Synthesis, reactivity and applications of 1-fluoroalkyl carboxylates: novel synthetic substrates for esterases and lipases

Carl S Rye; Jonathan Bayldon Baell; Ian Philip Street

doi:10.1016/j.tet.2007.02.059

Synthesis, reactivity and applications of 1-fluoroalkyl carboxylates: novel synthetic substrates for esterases and lipases

Carl S Rye, Jonathan Bayldon Baell, Ian Philip Street

Research output: Contribution to journal › Article › Research › peer-review

8 Citations (Scopus)

Abstract

A series of 1-fluoroalkyl carboxylate derivatives was synthesised by reacting a carboxylic acid and a ketone or aldehyde with (diethylamino)sulfur trifluoride (DAST). The reactivity of these compounds towards the nucleophiles benzylamine and water was investigated. The hydrolysis of the 1-fluoroalkyl carboxylates by an esterase was observed, along with the concomitant release of the fluoride ion, demonstrating the potential for a new esterase assay platform. Other applications may include a detectable in situ inhibitor synthesis protocol.

Original language	English
Pages (from-to)	3306 - 3311
Number of pages	6
Journal	Tetrahedron
Volume	63
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2007.02.059
Publication status	Published - 2007
Externally published	Yes

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10.1016/j.tet.2007.02.059

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Cite this

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title = "Synthesis, reactivity and applications of 1-fluoroalkyl carboxylates: novel synthetic substrates for esterases and lipases",

abstract = "A series of 1-fluoroalkyl carboxylate derivatives was synthesised by reacting a carboxylic acid and a ketone or aldehyde with (diethylamino)sulfur trifluoride (DAST). The reactivity of these compounds towards the nucleophiles benzylamine and water was investigated. The hydrolysis of the 1-fluoroalkyl carboxylates by an esterase was observed, along with the concomitant release of the fluoride ion, demonstrating the potential for a new esterase assay platform. Other applications may include a detectable in situ inhibitor synthesis protocol.",

author = "Rye, {Carl S} and Baell, {Jonathan Bayldon} and Street, {Ian Philip}",

year = "2007",

doi = "10.1016/j.tet.2007.02.059",

language = "English",

volume = "63",

pages = "3306 -- 3311",

journal = "Tetrahedron",

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T1 - Synthesis, reactivity and applications of 1-fluoroalkyl carboxylates: novel synthetic substrates for esterases and lipases

AU - Rye, Carl S

AU - Baell, Jonathan Bayldon

AU - Street, Ian Philip

PY - 2007

Y1 - 2007

N2 - A series of 1-fluoroalkyl carboxylate derivatives was synthesised by reacting a carboxylic acid and a ketone or aldehyde with (diethylamino)sulfur trifluoride (DAST). The reactivity of these compounds towards the nucleophiles benzylamine and water was investigated. The hydrolysis of the 1-fluoroalkyl carboxylates by an esterase was observed, along with the concomitant release of the fluoride ion, demonstrating the potential for a new esterase assay platform. Other applications may include a detectable in situ inhibitor synthesis protocol.

AB - A series of 1-fluoroalkyl carboxylate derivatives was synthesised by reacting a carboxylic acid and a ketone or aldehyde with (diethylamino)sulfur trifluoride (DAST). The reactivity of these compounds towards the nucleophiles benzylamine and water was investigated. The hydrolysis of the 1-fluoroalkyl carboxylates by an esterase was observed, along with the concomitant release of the fluoride ion, demonstrating the potential for a new esterase assay platform. Other applications may include a detectable in situ inhibitor synthesis protocol.

UR - http://www.sciencedirect.com/science/article/pii/S0040402007002700

U2 - 10.1016/j.tet.2007.02.059

DO - 10.1016/j.tet.2007.02.059

M3 - Article

VL - 63

SP - 3306

EP - 3311

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 16

ER -