Stereoselective synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses

Yimin Zhu; John Ralph

doi:10.1016/j.tetlet.2011.05.038

Stereoselective synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses

Yimin Zhu, John Ralph

Division of Mathematics & Natural Sciences (Altoona)

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

18 Scopus citations

Abstract

1-O-β-Feruloyl and 1-O-β-sinapoyl glucopyranoses are two common substrates for serine carboxypeptidase-like acyltransferases and serve as acyl donors in the biosynthesis of numerous secondary metabolites. In addition, they are involved in plant cell wall cross-linking and are also ideal substrates for studying the kinetics of lignification involving hydroxycinnamates. We report the first chemical (and multi-gram scale) synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses.

Original language	English (US)
Pages (from-to)	3729-3731
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2011.05.038
State	Published - Jul 20 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.05.038

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title = "Stereoselective synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses",

abstract = "1-O-β-Feruloyl and 1-O-β-sinapoyl glucopyranoses are two common substrates for serine carboxypeptidase-like acyltransferases and serve as acyl donors in the biosynthesis of numerous secondary metabolites. In addition, they are involved in plant cell wall cross-linking and are also ideal substrates for studying the kinetics of lignification involving hydroxycinnamates. We report the first chemical (and multi-gram scale) synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses.",

author = "Yimin Zhu and John Ralph",

note = "Funding Information: We are grateful to the Stanford Global Climate and Energy Project, the DOE Great Lakes Bioenergy Research Center (DOE Office of Science BER DE-FC02-07ER64494), and the Department of Biochemistry, University of Wisconsin-Madison for support of this research. ",

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T1 - Stereoselective synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses

AU - Zhu, Yimin

AU - Ralph, John

N1 - Funding Information: We are grateful to the Stanford Global Climate and Energy Project, the DOE Great Lakes Bioenergy Research Center (DOE Office of Science BER DE-FC02-07ER64494), and the Department of Biochemistry, University of Wisconsin-Madison for support of this research.

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N2 - 1-O-β-Feruloyl and 1-O-β-sinapoyl glucopyranoses are two common substrates for serine carboxypeptidase-like acyltransferases and serve as acyl donors in the biosynthesis of numerous secondary metabolites. In addition, they are involved in plant cell wall cross-linking and are also ideal substrates for studying the kinetics of lignification involving hydroxycinnamates. We report the first chemical (and multi-gram scale) synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses.

AB - 1-O-β-Feruloyl and 1-O-β-sinapoyl glucopyranoses are two common substrates for serine carboxypeptidase-like acyltransferases and serve as acyl donors in the biosynthesis of numerous secondary metabolites. In addition, they are involved in plant cell wall cross-linking and are also ideal substrates for studying the kinetics of lignification involving hydroxycinnamates. We report the first chemical (and multi-gram scale) synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses.

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Stereoselective synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses

Abstract

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