Chem. J. Chinese Universities ›› 2009, Vol. 30 ›› Issue (12): 2396.

• Articles • Previous Articles     Next Articles

Synthesis and Biological Activities of Xyloglucan Trisaccharides

LIU Hong-Mei1,3, BAI Xue-Fang1, DU Yu-Guang1*, DU Yu-Guo2,3   

  1. 1. The Natural Products and Glycoconjugate Research Group 1805, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China;
    2. State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China;
    3. Graduate University of Chinese Academy of Sciences, Beijing 100049, China
  • Received:2009-04-01 Online:2009-12-10 Published:2009-12-10
  • Contact: DU Yu-Guang. E-mail: duyg@dicp.ac.cn
  • Supported by:

    中国科学院知识创新工程项目(批准号: KSCX2-3-02-04)资助.

Abstract:

Native xyloglucan oligosaccharides are a kind of growth regulator in plant development. A xyloglucan trisaccharide: α-D-xylopyranosyl-(1,6)-β-D-glucopyranosyl-(1,4)-D-glucopyranose(1) and its derivatives were synthesized by three monosaccharide units. Glycosylation of isopropyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside(3) as the donor with 4-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-glucopyranoside(4) gave disaccharide(5). Deprotection of 4,6-O-benzylidene of compound 5 gave 6 as disaccharide acceptor. Then coupling of isopropyl 2,3,4-tri-O-benzyl-1-thio-β-D-xylopyranoside(2) with 6 afforded α and β trisaccharides(7) and separation of compound 7 gave 8(α) and 9(β). Global deprotection of compound 8 obtained trisaccharide 1. The whole route involves five steps and the total yield is 15%. Synthetic trisaccharides were added to the culture medium to detect their effects on tobacco growth. The results show that three synthesized oligosaccharides promote the growth of tobacco at the level of 1 mg/L. These results suggest that synthesized trisaccharides may be good prospects for the application in the control of plant growth.

Key words: Xyloglucan; Oligosaccharide; Tobacco; Growth regulator

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