Practical syntheses of 4-fluoroprolines

Practical syntheses of 4-fluoroprolines

Routes have been developed for the economical, process-scale synthesis of the 2 S,4 R, 2 S,4 S, and 2 R,4 S diastereomers of 4-fluoroproline. ▪ 4-Fluoroprolines are among the most useful nonnatural amino acids in chemical biology. Here, practical routes are reported for the synthesis of the 2 S,4 R,...

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Veröffentlicht in:Journal of fluorine chemistry 2008-09, Vol.129 (9), p.781-784
Hauptverfasser: Chorghade, Mukund S., Mohapatra, Debendra K., Sahoo, Gokarneswar, Gurjar, Mukund K., Mandlecha, Manish V., Bhoite, Nitin, Moghe, Santosh, Raines, Ronald T.
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Sprache:eng
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4-Fluoroproline
4-Hydroxyproline
Collagen
Nonnatural amino acid
Process-scale synthesis
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container_end_page 784
container_issue 9
container_start_page 781
container_title Journal of fluorine chemistry
container_volume 129
creator Chorghade, Mukund S.
Mohapatra, Debendra K.
Sahoo, Gokarneswar
Gurjar, Mukund K.
Mandlecha, Manish V.
Bhoite, Nitin
Moghe, Santosh
Raines, Ronald T.
description Routes have been developed for the economical, process-scale synthesis of the 2 S,4 R, 2 S,4 S, and 2 R,4 S diastereomers of 4-fluoroproline. ▪ 4-Fluoroprolines are among the most useful nonnatural amino acids in chemical biology. Here, practical routes are reported for the synthesis of the 2 S,4 R, 2 S,4 S, and 2 R,4 S diastereomers of 4-fluoroproline. Each route starts with (2 S,4 R)-4-hydroxyproline, which is a prevalent component of collagen and hence readily available, and uses a fluoride salt to install the fluoro group. Hence, the routes provide process-scale access to these useful nonnatural amino acids.
doi_str_mv 10.1016/j.jfluchem.2008.06.024
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source ScienceDirect Journals (5 years ago - present)
subjects 4-Fluoroproline
4-Hydroxyproline
Collagen
Nonnatural amino acid
Process-scale synthesis
title Practical syntheses of 4-fluoroprolines
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