NMR Spectroscopic Analysis of Sulfated β-1, 3-Xylan and Sulfation Stereochemistry
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概要
- 論文の詳細を見る
A novel sulfated β-1, 3-xylan product was synthesized from algal cell wall microfibril homoxylan by the N, N-dimethylformamide (DMF)-SO_3 complex sulfation method. Antithrombin activity appeared in this product was 6.5 times higher than that of standard heparin. From the results of ^1H- and ^<13>C-NMR spectroscopic analyses by DQF-COSY and HMQC and an infrared spectroscopic analysis, it was revealed that the ordered structure of β-1, 3-xylan as a triple helix had decayed and the resulting conformational changes had been caused by the sulfation reaction. The sulfated positions on the C-4 hydroxyl groups of the xylose residues were determined from ^<13>C-NMR chemical shifts, and it was found that regioselective sulfation had occurred predominantly with the C-4 secondary hydroxyl groups to produce a mono-substituent. Another type of sulfation of β-1, 4-xylan that showed no regioselectivity is considered to have been due to the different conformation of both xylans chains such as the triple helix in β-1, 3-xylan and the double straight chain like cellulose in β-1, 4-xylan. Therefore, the different type of regioselective sulfation of β-1, 3- and β-1, 4-xylan was caused by the difference in steric hindrance due to these conformations. These different types of regioselective sulfation with different linkage positions are also discussed for the secondary hydroxyl groups in β-1, 3- and β-1, 4-glucan after chemoselective sulfation of the C-6 primary hydroxyl groups.
- 社団法人日本農芸化学会の論文
- 1997-08-23
著者
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NAKANISHI Hiroshi
National Chemical Laboratory for Industry
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YAMAGAKI Tohru
Department of Biochemistry, Saitama University
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TSUJI Yohji
Department of Biochemistry, Saitama University
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MAEDA Masaakira
Department of Biochemistry, Saitama University
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Tsuji Y
Osaka Prefecture Univ. Osaka Jpn
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Yamagaki T
Univ. Tokyo Tokyo Jpn
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Maeda Masaakira
Department Of Biochemistry Faculty Of Science Saitama University
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Nakanishi Hiroshi
National Institute Of Bioscience And Human-technology Aist
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Maeda M
Department Of Biofunctional Chemistry Graduate School Of Natural Science And Technology Okayama Univ
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