Synthesis and Kinase Phosphorylation of 4-Deoxy-D-threohexulose
Keyword(s):
Synthesis of the only unknown deoxyfructose, 4-deoxy-D-threohexulose, is reported. Its preparation involved reductive lithium aluminum hydride ring opening of 3,4-anhydro-1,2:5,6-di-O-isopropylidene- D-talitol, followed by hydrolysis of the resulting epimeric deoxy diisopropylidene hexitols and selective Acetobacter suboxydans oxidation of 3-deoxy-D-arabinohexitol. Kinetic studies using 4-deoxy-D-threohexulose as substrate for yeast hexokinase support the premise that the C-4 hydroxyl is a binding group in formation of the enzyme–substrate complex. Enzymatic synthesis of 4-deoxy-D-threohexulose 6-phosphate and 4-deoxy-D-threohexulose 1,6-diphosphate has been achieved in low yield from 4-deoxy-D-threohexulose.
1971 ◽
Vol 49
(20)
◽
pp. 3342-3347
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1973 ◽
Vol 18
(1)
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pp. 96-97
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Keyword(s):
1957 ◽
Vol 35
(10)
◽
pp. 1102-1108
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2016 ◽
Vol 15
(6)
◽
pp. 501-527
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