Synthetic Routes to 3,4,5-Trihydroxypiperidines via Stereoselective and Biocatalysed Protocols, and Strategies to N- and O-Derivatisation

Kate L. Prichard; Nicholas O'Brien; Mahdi Ghorbani; Adam Wood; Evan Barnes; Atsushi Kato; Todd A. Houston; Michela I. Simone

doi:10.1002/ejoc.201801011

Synthetic Routes to 3,4,5-Trihydroxypiperidines via Stereoselective and Biocatalysed Protocols, and Strategies to N- and O-Derivatisation

Kate L. Prichard, Nicholas O'Brien, Mahdi Ghorbani, Adam Wood, Evan Barnes, Atsushi Kato, Todd A. Houston, Michela I. Simone^*

^*Corresponding author for this work

Hospital Pharmacy

Research output: Contribution to journal › Review article › peer-review

9 Scopus citations

Abstract

Stereoselective and biocatalysed synthetic routes to 3,4,5-trihydroxypiperidines and their N- and O-derivatisations are reviewed. These iminosugars effectively modulate glycosidase enzymes and display biological activities in immunosuppression, as anti-inflammatory agents and as anti-viral agents. Syntheses to these building blocks and their N- and O-derivatives are predicted to produce drug leads of high Fsp³ index. This is also crucial in the collection of structure-activity relationship data, particularly for diseases dependant on glycosidase modulation.

Original language	English
Pages (from-to)	6830-6842
Number of pages	13
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	48
DOIs	https://doi.org/10.1002/ejoc.201801011
State	Published - 2018/12/31

Keywords

3,4,5-Trihydroxypiperidine
Biocatalysis
Glycosidase
Iminosugar
Stereoselectivity

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201801011

Cite this

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title = "Synthetic Routes to 3,4,5-Trihydroxypiperidines via Stereoselective and Biocatalysed Protocols, and Strategies to N- and O-Derivatisation",

abstract = "Stereoselective and biocatalysed synthetic routes to 3,4,5-trihydroxypiperidines and their N- and O-derivatisations are reviewed. These iminosugars effectively modulate glycosidase enzymes and display biological activities in immunosuppression, as anti-inflammatory agents and as anti-viral agents. Syntheses to these building blocks and their N- and O-derivatives are predicted to produce drug leads of high Fsp3 index. This is also crucial in the collection of structure-activity relationship data, particularly for diseases dependant on glycosidase modulation.",

keywords = "3,4,5-Trihydroxypiperidine, Biocatalysis, Glycosidase, Iminosugar, Stereoselectivity",

author = "Prichard, {Kate L.} and Nicholas O'Brien and Mahdi Ghorbani and Adam Wood and Evan Barnes and Atsushi Kato and Houston, {Todd A.} and Simone, {Michela I.}",

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year = "2018",

month = dec,

day = "31",

doi = "10.1002/ejoc.201801011",

language = "英語",

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journal = "European Journal of Organic Chemistry",

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T1 - Synthetic Routes to 3,4,5-Trihydroxypiperidines via Stereoselective and Biocatalysed Protocols, and Strategies to N- and O-Derivatisation

AU - Prichard, Kate L.

AU - O'Brien, Nicholas

AU - Ghorbani, Mahdi

AU - Wood, Adam

AU - Barnes, Evan

AU - Kato, Atsushi

AU - Houston, Todd A.

AU - Simone, Michela I.

PY - 2018/12/31

Y1 - 2018/12/31

N2 - Stereoselective and biocatalysed synthetic routes to 3,4,5-trihydroxypiperidines and their N- and O-derivatisations are reviewed. These iminosugars effectively modulate glycosidase enzymes and display biological activities in immunosuppression, as anti-inflammatory agents and as anti-viral agents. Syntheses to these building blocks and their N- and O-derivatives are predicted to produce drug leads of high Fsp3 index. This is also crucial in the collection of structure-activity relationship data, particularly for diseases dependant on glycosidase modulation.

AB - Stereoselective and biocatalysed synthetic routes to 3,4,5-trihydroxypiperidines and their N- and O-derivatisations are reviewed. These iminosugars effectively modulate glycosidase enzymes and display biological activities in immunosuppression, as anti-inflammatory agents and as anti-viral agents. Syntheses to these building blocks and their N- and O-derivatives are predicted to produce drug leads of high Fsp3 index. This is also crucial in the collection of structure-activity relationship data, particularly for diseases dependant on glycosidase modulation.

KW - 3,4,5-Trihydroxypiperidine

KW - Biocatalysis

KW - Glycosidase

KW - Iminosugar

KW - Stereoselectivity

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U2 - 10.1002/ejoc.201801011

DO - 10.1002/ejoc.201801011

M3 - 総説

AN - SCOPUS:85057310601

SN - 1434-193X

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

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Synthetic Routes to 3,4,5-Trihydroxypiperidines via Stereoselective and Biocatalysed Protocols, and Strategies to N- and O-Derivatisation

Abstract

Keywords

ASJC Scopus subject areas

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