Parallel synthesis of an ester library for substrate mapping of esterases and lipases

Krista L. Morley; Vladimir P. Magloire; Christine Guérard; Romas J. Kazlauskas

doi:10.1016/j.tetasy.2004.07.048

Parallel synthesis of an ester library for substrate mapping of esterases and lipases

Krista L. Morley
, Vladimir P. Magloire
, Christine Guérard
, Romas J. Kazlauskas

Biochemistry, Molecular Biology, and Biophysics (CBS)

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

4 Scopus citations

Abstract

Use of solid-supported reagents simplified routine acylation of primary and secondary alcohols because it eliminated traditional purification. Using a parallel synthesizer, eight primary or secondary alcohols reacted with acid chloride in the presence of poly(4-vinylpyridine), which acted as a base and acylation catalyst. Filtration, subsequent addition of amino-functionalized silica gel to remove excess acid chloride and a second filtration affording the corresponding esters in high yield (70-98%), excellent chemical purity (93-99%). Acylation of enantiopure alcohols yielded enantiopure esters. Acylation of two tertiary alcohols gave esters in low yield (27-57%) and variable chemical purity (57-99%).

Original language	English (US)
Pages (from-to)	3005-3009
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	15
Issue number	18
DOIs	https://doi.org/10.1016/j.tetasy.2004.07.048
State	Published - Sep 20 2004

Bibliographical note

Funding Information:
We thank NSERC (Canada) for financial support and a postgraduate scholarship to K.L.M., Dr. Robert Zamboni (Merck Frosst, Montréal) for the loan of Argonaut Quest 210 parallel synthesizer and Sarah McDermott and Candice Suter for preliminary experiments.

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abstract = "Use of solid-supported reagents simplified routine acylation of primary and secondary alcohols because it eliminated traditional purification. Using a parallel synthesizer, eight primary or secondary alcohols reacted with acid chloride in the presence of poly(4-vinylpyridine), which acted as a base and acylation catalyst. Filtration, subsequent addition of amino-functionalized silica gel to remove excess acid chloride and a second filtration affording the corresponding esters in high yield (70-98\%), excellent chemical purity (93-99\%). Acylation of enantiopure alcohols yielded enantiopure esters. Acylation of two tertiary alcohols gave esters in low yield (27-57\%) and variable chemical purity (57-99\%).",

author = "Morley, \{Krista L.\} and Magloire, \{Vladimir P.\} and Christine Gu{\'e}rard and Kazlauskas, \{Romas J.\}",

note = "Funding Information: We thank NSERC (Canada) for financial support and a postgraduate scholarship to K.L.M., Dr. Robert Zamboni (Merck Frosst, Montr{\'e}al) for the loan of Argonaut Quest 210 parallel synthesizer and Sarah McDermott and Candice Suter for preliminary experiments. ",

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AU - Morley, Krista L.

AU - Magloire, Vladimir P.

AU - Guérard, Christine

AU - Kazlauskas, Romas J.

N1 - Funding Information: We thank NSERC (Canada) for financial support and a postgraduate scholarship to K.L.M., Dr. Robert Zamboni (Merck Frosst, Montréal) for the loan of Argonaut Quest 210 parallel synthesizer and Sarah McDermott and Candice Suter for preliminary experiments.

PY - 2004/9/20

Y1 - 2004/9/20

N2 - Use of solid-supported reagents simplified routine acylation of primary and secondary alcohols because it eliminated traditional purification. Using a parallel synthesizer, eight primary or secondary alcohols reacted with acid chloride in the presence of poly(4-vinylpyridine), which acted as a base and acylation catalyst. Filtration, subsequent addition of amino-functionalized silica gel to remove excess acid chloride and a second filtration affording the corresponding esters in high yield (70-98%), excellent chemical purity (93-99%). Acylation of enantiopure alcohols yielded enantiopure esters. Acylation of two tertiary alcohols gave esters in low yield (27-57%) and variable chemical purity (57-99%).

AB - Use of solid-supported reagents simplified routine acylation of primary and secondary alcohols because it eliminated traditional purification. Using a parallel synthesizer, eight primary or secondary alcohols reacted with acid chloride in the presence of poly(4-vinylpyridine), which acted as a base and acylation catalyst. Filtration, subsequent addition of amino-functionalized silica gel to remove excess acid chloride and a second filtration affording the corresponding esters in high yield (70-98%), excellent chemical purity (93-99%). Acylation of enantiopure alcohols yielded enantiopure esters. Acylation of two tertiary alcohols gave esters in low yield (27-57%) and variable chemical purity (57-99%).

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Parallel synthesis of an ester library for substrate mapping of esterases and lipases

Abstract

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