欢迎登录材料期刊网

材料期刊网

高级检索

以葡萄糖为原料,经乙酰化、选择性脱C1位乙酰基、转化成三氯乙酰亚胺酯、与受体醇偶联和脱保护5步反应合成了11种不同碳链长度的烷基-β-D-吡喃葡萄糖苷.利用核磁共振、偏光显微镜和热失重分析法对其进行结构表征和性能测试.结果表明,当烷基-β-D-吡喃葡萄糖苷疏水烷基链长n为6~10时,均具有发泡和乳化性能,特别是正壬基-β-D-吡喃葡萄糖苷(n=9)具有更加优异的发泡和乳化性能;当烷基-β-D-吡喃葡萄糖苷疏水链的长度n≥7时,均具有热致液晶行为,特别是正十二烷基-βD-吡喃葡萄糖苷(n=12)和十四烷基-β-D-吡喃葡萄糖苷(n=14)能够形成更加稳定的液晶态.

参考文献

[1] Xu W,Osei-Prempeh C,Lema C,et al.Synthesis,Thermal Properties,and Cytotoxicity Evaluation of Hydrocarbon and Fluorocarbon Alkyl β-D-xylopyranoside Surfactants[J].Carbohydr Res,2012,349:12-23.
[2] Yakimchuk O D,Kotomin A A,Petel'skii M B,et al.Cleaning Action and Surfactant Properties of Alkyl Glucosides[J].Russ J Appl Chem,2004,77 (12):2001-2005.
[3] Persson C M,Claesson P M.Interfacial Behavior of n-Octyl β-D-glucopyranoside Compared to That of a Technical Mixture Consisting of Octyl Glucosides[J].Langrnuir,2000,16:10227-10235.
[4] Ogawa S,Asakura K,Osanai S.Freezing and Melting Behavior of an Octylβ-D-glucoside-water Binary System-inhibitory Effect of Octyl β-D-glucoside on Ice Crystal Formation[J].Phys Chem Chem Phys,2012,14:16312-16320.
[5] Akita H,Kawahara E,Kato K.Chemoenzymatic Synthesis of Rhodiooctanoside Isolated from Chinese Medicines,Rhodiolae Radix[J].Tetrahedron-Asymmetr,2004,15:1623-1629.
[6] Richard G,Morel S,Willemot R-M,et al.Glucosylation of α-Butyl-and α-Octyl-D-glucopyranosides by Dextransucrase and Alternansucrase from Leuconostoc Mesenteroides[J].Carbohydr Res,2003,338:855-864.
[7] Ferlin N,Duchet L,Kovensky J,et al.Microwave-assited Synthesis of Long-chain Alkyl Glucopyranosides[J].Carbohydr Res,2008,343:2819-2821.
[8] Bornaghi L F,Poulsen S-A.Microwave-accelerated Fischer Glycosylation[J].Tetrahadron Lett,2005,46:3485-3488.
[9] Adasch V,Hoffmann B,Milius W,et al.Preparation of Alkyl α-and β-D-Glucopyranosides Thermotropic Properties and X-Ray Analysis[J].Carbohydr Res,1998,314:177-187.
[10] Hashim R,Mirzadeh S M,Heidelberg T,et al.A Reevaluation of the Epimeric and Anomeric Relationship of Glucosides and Galactosides in Thermotropic Liquid Crystal Self-assemblies[J].Carbohydr Res,2011,346:2948-2956.
[11] TANG Qiue,SHI Shende,CHEN Langqiu,et al.Stereospecific Synthesis of Protected Gal(α1→2)Glc[J].Chinese Pharm J,2012,47(19):1592-1597(in Chinese).唐秋娥,史慎德,陈朗秋,等.保护的半乳糖基(α1→2)葡萄糖苷中间体的立体专一性合成[J].中国药学杂志,2012,47(19):1592-1597.
[12] Cheng H,Cao X,Xian M,et al.Synthesis and Enzyme-specific Activation of Carbohydrate-geldanamycin Conjugates with Potent Anticancer Activity[J].J Med Chem,2005,48:645-552.
[13] LI Lijuan.Study on the Determination of PAA Solubility and the Extraction Technology[J].Appl Chem Ind,2007,36(6):547-549(in Chinese).李丽娟.苯乙酸溶解度测定及提取工艺研究[J].应用化工,2007,36(6):547-549.
[14] ZHANG Yadong,WANG Zijian,GAO Xiaolei,et al.Structures and Properties of n-Dodecyl Glucoside[J].J East China Univ Sci-Tech(Nat Sci Ed),2002,28(2):208-211 (in Chinese).章亚东,王自健,高晓蕾,等.正十二烷基葡萄糖苷合成与结构性能表征[J].华东理工大学学报(自然科学版),2002,28(2):208-211.
[15] PEI Yuehu,HUA Huiming,LI Zhanlin,et al.Application of Nuclear Magnetic Resonance to the Determination of the Configuration of Glycoside Bond[J].Acta Pharm Sin,2011,46(2):127-131 (in Chinese).裴月湖,华会明,李占林,等.核磁共振法在苷键构型确定中的应用[J].药学学报,2011,46(2):127-131.
[16] Goodby J W,G(o)rtz V,Cowling S J,et al.Thermotropic Liquid Crystalline Glycolipids[J].Chem Soc Rev,2007,36(12):1845-2128.
上一张 下一张
上一张 下一张
计量
  • 下载量()
  • 访问量()
文章评分
  • 您的评分:
  • 1
    0%
  • 2
    0%
  • 3
    0%
  • 4
    0%
  • 5
    0%