Catalysis and acceleration of acyl transfer by aminocyclodextrins: A biomimetic system of use in enzyme modeling and drug design

Colin G. Ferguson; Gregory R.J. Thatcher

doi:10.1021/ol9906211

Catalysis and acceleration of acyl transfer by aminocyclodextrins: A biomimetic system of use in enzyme modeling and drug design

Colin G. Ferguson, Gregory R.J. Thatcher

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

15 Scopus citations

Abstract

(equation presented) Aminocyclodextrins (ACDs), perfunctionalized at the 6-position with amino groups, bind phosphonoformate (PFA) diesters and accelerate acyl transfer reactions with high efficiency at neutral pH. Aminolysis and esterolysis are accelerated and hydrolysis of PFA diesters is catalyzed by ACDs. PFA diesters have significant antiviral activity. The rapid reactions observed with ACDs show that biological nucleophiles may undergo facile covalent modification by PFA esters at physiological pH, which has significant implications for prodrug and drug design strategies.

Original language	English (US)
Pages (from-to)	829-832
Number of pages	4
Journal	Organic Letters
Volume	1
Issue number	6
DOIs	https://doi.org/10.1021/ol9906211
State	Published - Sep 23 1999
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol9906211

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title = "Catalysis and acceleration of acyl transfer by aminocyclodextrins: A biomimetic system of use in enzyme modeling and drug design",

abstract = "(equation presented) Aminocyclodextrins (ACDs), perfunctionalized at the 6-position with amino groups, bind phosphonoformate (PFA) diesters and accelerate acyl transfer reactions with high efficiency at neutral pH. Aminolysis and esterolysis are accelerated and hydrolysis of PFA diesters is catalyzed by ACDs. PFA diesters have significant antiviral activity. The rapid reactions observed with ACDs show that biological nucleophiles may undergo facile covalent modification by PFA esters at physiological pH, which has significant implications for prodrug and drug design strategies.",

author = "Ferguson, {Colin G.} and Thatcher, {Gregory R.J.}",

year = "1999",

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doi = "10.1021/ol9906211",

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T2 - A biomimetic system of use in enzyme modeling and drug design

AU - Ferguson, Colin G.

AU - Thatcher, Gregory R.J.

PY - 1999/9/23

Y1 - 1999/9/23

N2 - (equation presented) Aminocyclodextrins (ACDs), perfunctionalized at the 6-position with amino groups, bind phosphonoformate (PFA) diesters and accelerate acyl transfer reactions with high efficiency at neutral pH. Aminolysis and esterolysis are accelerated and hydrolysis of PFA diesters is catalyzed by ACDs. PFA diesters have significant antiviral activity. The rapid reactions observed with ACDs show that biological nucleophiles may undergo facile covalent modification by PFA esters at physiological pH, which has significant implications for prodrug and drug design strategies.

AB - (equation presented) Aminocyclodextrins (ACDs), perfunctionalized at the 6-position with amino groups, bind phosphonoformate (PFA) diesters and accelerate acyl transfer reactions with high efficiency at neutral pH. Aminolysis and esterolysis are accelerated and hydrolysis of PFA diesters is catalyzed by ACDs. PFA diesters have significant antiviral activity. The rapid reactions observed with ACDs show that biological nucleophiles may undergo facile covalent modification by PFA esters at physiological pH, which has significant implications for prodrug and drug design strategies.

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Catalysis and acceleration of acyl transfer by aminocyclodextrins: A biomimetic system of use in enzyme modeling and drug design

Abstract

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