Inhibitors of biotin biosynthesis as potential herbicides

Ayelet Nudelman; Dana Marcovici-Mizrahi; Abraham Nudelman; Dennis Flint; Vernon Wittenbach

doi:10.1016/j.tet.2003.12.047

Inhibitors of biotin biosynthesis as potential herbicides

Ayelet Nudelman, Dana Marcovici-Mizrahi, Abraham Nudelman, Dennis Flint, Vernon Wittenbach

Department of Chemistry

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

22 Scopus citations

Abstract

Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR₅₀ (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values <50 ppm are considered herbicidal. Other KAPA analogs where the terminal Me group was replaced by bulkier substituents such as Et, i-Pr and HOCH₂ showed moderate activity.

Original language	English
Pages (from-to)	1731-1748
Number of pages	18
Journal	Tetrahedron
Volume	60
Issue number	8
DOIs	https://doi.org/10.1016/j.tet.2003.12.047
State	Published - 16 Feb 2004

Bibliographical note

Funding Information:
Generous support for this work by the ‘Marcus Center for Pharmaceutical and Medicinal Chemistry’ and the ‘Bronia and Samuel Hacker Fund for Scientific Instrumentation’ at Bar Ilan University, are gratefully acknowledged.

Funding

Generous support for this work by the ‘Marcus Center for Pharmaceutical and Medicinal Chemistry’ and the ‘Bronia and Samuel Hacker Fund for Scientific Instrumentation’ at Bar Ilan University, are gratefully acknowledged.

Funders	Funder number
Bar Ilan University

Keywords

7,8-Diaminopelargonic acid (DAPA)
7-Keto-8-aminopelerginic acid (KAPA)
Biotin
Biotin vitamers
Desthiobiotin (DTB)
Enzyme inhibitors
Herbicides

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10.1016/j.tet.2003.12.047

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title = "Inhibitors of biotin biosynthesis as potential herbicides",

abstract = "Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR50 (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values <50 ppm are considered herbicidal. Other KAPA analogs where the terminal Me group was replaced by bulkier substituents such as Et, i-Pr and HOCH2 showed moderate activity.",

keywords = "7,8-Diaminopelargonic acid (DAPA), 7-Keto-8-aminopelerginic acid (KAPA), Biotin, Biotin vitamers, Desthiobiotin (DTB), Enzyme inhibitors, Herbicides",

author = "Ayelet Nudelman and Dana Marcovici-Mizrahi and Abraham Nudelman and Dennis Flint and Vernon Wittenbach",

note = "Funding Information: Generous support for this work by the {\textquoteleft}Marcus Center for Pharmaceutical and Medicinal Chemistry{\textquoteright} and the {\textquoteleft}Bronia and Samuel Hacker Fund for Scientific Instrumentation{\textquoteright} at Bar Ilan University, are gratefully acknowledged. ",

year = "2004",

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doi = "10.1016/j.tet.2003.12.047",

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T1 - Inhibitors of biotin biosynthesis as potential herbicides

AU - Nudelman, Ayelet

AU - Marcovici-Mizrahi, Dana

AU - Nudelman, Abraham

AU - Flint, Dennis

AU - Wittenbach, Vernon

N1 - Funding Information: Generous support for this work by the ‘Marcus Center for Pharmaceutical and Medicinal Chemistry’ and the ‘Bronia and Samuel Hacker Fund for Scientific Instrumentation’ at Bar Ilan University, are gratefully acknowledged.

PY - 2004/2/16

Y1 - 2004/2/16

N2 - Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR50 (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values <50 ppm are considered herbicidal. Other KAPA analogs where the terminal Me group was replaced by bulkier substituents such as Et, i-Pr and HOCH2 showed moderate activity.

AB - Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR50 (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values <50 ppm are considered herbicidal. Other KAPA analogs where the terminal Me group was replaced by bulkier substituents such as Et, i-Pr and HOCH2 showed moderate activity.

KW - 7,8-Diaminopelargonic acid (DAPA)

KW - 7-Keto-8-aminopelerginic acid (KAPA)

KW - Biotin

KW - Biotin vitamers

KW - Desthiobiotin (DTB)

KW - Enzyme inhibitors

KW - Herbicides

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SN - 0040-4020

VL - 60

SP - 1731

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JO - Tetrahedron

JF - Tetrahedron

IS - 8

ER -

Inhibitors of biotin biosynthesis as potential herbicides

Abstract

Bibliographical note

Funding

Keywords

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