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A Phosphoramidite Analogue of Cyclotriphosphate Enables Iterative Polyphosphorylations
Author(s) -
Singh Jyoti,
Steck Nicole,
De Debaditya,
Hofer Alexandre,
Ripp Alexander,
Captain Ilya,
Keller Manfred,
Wender Paul A.,
Bhandari Rashna,
Jessen Henning J.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201814366
Subject(s) - phosphoramidite , reagent , nucleophile , context (archaeology) , pyrophosphate , combinatorial chemistry , chemistry , iterative method , computer science , algorithm , organic chemistry , oligonucleotide , dna , paleontology , biochemistry , biology , enzyme , catalysis
An iterative polyphosphorylation approach is described, which is based on a phosphoramidite (P‐amidite) derived reagent ( c ‐PyPA) obtained from the cyclization of pyrophosphate with a reactive diisopropylaminodichlorophosphine. This type of reagent is unprecedented as it represents a reactive P‐amidite without protecting groups. The reagent proved to be stable in solution over several weeks. Its utility is described in the context of iterative monodirectional and bidirectional polyphosphorylations. The ensuing functionalized cyclotriphosphate can be opened with a variety of nucleophiles providing ready access to diverse functionalized polyphosphate chains of defined length with several tags, including both P‐N and P‐O labels. Their interaction with exo‐ and endopolyphosphatases is described.