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Alkaline Degradation of Cellobiose, 3.6-Anhydro-4-O-(β-D-Gluc0pyranosyl)-D-Glucos...
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Alkaline Degradation of Cellobiose, 3.6-Anhydro-4-O-(β-D-Gluc0pyranosyl)-D-Glucose, 3,6-Anhydr0-4-0-Methyl-D-Glucose, and D-Glucose1
作者:
J.Martin Macleod,
LelandR. Schroeder,
期刊:
Journal of Wood Chemistry and Technology
(Taylor Available online 1982)
卷期:
Volume 2,
issue 2
页码: 187-205
ISSN:0277-3813
年代: 1982
DOI:10.1080/02773818208085129
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
The title compounds were degraded in 0.099M oxygen-free aqueous NaOH at 25°, and sometimes 45°. Cellobiose degraded primarily to 3-deoxy-2-C-hydroxymethyl-D-pentonic (“isosaccharinic”) acids, plus the series of 3- to 6-carbon 3-deoxyaldonic acids and glyceric acid also produced from glucose. No disaccharide acids Indicative of a “stopping” reaction were formed. However, formation of 3,4-dideoxy-5-hexulosonic acid from cellobiose indicates that elimination of OH-3, necessary for the “stopping” reaction, did occur, but that the glucosyloxy substituent at C-4 was also eliminated in the same reaction sequence. The major products from 3, 6-anhydro-4-0-methyl-D-glucose and 3,6-anhydro-4-0-(β-D-gluco-pyranosyl)-D-glucose (3,6-anhydrocellobiose), 3-deoxy-D-hexonic acids and 3-deoxy-2-C-hydroxymethylpentonic acids, respectively, also indicate primary reaction sequences involving multiple substituent elimination. However, in contrast to cellobiose, 3,6-anhydrocellobiose also yielded a disaccharide product indicative of a “stopping” reaction. Mechanisms are proposed to account for the primary products of each substrate.
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