Two-step enzymatic modification of solid-supported bergenin in aqueous and organic media

Umar Akbar; Dong Sik Shin; Elizabeth Schneider; Jonathan S. Dordick; Douglas S. Clark

doi:10.1016/j.tetlet.2009.12.119

Two-step enzymatic modification of solid-supported bergenin in aqueous and organic media

Umar Akbar, Dong Sik Shin, Elizabeth Schneider, Jonathan S. Dordick, Douglas S. Clark

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

5 Scopus citations

Abstract

The natural flavonoid bergenin was directly immobilized onto carboxylic acid-functionalized controlled pore glass (carboxy-CPG) at 95% yield. Immobilized bergenin was brominated via chloroperoxidase in aqueous solution and then transesterified with vinyl butyrate in diisopropyl ether by subtilisin carslberg (SC) extracted into the organic solvent via ion-pairing. Enzymatic cleavage of 7-bromo-4-butyrylbergenin from carboxy-CPG (9.6% final yield) was accomplished using lipase B (LipB) in an aqueous/organic mixture (90/10 v/v of water/acetonitrile), demonstrating the feasibility of solid-phase biocatalysis of a natural product in aqueous and non-aqueous media.

Original language	English
Pages (from-to)	1220-1225
Number of pages	6
Journal	Tetrahedron Letters
Volume	51
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2009.12.119
State	Published - 24 Feb 2010
Externally published	Yes

Keywords

Biocatalysis
Enzyme cleavage
Non-aqueous
Solid Phase

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10.1016/j.tetlet.2009.12.119

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title = "Two-step enzymatic modification of solid-supported bergenin in aqueous and organic media",

abstract = "The natural flavonoid bergenin was directly immobilized onto carboxylic acid-functionalized controlled pore glass (carboxy-CPG) at 95% yield. Immobilized bergenin was brominated via chloroperoxidase in aqueous solution and then transesterified with vinyl butyrate in diisopropyl ether by subtilisin carslberg (SC) extracted into the organic solvent via ion-pairing. Enzymatic cleavage of 7-bromo-4-butyrylbergenin from carboxy-CPG (9.6% final yield) was accomplished using lipase B (LipB) in an aqueous/organic mixture (90/10 v/v of water/acetonitrile), demonstrating the feasibility of solid-phase biocatalysis of a natural product in aqueous and non-aqueous media.",

keywords = "Biocatalysis, Enzyme cleavage, Non-aqueous, Solid Phase",

author = "Umar Akbar and Shin, {Dong Sik} and Elizabeth Schneider and Dordick, {Jonathan S.} and Clark, {Douglas S.}",

note = "Funding Information: This work was supported by the National Institutes of Health ( GM66712 ), by the National Science Foundation ( BES-0228145 ) and the Korea Research Foundation Grant funded by the Korean Government ( KRF-2007-357-D00057 ). The authors thank Prime Synthesis for custom synthesizing the 12–13 carbon spacer CPG as well as Peter McDermott, I-Fan Lin, Brandon Gan, and Vincent Chan for assistance in obtaining both chemical and enzymatic bergenin cleavage and hydrolysis data.",

year = "2010",

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doi = "10.1016/j.tetlet.2009.12.119",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Two-step enzymatic modification of solid-supported bergenin in aqueous and organic media

AU - Akbar, Umar

AU - Shin, Dong Sik

AU - Schneider, Elizabeth

AU - Dordick, Jonathan S.

AU - Clark, Douglas S.

N1 - Funding Information: This work was supported by the National Institutes of Health ( GM66712 ), by the National Science Foundation ( BES-0228145 ) and the Korea Research Foundation Grant funded by the Korean Government ( KRF-2007-357-D00057 ). The authors thank Prime Synthesis for custom synthesizing the 12–13 carbon spacer CPG as well as Peter McDermott, I-Fan Lin, Brandon Gan, and Vincent Chan for assistance in obtaining both chemical and enzymatic bergenin cleavage and hydrolysis data.

PY - 2010/2/24

Y1 - 2010/2/24

N2 - The natural flavonoid bergenin was directly immobilized onto carboxylic acid-functionalized controlled pore glass (carboxy-CPG) at 95% yield. Immobilized bergenin was brominated via chloroperoxidase in aqueous solution and then transesterified with vinyl butyrate in diisopropyl ether by subtilisin carslberg (SC) extracted into the organic solvent via ion-pairing. Enzymatic cleavage of 7-bromo-4-butyrylbergenin from carboxy-CPG (9.6% final yield) was accomplished using lipase B (LipB) in an aqueous/organic mixture (90/10 v/v of water/acetonitrile), demonstrating the feasibility of solid-phase biocatalysis of a natural product in aqueous and non-aqueous media.

AB - The natural flavonoid bergenin was directly immobilized onto carboxylic acid-functionalized controlled pore glass (carboxy-CPG) at 95% yield. Immobilized bergenin was brominated via chloroperoxidase in aqueous solution and then transesterified with vinyl butyrate in diisopropyl ether by subtilisin carslberg (SC) extracted into the organic solvent via ion-pairing. Enzymatic cleavage of 7-bromo-4-butyrylbergenin from carboxy-CPG (9.6% final yield) was accomplished using lipase B (LipB) in an aqueous/organic mixture (90/10 v/v of water/acetonitrile), demonstrating the feasibility of solid-phase biocatalysis of a natural product in aqueous and non-aqueous media.

KW - Biocatalysis

KW - Enzyme cleavage

KW - Non-aqueous

KW - Solid Phase

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U2 - 10.1016/j.tetlet.2009.12.119

DO - 10.1016/j.tetlet.2009.12.119

M3 - Article

AN - SCOPUS:74049153376

SN - 0040-4039

VL - 51

SP - 1220

EP - 1225

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Two-step enzymatic modification of solid-supported bergenin in aqueous and organic media

Abstract

Keywords

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