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Development of a solid phase synthesis strategy for soluble phosphoinositide analogues

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Chemical Science Vol - 3 Issue - 5

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Chemical Science Vol -1

Development of a solid phase synthesis strategy for soluble phosphoinositide analogues

Content Provider	Royal Society of Chemistry (RSC)
Author	Bru, Miriam Kotkar, Shriram P. Köhn, Maja Kar, Nilanjana
Copyright Year	2012
Abstract	Phosphatidyl inositol phosphates (PIPn) exist in nature with a variety of phosphorylation patterns on the inositol head group. These compounds are vital signaling molecules that regulate numerous key cellular processes. Different enzymes such as kinases and phosphatases modify the phosphorylation patterns. There are only a few structure activity relationship (SAR) studies with PIPn analogues to gather information for the development of PIPn analogue-based inhibitors, because chemical modifications of the inositol head group are very challenging and laborious due to multiple synthetic steps that often require tedious purifications. To simplify such studies, we describe here the development of the first solid phase organic synthesis (SPOS) strategy for PIPn analogues and derivatives providing the basis for the modification of the inositol head group in a combinatorial fashion. Our strategy builds for the first time on only four inositol building blocks to address the seven phosphorylation patterns, and this is enabled by a novel selective benzylidene acetal ring opening on a solid support, which is not possible in solution so far. The first structure–activity-relationship studies using PI(4,5)P2 analogues and derivatives with lipid phosphatases are presented.
Starting Page	1893
Ending Page	1902
Page Count	10
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	3
Issue Number	6
Journal	Chemical Science
DOI	10.1039/c2sc01061e
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Organic synthesis Acetal Phosphorylation Inositol Structure\u2013activity relationship Inositol phosphate Combinatorics Benzylidene compounds Phosphatidylinositol 4,5-bisphosphate Lipid
Content Type	Text
Resource Type	Article
Subject	Chemistry

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Development of a solid phase synthesis strategy for soluble phosphoinositide analogues

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Development of a solid phase synthesis strategy for soluble phosphoinositide analogues

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Development of a solid phase synthesis strategy for soluble phosphoinositide analogues