SIOC English
有机化学
高级检索

有机化学 >

2013 , Vol. 33 >Issue 02: 245 - 258

DOI: https://doi.org/10.6023/cjoc201209013

综述与进展

阿拉伯、半乳和果呋喃寡糖的生物来源及合成进展

  • 梁兴勇 ,
  • 邓丽敏 ,
  • 杨劲松
展开
  • 四川大学华西药学院 成都 610041

收稿日期: 2012-09-10

  修回日期: 2012-11-02

  网络出版日期: 2012-11-14

基金资助

国家自然科学基金(Nos. 21172156, 21021001);科技部973课题(No. 2010CB833202)和教育部博士点基金(No. 20100181110082)资助项目.

收起

Review on Synthesis and Occurrence of Oligoarabino-, Oligogalacto- and Oligofructo-furanoses

  • Liang Xingyong ,
  • Deng Linmin ,
  • Yang Jinsong
Expand
  • West China School of Pharmacy, Sichuan University, Chengdu 610041

Received date: 2012-09-10

  Revised date: 2012-11-02

  Online published: 2012-11-14

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172156, 21021001), the National Basic Research Program of China (973 Program, No. 2010CB833202) and the Ph. D. Programs Foundation of Ministry of Education of China (No. 20100181110082).

Fold

摘要

由呋喃型阿拉伯糖、半乳糖和果糖构成的寡糖及其糖缀合物广泛分布于自然界, 主要存在于植物和低等生物, 如细菌、原生动物、真菌, 是细胞壁糖肽、糖脂和核苷酸糖类的重要组成部分, 具有广泛的生物学意义, 其合成和化学生物学研究一直备受关注. 综述了近年这些呋喃寡糖的生物来源及合成研究进展.

关键词： 阿拉伯呋喃糖; 半乳呋喃糖; 果呋喃糖; 寡糖; 合成; 生物来源

本文引用格式

梁兴勇 , 邓丽敏 , 杨劲松 . 阿拉伯、半乳和果呋喃寡糖的生物来源及合成进展[J]. 有机化学, 2013 , 33(02) : 245 -258 . DOI: 10.6023/cjoc201209013

Abstract

Oligofuranoses, such as oligoarabino-, oligogalato- and oligofructo-furanoses are widespread in plants and microorganisms. They are important structural constituents of cell wall glycoconjugates of bacteria, fungi and plants, and they have also been identified in glycopeptides, glycolipids as well as nucleotides. Synthesis of these oligofuranosyl structural fragments is holding current appeal. This review will focus on the occurrence and the chemical and chemo-enzymatic syntheses of these natural oligofuranoses.

Key words： arabinofuranose; galactofuranose; fructofuranose; oligosaccharide; synthesis; occurrence

参考文献

[1] Lowary, T. L. Curr. Opin. Chem. Biol. 2003, 7, 749.

[2] Miletti, L. C.; Marino, C.; Marino, K.; de Lederkremer, R. M.; Colli, W.; Alves, M. J. M. Carbohydr. Res. 1999, 320, 176.

[3] (a) Rose, N. L.; Completo, G. C.; Lin, S. J.; McNeil, M.; Palcic, M. M.; Lowary, T. L. J. Am. Chem. Soc. 2006, 128, 6721.
(b) Wing, C.; Errey, J. C.; Mukhopadhyay, B.; Blanchard, J. S.; Field, R. A. Org. Biomol. Chem. 2006, 4, 3945.

[4] (a) Chad, J. M.; Sarathy, K. P.; Gruber, T. D.; Addala, E.; Kiessling, L. L.; Sanders, D. A. R. Biochemistry 2007, 46, 6723.
(b) Kleczka, B.; Lamerz, A. C.; Zandbergen, G.; Wenzel, A.; Gerardy-Schahn, R.; Wiese, M.; Routier, F. H. J. Biol. Chem. 2007, 282, 10498.

[5] Peltier, P.; Euzen, R.; Daniellou, R.; Nugier-Chauvin, C.; Ferrières, V. Carbohydr. Res. 2008, 343, 1897.

[6] Collins, P.; Ferrier, R. Monosaccharides. Their Chemistry and Their Roles in Natural Products, John Wiley and Sons Ltd, Chichester, 1995, p. 57.

[7] (a) Brennan, P. J.; Nikaido, H. Annu. Rev. Biochem. 1995, 64, 29.
(b) Pedersen, L. L.; Turco, S. J. Cell. Mol. Life Sci. 2003, 60, 259.

[8] de Lederkremer, R. M.; Colli, W. Glycobiology 1995, 5, 547.

[9] Kamphuis, H. J.; Notermans, S.; Veeneman, G. H.; van Boom, J. H.; Rombouts, F. M. In Fungal Cell Wall and Immune Response, Eds.: Latgé, J. P.; Boucias, D.; NATO ASI Series, Springer-Verlag, Berlin, 1991, H53, p. 157.

[10] Tungland, B. C. ACS. Symp. Ser. 2003, 849, 135.

[11] Marino, C.; Gallo-Rodriguez, C.; de Lederkremer, R. M. In Glycans: Biochemistry, Characterization and Applications, Mora-Montes, H. M., Nova Science Publishers Inc, New York, 2012, p. 207.

[12] Gorshkova, R. P.; Kovalchuck, S. V.; Isakov, V. V.; Frolova, G. M. Bioorg. Khim. 1987, 13, 818.

[13] (a) Brennan, P. J. Tuberculosis 2003, 83, 91.
(b) Lowary, T. L. In Glycoscience: Chemistry and Chemical Biology, Eds.: Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Springer, Berlin, 2001, p. 2005.

[14] (a) Sorum, U.; Robertsen, B.; Kenne, L. Carbohydr. Res. 1998, 306, 305.
(b) Peltier, P.; Euzen, R.; Daniellou, R.; Nugier-Chauvin, C.; Ferrières, V. Carbohydr. Res. 2008, 343, 1897.

[15] Whitfield, C. Trends Microbiol. 1995, 3, 178.

[16] Linnerborg, M.; Weintraub, A.; Widmalm, G. Eur. J. Biochem. 1999, 266, 460.

[17] Clarke, A. J.; Bronner, D.; Keenleyside, W. J.; Severn, W. B.; Richards, J. C.; Whitfield, C. J. Bacteriol. 1995, 177, 5411.

[18] Beynon, L. M.; Richards, J. C.; Perry, M. B. Eur. J. Biochem. 1997, 250, 163.

[19] Sánchez-Medina, I.; Frank, M.; von der Lieth, C.-W.; Kamerling, J. P. Org. Biomol. Chem. 2009, 7, 280.

[20] van Zdorovenko, E. L.; Kachala, V. V.; Sidarenka, A. V.; Izhik, A. V.; Kisileva, E. P.; Shashkov, A. S.; Novik, G. I.; Knirel, Y. A. Carbohydr. Res. 2009, 344, 2417.

[21] Gerwig, G. J.; Kamerling, J. P.; Vliegenthart, J. F. G.; Morag-Morgenstern, E.; Lamed, R.; Bayer, E. A. Eur. J. Biochem. 1991, 196, 115.

[22] (a) Fischer, D.; Geyer, A.; Loos, E. FEBS J. 2006, 273, 137.
(b) Fischer, D.; Loos, E.; Geyer, A. Angew. Chem., Int. Ed. 2006, 45, 816.

[23] Kaneko, S.; Higashi, K.; Yasui, T.; Kusakabe, I. J. Ferment. Bioeng. 1998, 85, 518.

[24] (a) Barreto-Bergter, E.; Gorin, P. A. J.; Travassos, L. R. Carbohydr. Res. 1980, 86, 273.
(b) Latgé, J. P. M.; Kobayashi, H.; Debeaupuis, J. P.; Biaquin, M.; Sarfati, J.; Wieruszeski, J. M.; Parra, E.; Bouchara, J. P.; Fournet, B. Infect. Immun. 1992, 62, 5424.

[25] Parra, E.; Jiménez-Barbero, J.; Bernabé, M.; Leal, J. A.; Prieto, A.; Gomez-Miranda, B. Carbohydr. Res. 1994, 251, 315.

[26] Prieto, A.; Rupérez, A.; Hernàndez-Barranco, A.; Leal, J. A. Carbohydr. Res. 1988, 177, 265.

[27] Levery, S. B.; Toledo, M. S.; Straus, A. H.; Takahashi, H. K. Biochemistry 1998, 37, 8764.

[28] Ruda, K.; Lindberg, J.; Garegg, P. J.; Oscarson, S.; Konradsson, P. J. Am. Chem. Soc. 2000, 122, 11067.

[29] Agustí, R.; Giorgi, M. E.; Mendoza, V. M.; Gallo-Rodriguez, C.; de Lederkremer, R. M. Bioorg. Med. Chem. 2007, 15, 2611.

[30] Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1999, 121, 8499.

[31] Wu, Y.; Wang, D.-N. J. Nat. Prod. 2008, 71, 241.

[32] (a) Manisseri, C.; Gudipati, M. LWT-Food. Sci. Technol. 2010, 43, 421.
(b) Ferré, H.; Broberg, A.; Duus, J.; Thomsen, K. K. Eur. J. Biochem. 2000, 267, 6633.

[33] Westphal, Y.; Kühnel, S.; de Waard, P.; Hinz, S. W. A.; Schols, H. K.; Voragen, A. G. J.; Gruppen, H. Carbohydr. Res. 2010, 345, 1180.

[34] (a) Hincha, D. K.; Zuther, E.; Hellwege, E. M.; Heyer, A. G. Glycobiology 2002, 12, 103.
(b) Gambacorta, A.; Gliozzi, A.; De Rosa, M. World J. Microbiol. Biotechnol. 1995, 11, 115.

[35] (a) Yin, H.-Q.; Fu, H.-W.; Hua, H.-M; Pei, Y. H. J. Shenyang Pharm. Univ. 2006, 23, 641 (in Chinese). (尹宏权, 付红伟, 华会明, 裴月湖, 沈阳药科大学学报, 2006, 23, 641.)
(b) Kotiguda, G.; Peterbauer, T.; Mulimani, V. H. Carbohydr. Res. 2006, 341, 2156.
(c) Su, B.-N.; Pawlus, A. D.; Jung, H.-A.; Keller, W. J.; McLaughlin, J. L.; Kinghorn, A. D. J. Nat. Prod. 2005, 68, 592.

[36] (a) Lowary, T. L. J. Carbohydr. Chem. 2002, 21, 691.
(b) Peltier, P.; Euzen, R.; Daniellou, R.; Nugier-Chauvin, C.; Ferrières, V. Carbohydr. Res. 2008, 343, 1897.

[37] Zhang, G.-H.; Fu, M.-K.; Ning, J. Tetrahedron: Asymmetry 2005, 16, 733.

[38] Hölemann, A.; Stocker, B. L.; Seeberger, P. H. J. Org. Chem. 2006, 71, 8071.

[39] Completo, G. C.; Lowary, T. L. J. Org. Chem. 2008, 73, 4513.

[40] (a) D'Souza, F. W.; Lowary, T. L. Org. Lett. 2000, 2, 1493.
(b) Yin, H. F.; D’Souza, F. W.; Lowary, T. L. J. Org. Chem. 2002, 67, 892.
(c) Gurjar, M. K.; Nagaprasad, R.; Ramana, C. V. Tetrahedron Lett. 2002, 43, 7577.
(d) Sanchez, S.; Bamhaoud, T.; Prandi, J. Tetrahedron Lett. 2000, 41, 7447.
(e) Zhang, J.; Amin, A. G.; Höemann, A.; Seeberger, P. H.; Chatterjee, D. Bioorg. Med. Chem. 2010, 18, 7121.
(f) Han, J.; Gadikota, R. R.; McCarren, P. R.; Lowary, T. L. Carbohydr. Res. 2003, 338, 581.
(g) Marotte, K.; Sanchez, S.; Bamhaoud, T.; Prandi, J. Eur. J. Org. Chem. 2003, 3587.
(h) Lu, J.; Fraser-Reid, B. Org. Lett. 2004, 6, 3051.
(i) Lee, Y. J. Lee, K.; Jung, E. H.; Jeon, H. B.; Kim, K. S. Org. Lett. 2005, 7, 3263.

[41] Ishiwata, A.; Ito, Y. J. Am. Chem. Soc. 2011, 133, 2275.

[42] Fraser-Reid, B.; Lu, J.; Jayaprakash, K. N.; López, J. C. Tetrahedron: Asymmetry 2006, 17, 2449.

[43] Joe, M.; Bai, Y.; Nacario, R. C.; Lowary, T. L. J. Am. Chem. Soc. 2007, 129, 9885.

[44] Wang, H.-R.; Ning, J. J. Org. Chem. 2003, 68, 2521.

[45] Liang, X.-Y.; Deng, L.-M.; Liu, X.; Yang, J.-S. Tetrahedron 2010, 66, 87.

[46] Deng, L.-M.; Liu, X.; Liang, X.-Y.; Yang, J.-S. J. Org. Chem. 2012, 77, 3025.

[47] Gandolfi-Donadío, L.; Santos, M.; de Lederkremer, R. M.; Gallo-Rodriguez, C. Org. Biomol. Chem. 2011, 9, 2085.

[48] Rémond, C.; Plantier-Royon, R.; Aubry, N.; O'Donohue, M. J. Carbohydr. Res. 2005, 340, 637.

[49] Chlubnová, I.; Filipp, D.; Spiwok, V.; Dvo?áková, H.; Daniellou, R.; Nugier-Chauvin, C.; Králová, B.; Ferrières, V. Org. Biomol. Chem. 2010, 8, 2092.

[50] Kim, G.; Stork, G. J. Am. Chem. Soc. 1992, 114, 1087.

[51] Ito, Y.; Ogawa T. Angew. Chem., Int. Ed. 1994, 33, 1765.

[52] (a) Ishiwata, A.; Munemura, Y.; Ito, Y. Eur. J. Org. Chem. 2008, 64, 4250.
(b) Ishiwata, A.; Lee, Y. J.; Ito, Y. Org. Biomol. Chem. 2010, 8, 3596.

[53] (a) Gadikota, R. R.; Callam, C. S.; Wagner, T.; Fraino, B. D.; Lowary, T. L. J. Am. Chem. Soc. 2003, 125, 4155.
(b) Callam, C. S.; Gadikota, R. R.; Krein, D. M.; Lowary, T. L. J. Am. Chem. Soc. 2003, 125, 13112.
(c) Bai, Y.; Lowary, T. L. J. Org. Chem. 2006, 71, 9672.

[54] Zhu, X.-M.; Kawatkar, S. P.; Rao, Y.; Boons, G. J. J. Am. Chem. Soc. 2006, 128, 11948.

[55] Pedersen, C. M.; Crich, D. J. Org. Chem. 2007, 72, 1553.

[56] Ishiwata, A.; Akao, H.; Ito, Y. Org. Lett. 2006, 8, 5525.

[57] Imamura, A.; Lowary, T. L. Org. Lett. 2010, 12, 3686.

[58] (a) Lee, Y. J.; Lee, B. Y.; Jeon, H. B.; Kim, K. S. Org. Lett. 2006, 8, 3971.
(b) Lee, Y. J.; Lee, K.; Jung, E. H.; Jeon, H. B.; Kim, K. S. Org. Lett. 2005, 7, 3263.

[59] (a) Taper, H. S.; Lemort, C.; Roberfroid, M. B. Anticancer Res. 1998, 186A, 4122.
(b) Reddy, B. S. J. Nutr. 1999, 1297S, 1478S.
(c) Rozen, R.; Bachrach, G.; Bronshteyn, M.; Gedalia, I.; Steinberg, D. Microbiol. Lett. 2001, 195, 205.
(d) Vereyken, I. J.; Chupin, V.; Demel, R.; Smeekens, S. C. M.; De Kruijff, B. Biochim. Biophys. Acta 2001, 1510, 307.
(e) Huo, C.-X.; Wang, C.; Zhao, M.; Peng, S.-Q. Chem. Res. Toxicol. 2004, 17, 1112.

[60] Lian, G.-Y.; Gao, Q.; Lin, F. Carbohydr. Res. 2008, 343, 2992.

[61] (a) Krog-Jensen, C.; Oscarson, S. J. Org. Chem. 1996, 61, 4512.
(b) Krog-Jensen, C.; Oscarson, S. J. Org. Chem. 1998, 63, 1780.

[62] (a) Oscarson, S.; Sehgelmeble, F. W. J. Am. Chem. Soc. 2000, 122, 8869.
(b) Oscarson, S.; Sehgelmeble, F. W. J. Org. Chem. 2002, 67, 8457.
Options
文章导航

/

〈 〉