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Synthesis and biological activities of (4,6-di-O-phosphonato-β-d-mannopyranosyl)-methylphosphonate as an analogue of 1l-myo-inositol 1,4,5-trisphosphate

✍ Scribed by Sung-Kee Chung; Sung-Hwan Moon

Publisher
Elsevier Science
Year
1994
Tongue
English
Weight
993 KB
Volume
260
Category
Article
ISSN
0008-6215

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✦ Synopsis

The synthesis of the (Y and p anomers of the title compound (1) was accomplished from o-mannose. In the key step, the phosphonate analogues of the mannopyranosyl phosphates were prepared by a direct Wadsworth-Emmons condensation of a protected mannose derivative (8) with tetraethyl methylenebisphosphonate under two-phase conditions. In vitro bioassays have shown that the /I anomer (la) is a potent inhibitor of Ins(1,4,5IP, 3-kinase and inhibits other enzymes.

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