Asymmetric phosphorylation through catalytic P(III) phosphoramidite transfer: enantioselective synthesis of D-myo-inositol-6-phosphate.

Abstract:

:Despite the ubiquitous use of phosphoramidite chemistry in the synthesis of biophosphates, catalytic asymmetric phosphoramidite transfer remains largely unexplored for phosphate ester synthesis. We have discovered that a tetrazole-functionalized peptide, in the presence of 10-Å molecular sieves, functions as an enantioselective catalyst for phosphite transfer. This chemistry in turn has been used as the key step in a streamlined synthesis of myo-inositol-6-phosphate. Mechanistic insights implicate phosphate as a directing group for a highly selective kinetic resolution of a protected inositol monophosphate. This work represents a distinct and efficient method for the selective catalytic phosphorylation of natural products.

authors

Jordan PA,Kayser-Bricker KJ,Miller SJ

doi

10.1073/pnas.1001111107

subject

Has Abstract

pub_date

2010-11-30 00:00:00

pages

20620-4

issue

48

eissn

0027-8424

issn

1091-6490

pii

1001111107

journal_volume

107

pub_type

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