Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Phosphorylated Glycans Produced from Nonreducing Mono- and Oligosaccharides by the Action of P2O5 in Dimethyl Sulfoxide, and Their Interactions with Concanavalin A
Shigehiro HIRANOTomikazu NISHIOTatsuro ITO
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1975 年 39 巻 10 号 p. 1963-1967

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The action of P2O5 in DMSO on methyl α-D-glucopyranoside, sucrose and trehalose afforded nondializable, phosphorylated glycans in 6_??_34% yields. Polysucrose has a molecular weight of _??_9, 500. The synthetic glycans consist of carbohydrate (46_??_59%) and P (11.4_??_13.1%) and show reducing sugar values (5.0_??_30.8%). The alkaline hydrolysis of polysucrose was accompanied with a depolymerization and afforded sugar phosphates and oligosaccharides. The periodate oxidation gave formic acid (0.15_??_0.34 mole) and formaldehyde (0.07_??_0.17 mole/monosaccharide residue). The methylation study indicated their variously branched structures. 2, 3, 4, 6-Tetra-O-methyl-D-glucose was found in only 0.7_??_3.2% yields, and this is in agreement with their weak precipitation reactions with Con A. It is considered that the glycans are produced from nonreducing mono- and oligosaccharides by dehydration, transglycosidation and esterification with phosphate.
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