Synthesis of plant arabinogalactans

doi:10.1007/s11458-009-0016-9

Front Chem Chin

2009, Vol. 4

Issue (1) : 10-31 https://doi.org/10.1007/s11458-009-0016-9

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Synthesis of plant arabinogalactans

Fanzuo KONG(

)

Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China

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Abstract

Plant arabinogalactans consisting of a b-(1?6)-linked D-galactopyranosyl oligosaccharide backbone with a-(1?2)-L-arabinofuranosyl branches are synthesized based on the 1,2-anhydro galactopyranose technique, orthogonal (methoxydimethyl)methyl (MIP) and (2-naphthyl)methyl (NAP) protection strategy, and selective acylation or glycosylation method. The third method is the most simple and effective and it is also used for the synthesis of arabinogalactans composed of a b-(1?6)-linked D-galactopyranosyl oligosaccharide backbone with a-(1?3)-L-arabinofuranosyl branches.

Keywords arabinogalactan oligosaccharide synthesis

Corresponding Author(s): KONG Fanzuo,Email:fzkong@rcees.ac.cn

Issue Date: 05 March 2009

Cite this article:

Fanzuo KONG. Synthesis of plant arabinogalactans[J]. Front Chem Chin, 2009, 4(1): 10-31.

URL:

https://academic.hep.com.cn/fcc/EN/10.1007/s11458-009-0016-9
https://academic.hep.com.cn/fcc/EN/Y2009/V4/I1/10

Fig.1 Synthesis of arabinogalactans based on 1,2-anhydrogalactose derivatives

Fig.2 Synthesis of simple arabinogalactans based on the MIP technique

Fig.3 Synthesis of the arabinogalactan hexasaccharide

Fig.4 Synthesis of arabinogalactans based on a combination of MIP and NAP protection

Fig.5

Fig.6 Synthesis of higher arabinogalactans

Fig.7 Synthesis of O-2 branched arabinogalactan tetrasaccharide by selective galactosylation

Fig.8 Synthesis of O-3 branched arabinogalactan tetrasaccharide from 1,2-O-isopropylidenated galactose

Fig.9

Fig.10 Synthesis of arabinogalactans by combination of selective glycosylation and deacetylation.

Fig.11

Fig.12 Synthesis of 2-branched arabinogalactans by selective deacetylation

Fig.13 Synthesis 3-branched arabinogalactans based on 3,6-selective protection of galactoside in combination with selective glycosylation

Fig.14

Fig.15 Synthesis of 3-branched arabinogalactans based on selective O-3 allylation in combination with selective O-6 deacetylation

Fig.16

Fig.17 Synthesis of arabinogalactans with alternative 2- and 3-arabinose branches

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