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Org Lett. 2009 Apr 2;11(7):1551-4. doi: 10.1021/ol900149x.

A scalable synthesis of the IP7 isomer, 5-PP-Ins(1,2,3,4,6)P5.

Author information

1
Department of Medicinal Chemistry, The University of Utah, 419 Wakara Way, Suite 205, Salt Lake City, Utah 84108-1257, USA.

Abstract

The phosphorylated inositol diphosphates, including the diphosphoinositol pentakisphosphate regioisomers, play critical roles in signal transduction and cellular regulation. In particular, the IP(7) isomer 5-PP-Ins(1,2,3,4,6)P(5) is implicated in a nonenzymatic phosphate transfer converting a protein serine phosphate residue to a serine diphosphate. A scalable, practical new synthesis of 5-PP-Ins(1,2,3,4,6)P(5) is described that also allows access to a variety of IP(7) and IP(8) regioisomers. The identity of the synthetic 5-PP-Ins(1,2,3,4,6)P(5) was validated using IP6K1 to catalyze the conversion of IP(7) + ADP to ATP + IP(6).

PMID:
19253999
PMCID:
PMC2727512
DOI:
10.1021/ol900149x
[Indexed for MEDLINE]
Free PMC Article

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