Chinese Journal of Organic Chemistry >
Synthesis of the Trisaccharide Repeating Unit from Azospirillum brasilense Type Strain Sp7 and Its Effect on Plant Growth
Received date: 2017-06-27
Revised date: 2017-07-28
Online published: 2017-08-16
Supported by
Project supported by the National Science and Technology Pillar Program of China (No. 2015BAK45B01) and the National Natural Science Foundation of China (No. 21172257).
A natural trisaccharide α-D-rhamnopyanosyl-(1→3)-α-L-fucopyranosyl-(1→4)-β-D-xylopyranoside was synthesized from xylose glycoside donor, fucose glycoside donor and rhamnopyanosyl glycoside donor using α-D-xylopyranoside, β-L-fucopyranoside and α-D-rhamnopyranoside as the raw material respectively. This trisaccharide is a repeating-structure of the cell wall of the Azospirillum brasilense type strain Sp7. In the critical glycosylation reaction between rhamnopyanosyl glycoside donor and disaccharide receptor, full protected trisaccharide was regioselectivity builded. Streamlined the synthesis steps and the total yield of trisaccharide is 10% base on β-L-fucopyranoside. This route is suitable for mass preparation of target products. Preliminary determination of plant growth regulating activity of germination bed in sand culture showed that at 100 mg/L concen-tration, the trisaccharide raised the rate of emergence, the plant height and the leaf area by 11.0%, 13.1% and 87.8%, respectively. It was preliminarily concluded that this trisaccharide had certain plant growth regulating activity.
Xu Yiren , Zhang Jianjun , Dong Yanhong , Tan Weiming . Synthesis of the Trisaccharide Repeating Unit from Azospirillum brasilense Type Strain Sp7 and Its Effect on Plant Growth[J]. Chinese Journal of Organic Chemistry, 2017 , 37(11) : 2929 -2939 . DOI: 10.6023/cjoc201706036
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