Synthesis of deoxy phosphatidylinositol analogues and phosphonate isosters of Ins(1,4,5)P3

Autor:	Jeannine Cleophax, Guillaume Prestat, Mauro V. de Almeida, Alice Gateau-Olesker, Didier Dubreuil, Stephane D. Gero
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry Cyclohexanone Phosphate Cleavage (embryo) Biochemistry Phosphonate chemistry.chemical_compound Enzyme chemistry Polyol Drug Discovery Alkyl substitution Phosphatidylinositol
Zdroj:	Tetrahedron. 55:12997-13010
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(99)00793-0
Popis:	The synthesis of phosphatidylinositol analogues, 6-deoxy Ins 1-(1,2-di- O -palmitoyl- sn -glycero)phosphate and 4,5-bisphosphate derivatives is presented. Two series of phosphonate isosters, 6-deoxy Ins(1)-butylphosphonate and 6-deoxy Ins(1)- C -methylenephosphonate as well as its 4,5-bisphosphate analogue were also prepared. All phosphoinositide analogues were obtained from cyclohexanone polyol derived from the d -galactose. Modification of charge distribution at position 1 of PtdIns and InsP derivatives, by replacement of a POH group by an alkyl substitution or a PC bond, resistant to cleavage by lipases, could induce inhibition of activity at further strategic enzymatic levels of the inositide cascade.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3abeed9ba08262d4c96204c7d7e36c6a https://doi.org/10.1016/s0040-4020(99)00793-0 Zobrazit plný text záznamu Full Text from ScienceDirect