NDLI: Synthetic Route to Glycosyl β-1C-(phosphino)-phosphonates as Unprecedented Stable Glycosyl Diphosphate Analogs and Their Preliminary Biological Evaluation

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Synthetic Route to Glycosyl β-1C-(phosphino)-phosphonates as Unprecedented Stable Glycosyl Diphosphate Analogs and Their Preliminary Biological Evaluation

Content Provider	MDPI
Author	Bosco, Michaël Paik, Su-Jin Busca, Patricia Moore, Stuart Gravier-Pelletier, Christine
Copyright Year	2020
Description	The synthesis of glycosyl-β-1C-(phosphino)-phosphonates is a challenge since it has not yet been described. In this paper, we report an innovative synthetic method for their preparation from Glc-, Man-, and GlcNAc- lactone derivatives. The proposed original strategy involves the addition of the corresponding d-hexonolactones onto the dianion of (methylphosphino) phosphonate as a key step, followed by dehydration and stereoselective addition of dihydrogen on the resulting double bond. Final deprotection provides the new glycosyl diphosphate analogs in 35%, 36%, and 10% yield over 6 steps from the corresponding d-hexonolactones. The synthetized compounds were evaluated as inhibitors of phosphatase and diphosphatase activities and found to have complex concentration-dependent activatory and inhibitory properties on alkaline phosphatase. The synthetized tools should be useful to study other enzymes such as transferases.
Starting Page	4969
e-ISSN	14203049
DOI	10.3390/molecules25214969
Journal	Molecules
Issue Number	21
Volume Number	25
Language	English
Publisher	MDPI
Publisher Date	2020-10-27
Access Restriction	Open
Subject Keyword	Molecules Organic Chemistry C-glycoside Diphosphate Analogs Phosphinophosphonate Alkaline Diphosphatase Glycochemistry
Content Type	Text
Resource Type	Article

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