651: 462303. DOI: 10.1016/j.chroma.2021.462303.
[29] TANG Tingfeng, GUO Dandan, HUANG Shaohua. Preparation and chromatographic evaluation of the hydrophilic interaction chromatography stationary phase based on nucleosides or nucleotides[J]. Analytical Methods, 2021, 13(3): 419-425.DOI: 10.1039/d0ay02016h.
[30] 谢桂芳, 苏本超, 谢晓霞, 等. 点击化学在食品安全检测中的应用研究进展[J]. 分析测试学报, 2021, 40(05): 648-655. DOI: 10. 3969 /j. issn. 1004 － 4957. 2021. 05. 004.
[31] CHU Changhu, LIU Renhua. Application of click chemistry on preparation of separation materials for liquid chromatography[J]. Chemical Society Reviews, 2011, 40(5): 2177-2188.DOI: 10.1039/c0cs00066c.
[32] SANTOYO-GONZALEZ F, HERNANDEZ-MATEO F. Silica-based clicked hybrid glyco materials[J]. Chemical Society Reviews, 2009, 38(12): 3449-3462.DOI: 10.1039/b909363j.
[33] FU Qing, GUO Zhimou, LIANG Tu, et al. Chemically bonded maltose via click chemistry as stationary phase for HILIC[J]. Analytical Methods, 2010, 2(3): 217-224. DOI: 10.1039/b9ay00151d.
[34] RATHNASEKARA R, EL RASSI Z. Polar silica-based stationary phases. Part II-Neutral silica stationary phases with surface bound maltose and sorbitol for hydrophilic interaction liquid chromatography[J]. Journal of Chromatography A, 2017, 1508: 24-32. DOI: 10.1016/j.chroma.2017.05.059.
[35] 许丹,刘建英,刘玉梅.β-环糊精及其衍生物增加客体分子水溶性的研究进展[J]. 食品工业科技, 2021, 42(16): 404-411. DOI: 10.13386/j.issn1002-0306.2020080221.
[36] POULSON B G, ALSULAMI Q A, SHARFALDDIN A, et al. Cyclodextrins: Structural, chemical, and physical properties, and applications[J]. Polysaccharides, 2021, 3(1): 1-31.DOI: 10.3390/polysaccharides3010001
[37] 李强, 李媛媛, 朱楠, 等. 基于氧化石墨烯的环糊精型色谱固定相的制备及在对映体分离与亲水色谱中的应用[J]. 分析化学, 2018, 46(09): 1455-1463. DOI: 10．11895 / j．issn．0253-3820．181337
[38] 用天, 吴凡, 肖红斌, 等. 木糖醇和麦芽糖醇型亲水作用色谱固定相的制备及其分离性能的评价[J]. 色谱, 2015, 33(09): 910-916. DOI：10.3724/SP.J.1123.2015.04024
[39] 汪锦才. 糖型有机聚合物整体柱的制备与应用研究[D]. 广州：广东药科大学, 2019:5-8. DOI: 10.27690/d.cnki.ggdyk.2019.000148.
[40] BROWN M U, SEONG H, MARGOSSIAN K O, et al. Zwitterionic Ammonium Sulfonate Polymers: Synthesis and Properties in Fluids[J]. Macromolecular Rapid Communications, 2022, 43(12): 2100678.DOI: 10.1002/marc.202100678.
[41] LIU Xuefang, JIANG Yu, ZHANG Feifang, et al. Preparation and evaluation of a polymer-based sulfobetaine zwitterionic stationary phase[J]. Journal of Chromatography A, 2021, 1649: 462229.
[42] Jiang W, Irgum K. Synthesis and evaluation of polymer-based zwitterionic stationary phases for separation of ionic species[J]. Analytical chemistry, 2001, 73(9): 1993-2003.DOI: 10.1021/ac000933d
[43] JANDERA P, JANáS P. Recent advances in stationary phases and understanding of retention in hydrophilic interaction chromatography. A review[J]. Analytica Chimica Acta, 2017, 967: 12-32.DOI: 10.1016/j.aca.2017.01.060
[44] 杨晨曦, 黄少华, 仇汝臣. 一种新型两性离子亲水作用色谱固定相的制备及其色谱性能评价[J]. 当代化工, 2018, 47(08): 1549-1552. DOI: 10.13840/j.cnki.cn21-1457/tq.2018.08.003.
[45] FARHADPOUR M, MAGHARI S, REZADOOST H, et al. A click tyrosine zwitterionic stationary phases for hydrophilic interaction liquid chromatography[J]. Journal of Chromatography a, 2020, 1621: 461045.DOI: 10.1016/j.chroma.2020.461045
[46] CAVICCHI K, DENG G, ANGEL J. RAFT copolymerization of ionic monomers towards diverse functional materials[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256.
[47] TRUONG N P, JONES G R, BRADFORD K G E, et al. A comparison of RAFT and ATRP methods for controlled radical polymerization[J]. Nature Reviews Chemistry, 2021, 5(12): 859-869. DOI: 10.1038/s41570-021-00328-8.
[48] LAMCH ?, WITEK K, JAREK E, et al. New mild amphoteric sulfohydroxybetaine-type surfactants containing different labile spacers: Synthesis, surface properties and performance[J]. Journal of colloid and interface science, 2020, 558: 220-229. DOI: 10.1016/j.jcis.2019.09.100.
[49] XU Dongyang, WEI Hongbo, ZHEN Yanxia, et al. Carboxylate phosphabetaine as a bifunctional organocatalyst for the intramolecular ring opening of oxetane[J]. Organic Chemistry Frontiers, 2019, 6(10): 1681-1685.DOI: 10.1039/c9qo00304e.
[50] 张飞, 左雄军, 付强, 等. 一种两性离子混合模式色谱固定相及其制备方法和应用:CN111389383B [P]. 2022-08-09.
[51] FARHADPOUR M, MAGHARI S, REZADOOST H, et al. A click tyrosine zwitterionic stationary phases for hydrophilic interaction liquid chromatography[J]. Journal of Chromatography a, 2020, 1621: 461045.DOI: 10.1016/j.chroma.2020.461045.
[52] LI Shuxiang, LI Zongying, ZHANG Feifang, et al. A polymer-based zwitterionic stationary phase for hydrophilic interaction chromatography[J]. Talanta, 2020, 216: 120927.DOI: 10.1016/j.talanta.2020.120927.
[53] QIAO Lizhen, YU Chunmei, SUN Ruiting. Preparation and comparison of three zwitterionic stationary phases for hydrophilic interaction liquid chromatography[J]. Journal of separation science, 2020, 43(6): 1071-1079.DOI: 10.1002/jssc.201901087.
[54] SONNENBERG R A, NAZ S, COUGNAUD L, et al. Comparison of underivatized silica and zwitterionic sulfobetaine hydrophilic interaction liquid chromatography stationary phases for global metabolomics of human plasma[J]. Journal of Chromatography A, 2019, 1608: 460419.DOI: 10.1016/j.chroma.2019.460419.
[55] SANTARELLI X, CABANNE C. Mixed mode chromatography: a novel way toward new selectivity[J]. Current Protein and Peptide Science, 2019, 20(1): 14-21.DOI: 10.2174/1389203718666171024121137.
[56] HALFPENNY A P, BROWN P R. Mixed mode chromatography via column switching for the simultaneous HPLC analysis of lonic and non-lonic nucleic acid constituents[J]. Chromatographia, 1986, 21: 317-320.DOI: 10.1007/bf02311602.
[57] 娄旭华, 左慧颖, 王媛, 等. 一种聚合型弱阳离子交换/亲水相互作用色谱固定相的制备及色谱性能[J]. 色谱, 2020, 38(04): 430-437.DOI: 10.3724/SP.J.1123.2019.08019.
[58] JANDERA P, URBAN J, ?KE?íKOVá V, et al. Polymethacrylate monolithic and hybrid particle-monolithic columns for reversed-phase and hydrophilic interaction capillary liquid chromatography[J]. Journal of Chromatography A, 2010, 1217(1): 22-33. DOI: 10.1016/j.chroma.2009.09.041.
[59] SI Tiantian, WANG Licheng, ZHANG Haixia, et al. A novel approach for the preparation of core-shell MOF/polymer composites as mixed-mode stationary phase[J]. Talanta, 2021, 232: 122459. DOI: 10.1016/j.talanta.2021.122459.
[60] LIU Delu, WANG Haiyan, LIANG Mengying, et al. Polymerized phosphonium ionic liquid functionalized silica microspheres as mixed-mode stationary phase for liquid chromatographic separation of phospholipids[J]. Journal of Chromatography A, 2021, 1660: 462676. DOI: 10.1016/j.chroma.2021.462676.
[61] FERREIRA C de C, GAMA M R, DA SILVA G S, et al. Synthesis and evaluation of a pentafluorobenzamide stationary phase for HPLC separations in the reversed phase and hydrophilic interaction modes[J]. Journal of separation science, 2018, 41(20): 3855-3862. DOI: 10.1002/jssc.201800522.
[62] FAN Chao, LIU Bei, LI Hui, et al. N-Vinyl pyrrolidone and undecylenic acid copolymerized on silica surface as mixed-mode stationary phases for reversed-phase and hydrophilic interaction chromatography[J]. Journal of Chromatography A, 2021, 1655: 462534. DOI: 10.1016/j.chroma.2021.462534.
[63] PENG Huanjun, WANG Xiang, PENG Jingdong, et al. Preparation and evaluation of surface-bonded phenylglycine zwitterionic stationary phase[J]. Analytical and bioanalytical chemistry, 2018, 410: 5941-5950. DOI: 10.1007/s00216-018-1211-7.
[64] SI Tiantian, WANG Shuai, ZHANG Haixia, et al. Design and evaluation of novel MOF–polymer core–shell composite as mixed-mode stationary phase for high performance liquid chromatography[J]. Microchimica Acta, 2021, 188: 1-9. DOI: 10.1007/s00604-021-04738-9
[65] REN Xiujun, HU Chengxia, GAO D, et al. Preparation of a poly (ethyleneimine) embedded phenyl stationary phase for mixed-mode liquid chromatography[J]. Analytica Chimica Acta, 2018, 1042: 165-173. DOI: 10.1016/j.aca.2018.09.049
[66] 肖震, 周卫强, 郭元亨, 等. 混合模式色谱固定相的研究和应用进展[J]. 现代化工, 2022, 42(S2): 407-415. DOI: 10．16606 /j．cnki．issn0253－4320．2022．S2．084.
[67] 马月云, 张丹丹, 李盈柔, 等. 基于混合模式色谱生物活性肽的分离研究进展[J]. 食品科学: 1-13. DOI：10.7506/spkx1002-6630-20220428-372.
[68] 熊偲凤. 以甜菜碱类材料为配基的色谱固定相制备与应用研究[D]. 西安：西北大学, 2018. https://kns.cnki.net/KCMS/detail/detail.aspx?dbname=CMFD201901&filename=1018106640.nh.
[69] LI Ruiping, ZHANG Yi, Charles C. Lee, et al. Development and validation of a hydrophilic interaction liquid chromatographic method for determination of aromatic amines in environmental water[J]. Journal of chromatography A, 2010, 1217(11): 1799-1805. DOI: 10.1016/j.chroma.2010.01.049.
[70] ZIOBROWSKI P, ZAPA?A L, ZAPA?A W. Studies on the retention behavior of quercetin, phenol, and caffeine as test substances on selected neutral and charged hydrophilic interaction liquid chromatography stationary phases[J]. Separation Science Plus, 2022, 5(7): 267-274. DOI: 10.1002/sscp.202200027.
[71] GUO Yong, BHALODIA N, FATTAL B, et al. Evaluating the adsorbed water layer on polar stationary phases for hydrophilic interaction chromatography (HILIC)[J]. Separations, 2019, 6(2): 19. DOI: 10.3390/separations6020019.
[72] 蒲江华, 赵峡, 韩文伟, 等. 亲水作用色谱在糖类化合物分析中的应用[J]. 分析测试学报, 2017, 36(01): 145-150. DOI: 10. 3969 /j. issn. 1004 － 4957. 2017. 01. 025.
[73] ALPERT A J. Effect of salts on retention in hydrophilic interaction chromatography[J]. Journal of Chromatography a, 2018, 1538: 45-53. DOI: 10.1016/j.chroma.2018.01.038.
[74] 周行, 陈佳, 张樱山, 等. 奎宁功能化聚乙烯咪唑修饰硅胶亲水相互作用色谱固定相的制备及应用[J]. 色谱, 2020, 38(04): 438-444. DOI: 10.3724/SP.J.1123.2019.06008.
[75] ZHAI Xingchen, ZHAO Haitian, ZHANG Min, et al. New stationary phase for hydrophilic interaction chromatography to separate chito-oligosaccharides with degree of polymerization 2-6[J]. Journal of Chromatography B, 2018, 1081: 33-40. DOI: 10.1016/j.jchromb.2018.02.024.
[76] ?ESLA P, VA?KOVá N, K?ENKOVá J, et al. Comparison of isocratic retention models for hydrophilic interaction liquid chromatographic separation of native and fluorescently labeled oligosaccharides[J]. Journal of chromatography A, 2016, 1438: 179-188. DOI: 10.1016/j.chroma.2016.02.032.
[77] 姜舸, 沈爱金, 郭志谋, 等. 糖类化合物在两性离子亲水作用色谱柱上的保留行为评价[J]. 色谱, 2015, 33(09): 929-933. DOI:10.3724/SP.J.1123.2015.05011.
[78] 成晓东, 李云萍, 贺银菊. 一种可控离子比例的两性亲水色谱固定相的制备及性能研究[J]. 色谱, 2019, 37(07): 683-691. DOI:10.3724/SP.J.1123.2019.01038.
[79] 余琼卫, 郑凤, 方凯敏, 等. 纳米氧化锆沉积硅胶色谱固定相的制备及亲水作用色谱行为[J]. 高等学校化学学报, 2019, 40(09): 1857-1865. DOI: 10．7503 /cjcu20190158.
[80] YAN Jun, SHI Songshan, WANG Hongwei, et al. Neutral monosaccharide composition analysis of plant-derived oligo-and polysaccharides by high performance liquid chromatography[J]. Carbohydrate polymers, 2016, 136: 1273-1280. DOI: 10.1016/j.carbpol.2015.10.028.
[81] FU Qing, LIANG Tu, LI Zhenyv, et al. Separation of carbohydrates using hydrophilic interaction liquid chromatography[J]. Carbohydrate research, 2013, 379: 13-17. DOI: 10.1016/j.chroma.2017.10.005.
[82] HAO Zhigang, XIAO Baiming, WENG Naidong. Impact of column temperature and mobile phase components on selectivity of hydrophilic interaction chromatography (HILIC)[J]. Journal of separation science, 2008, 31(9): 1449-1464. DOI: 10.1002/jssc.200700624.
[83] JANDERA P. Stationary and mobile phases in hydrophilic interaction chromatography: a review[J]. Analytica chimica acta, 2011, 692(1-2): 1-25. DOI: 10.1016/j.aca.2011.02.047.