Inactivation of soybean sterol 24-C-methyltransferase by elongated sterol side chains at C26

Zhihong Song; W. David Nes

doi:10.1016/j.bmcl.2007.07.096

Inactivation of soybean sterol 24-C-methyltransferase by elongated sterol side chains at C26

Zhihong Song, W. David Nes

Chemistry and Biochemistry

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5 Scopus citations

Abstract

The enzymatic C-methylation reaction catalyzed by the Glycine max sterol 24-C-methyltransferase was studied with substrate analogs containing a cycloartenol nucleus (CA) and a double bond (8) or triple bond (14) attached to C26. The production of the corresponding C24(28)-methylene olefin and time-dependent inhibition kinetics of k_inact 0.24 min^-1 (CA-8) or 0.06 min^-1 (CA-14) indicates an active-site directed process and partitioning to produce novel products.

Original language	English
Pages (from-to)	5902-5906
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	17
Issue number	21
DOIs	https://doi.org/10.1016/j.bmcl.2007.07.096
State	Published - Nov 1 2007

Keywords

Cycloartenol
Mechanism-based inhibitor
Phytosterol
Sterol methylation
Sterol methyltransferase

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10.1016/j.bmcl.2007.07.096

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title = "Inactivation of soybean sterol 24-C-methyltransferase by elongated sterol side chains at C26",

abstract = "The enzymatic C-methylation reaction catalyzed by the Glycine max sterol 24-C-methyltransferase was studied with substrate analogs containing a cycloartenol nucleus (CA) and a double bond (8) or triple bond (14) attached to C26. The production of the corresponding C24(28)-methylene olefin and time-dependent inhibition kinetics of kinact 0.24 min-1 (CA-8) or 0.06 min-1 (CA-14) indicates an active-site directed process and partitioning to produce novel products.",

keywords = "Cycloartenol, Mechanism-based inhibitor, Phytosterol, Sterol methylation, Sterol methyltransferase",

author = "Zhihong Song and Nes, {W. David}",

note = "Funding Information: This work was supported by the National Science Foundation (MCB-0417436) and the Welch Foundation (D-1276). We thank Jialin Liu for the synthesis and purification of the test compounds. ",

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doi = "10.1016/j.bmcl.2007.07.096",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Inactivation of soybean sterol 24-C-methyltransferase by elongated sterol side chains at C26

AU - Song, Zhihong

AU - Nes, W. David

N1 - Funding Information: This work was supported by the National Science Foundation (MCB-0417436) and the Welch Foundation (D-1276). We thank Jialin Liu for the synthesis and purification of the test compounds.

PY - 2007/11/1

Y1 - 2007/11/1

N2 - The enzymatic C-methylation reaction catalyzed by the Glycine max sterol 24-C-methyltransferase was studied with substrate analogs containing a cycloartenol nucleus (CA) and a double bond (8) or triple bond (14) attached to C26. The production of the corresponding C24(28)-methylene olefin and time-dependent inhibition kinetics of kinact 0.24 min-1 (CA-8) or 0.06 min-1 (CA-14) indicates an active-site directed process and partitioning to produce novel products.

AB - The enzymatic C-methylation reaction catalyzed by the Glycine max sterol 24-C-methyltransferase was studied with substrate analogs containing a cycloartenol nucleus (CA) and a double bond (8) or triple bond (14) attached to C26. The production of the corresponding C24(28)-methylene olefin and time-dependent inhibition kinetics of kinact 0.24 min-1 (CA-8) or 0.06 min-1 (CA-14) indicates an active-site directed process and partitioning to produce novel products.

KW - Cycloartenol

KW - Mechanism-based inhibitor

KW - Phytosterol

KW - Sterol methylation

KW - Sterol methyltransferase

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U2 - 10.1016/j.bmcl.2007.07.096

DO - 10.1016/j.bmcl.2007.07.096

M3 - Article

C2 - 17851075

AN - SCOPUS:34548851972

SN - 0960-894X

VL - 17

SP - 5902

EP - 5906

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 21

ER -

Inactivation of soybean sterol 24-C-methyltransferase by elongated sterol side chains at C26

Abstract

Keywords

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