L-薄荷基-β-D-乳糖苷的合成

食品科学 ›› 2013, Vol. 34 ›› Issue (4): 83-87.

L-薄荷基-β-D-乳糖苷的合成

卢高超,陈朗秋,唐秋娥,刘灯峰,李宏伟,陈丽

湘潭大学

收稿日期:2011-11-21 修回日期:2012-12-25 出版日期:2013-02-25 发布日期:2013-01-29
通讯作者: 陈朗秋 E-mail:chengood2003@263.net
基金资助:
湖南省自然科学基金资助项目;湘潭大学第七批大学生创新基金研究项目;博士科研启动费

Synthesis of L-Menthyl β-D-Lactoside

Received:2011-11-21 Revised:2012-12-25 Online:2013-02-25 Published:2013-01-29
Contact: Langqiu Chen E-mail:chengood2003@263.net

摘要/Abstract

摘要： 为了改进L-薄荷醇的热稳定性和水溶性，对其分子结构改造成糖苷化衍生物。以L-薄荷醇和α-乳糖为原料，经过乙酰化、偶联、脱保护三步反应合成了目标化合物L-薄荷基-β-D-乳糖苷（4），总收率达到42.3%。中间体和目标化合物的结构经过熔点、旋光、核磁共振、质谱等手段表征。热稳定性和溶解性测试结果表明，该化合物4热稳定性高，水溶性强。

Abstract: In order to improve the thermostability and water solubility for L-menthol, its molecular structure was modified as a glycosidation derivative. With L-menthol and α-lactose as raw materials, a target compound L-menthyl β-D-Lactoside (4) was synthesized by three-step of acetylation, coupling, and deprotection, the total yield was 42.3%. The intermediate product and target compound were analyzed by melting point, optical rotation, NMR and MS technology. The results have showed that the compound 4 has desirable thermostability and excellent water solubility.

中图分类号:

TS202.3

卢高超陈朗秋唐秋娥刘灯峰李宏伟陈丽. L-薄荷基-β-D-乳糖苷的合成[J]. 食品科学, 2013, 34(4): 83-87.

参考文献

[1] MEI Xiangdong, HENG Linsen, FU Mingkun, et al. Synthesis of ?-D-Glcp-(1→3)-[?-D-Glcp-(1→6)]-?-D-Glcp -(1→3)-?-D-Glcp-(1→6)-[?-D-Galp-(1→4)-?-D-Glcp-(1→3)]-?-D-Glcp-OLauryl, an oligosaccharide with anti-tumor activity[J]. Carbohydr. Res., 2005, 340: 2345-2351.
[2] 舒宏福. 新合成食用香料手册[M]. 北京: 化学工业出版社, 2005: 38-39.
[3] P?TRUI O, TAB?R? V. potential production of volatile oil content in foil and the menthol mint (menthe piperita L.) under the influence of fertilization in conditions in the lovrin[J]. Research Journal of Agricultural Science, 2011, 43 (1): 145-150
[4] RAPHAEL I. Naturally Occurring Glycosides [M]. UMich: Ohn Wiley, 1999.
[5] SAKATA I, IWAMURA H. Synthesis and properties of menthyl glycosides[J]. Agric Biol Chem, 1979, 43(2): 307-312.
[6] XIE Wan-cui, TANG Jian, Gu Xiao-hong, et al. Thermal decomposition study of menthyl-glycoside by TGC/SDTA, DSC and simultaneous Py-GC-MS analysis[J].J. Anal. Appl. Pyrolysis, 2007, 78(1): 180-184.
[7] MASTELI? J, JERKOVI? I, VINKOVI? M, et a1. Synthesis of Selected Naturally Occurring Glucosides of Volatile Compounds. Their Chromatographic and Spectroscopic Propeties[J]. Croatica Chemica Acta, 2004, 77(3): 491-500.
[8] CHEN Langqiu, KONG Fanzuo. Unusual ?-glycosylation with galactosyl donors with a C2 ester capable of neighboring group participation[J]. Tetrahedron Letters 2003, 44: 3691–3695.
[9] NOGUCHI K, NAKAGAWA H, YOSHIYAMA M, et al. Anomer-Selective Glucosylation of l-Menthol Using Lyophilized Cells of Saccharomyces cere visiae[J]. Jouranl of Fermentation and Bioengineering, 1998, 85(4): 436-438.
[10] 史慎德, 陈朗秋, 刘永青等. L-薄荷基-?-D-葡萄糖苷的合成[J]. 烟草科技, 2011, (4): 51-59.
[11] 杨锡洪, 解万翠, 王维民等. ?-D-吡喃葡萄糖苷类香料前体的合成及表征[J]. 食品科学, 2007, 28(11): 179-183.
[12] 谢万翠, 顾小红, 罗昌荣等. 薄荷醇糖苷的合成、纯化与表征[J]. 食品与生物技术学报, 2006, 25(5): 72-76.
[13] 史慎德, 陈朗秋, 刘永青等. L-薄荷基-?-D-半乳糖苷的合成新方法[J]. 广州化学, 2010, 35(3): 1-7.
[14] DO H, SATO T, KIRIMURA K, et al. Enzymatic synthesis of L-menthyl ?-maltoside and L-menthyl ?-maltooligosides from L-menthyl ?-glucoside by cyclodextrin glucanotransferase[J]. Journal of Bioscience and Bioengineering, 2002, 94(2): 119-123.
[15] CODéE J D C, CHRISTINA A E, WALVOORT M T C. Uronic acids in oligosaccharide and glycoconjugate synthesis[J]. Top Curr Chem, 2011, 301: 253-289.
[16] CEN Y, SAUVE A A. Efficient syntheses of clofarabine and gemcitabine from 2-deoxyribonolactone[J]. Nucleosides, nucleotides and nucleic acids, 2010, 29: 113-122.
[17] IBATULLIN F M, SHABALIN K A, J?NIS J V, et al. Reaction of 1,2-trans-glycosyl acetates with thiourea: a new entry to 1-thiosugars[J]. Tetrahedron Letters, 2003, 44: 7961-7964.
[18] CHEN Langqiu, SHI Shen-de， LIU Yong-qing, et al. Studies on the stereoselective synthesis of a protected ?-D-Gal-(1→2)-D-Glc fragment [J]. Carbohydr. Res., 2011, 346: 1250–1256.
[19] GOLA G,TILVE M J, GALLO-RODRIGUEZ C. Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-?-D-galactofuranosyl) trichloroacetimidate for 1,2-cis ?-D-galactofuranosylation[J]. Carbohydr. Res., 2011, 346: 1495–1502.
[20] IVANOVA I A, ROSS A J, FERGUSON M A J, et al. Parasite glycoconjugates. Part 9. Synthesis of dec-9-enyl ?-D-galactopyranosyl-(1→4)-?-D-mannopyranosyl Phosphate and its epimers at the D-galactose moiety, substrate analogues for the elongating ?-D-mannopyranosylphosphate transferase in the Leishmania[J]. J. Chem. Soc., Perkin Trans. 1, 1999, 1743-1753.
[21] DAVIS B G. Recent developments in oligosaccharide synthesis [J]. J. Chem. Soc. Perkin Trans. 1, 2000, 14: 2137-2160.
[22] 陈朗秋, 赖端, 宋志伟等. 寡糖的立体选择性合成策略[J]. 有机化学, 2006, 26(5): 627-642.
[23] 施里内著, 张书圣等译. 有机化合物的系统鉴定手册[M]. 北京: 化学工业出版社出版, 2007: 90-91.
[24] 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
[25] 蔡孟深, 李中军. 糖化学基础、反应、合成、分离及结构[M]. 北京: 化学工业出版社, 2006: 370-371.
[26] RIVERA-SAGREDO A, JIMéNEZ-BARBERO J, MARTíN-LOMAS M . N.m.r. studies of the conformation of analogues of methyl ?-D-lactoside in methyl sulfoxide-d6[J]. Carbohydr. Res., 1991, 221: 37-47.
[27] 刘振东. ?-D-五乙酰半乳糖制备方法的改进[J]. 北京服装学院学报(自然科学版), 2001, 2l (2): 17-20.