Investigation of Substrate Binding and Product Stereochemistry Issues in Two Linoleate 9-Lipoxygenases

Boeglin, William E.; Itoh, Aya; Zheng, Yuxiang; Coffa, Gianguido; Howe, Gregg A.; Brash, Alan R.

doi:10.1007/s11745-008-3230-1

Title: Investigation of Substrate Binding and Product Stereochemistry Issues in Two Linoleate 9-Lipoxygenases

Authors:

Boeglin, William E. ^[1]; Itoh, Aya ^[2]; Zheng, Yuxiang ^[1]; Coffa, Gianguido ^[3]; Howe, Gregg A. ^[4]; Brash, Alan R. ^[1]

, Department of Pharmacology, Vanderbilt University Medical Center, RRB Room 510, 23rd Ave at Pierce Nashville TN 37232-6602 USA
, MSU-DOE Plant Research Laboratory, Michigan State University, East Lansing MI 48824-1312 USA, , Institute for Advanced Biosciences, Keio University, Tsuruoka 997-0035 Japan
, Department of Pharmacology, Vanderbilt University Medical Center, RRB Room 510, 23rd Ave at Pierce Nashville TN 37232-6602 USA, Algenol Biofuels, Inc. 1700 Union Ave Suite A Baltimore MD 21211 USA
, MSU-DOE Plant Research Laboratory, Michigan State University, East Lansing MI 48824-1312 USA, , Department of Biochemistry and Molecular Biology, Michigan State University, East Lansing MI 48824-1312 USA

Publication Date:: Tue Sep 16 00:00:00 EDT 2008

Sponsoring Org.:: USDOE

OSTI Identifier:: 1464352

Grant/Contract Number:: FG02-91ER20021

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Lipids

Additional Journal Information:: Journal Name: Lipids Journal Volume: 43 Journal Issue: 11; Journal ID: ISSN 0024-4201

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: United States

Language:: English

Citation Formats


                    Boeglin, William E., Itoh, Aya, Zheng, Yuxiang, Coffa, Gianguido, Howe, Gregg A., and Brash, Alan R. Investigation of Substrate Binding and Product Stereochemistry Issues in Two Linoleate 9-Lipoxygenases.  United States: N. p., 2008. 
Web.  doi:10.1007/s11745-008-3230-1.

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                    Boeglin, William E., Itoh, Aya, Zheng, Yuxiang, Coffa, Gianguido, Howe, Gregg A., & Brash, Alan R. Investigation of Substrate Binding and Product Stereochemistry Issues in Two Linoleate 9-Lipoxygenases.  United States.  https://doi.org/10.1007/s11745-008-3230-1

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                    Boeglin, William E., Itoh, Aya, Zheng, Yuxiang, Coffa, Gianguido, Howe, Gregg A., and Brash, Alan R. Tue .  
"Investigation of Substrate Binding and Product Stereochemistry Issues in Two Linoleate 9-Lipoxygenases".  United States.  https://doi.org/10.1007/s11745-008-3230-1.

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@article{osti_1464352,

  title        = {Investigation of Substrate Binding and Product Stereochemistry Issues in Two Linoleate 9-Lipoxygenases},

  author       = {Boeglin, William E. and Itoh, Aya and Zheng, Yuxiang and Coffa, Gianguido and Howe, Gregg A. and Brash, Alan R.},

  abstractNote = {},

  doi          = {10.1007/s11745-008-3230-1},

  journal      = {Lipids},

  number       = 11,

  volume       = 43,

  place        = {United States},

  year         = {Tue Sep 16 00:00:00 EDT 2008},

  month        = {Tue Sep 16 00:00:00 EDT 2008}

}

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https://doi.org/10.1007/s11745-008-3230-1

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Works referenced in this record:

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Oxylipins Produced by the 9-Lipoxygenase Pathway in Arabidopsis Regulate Lateral Root Development and Defense Responses through a Specific Signaling Cascade
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Purification and Catalytic Activities of the Two Domains of the Allene Oxide Synthase-Lipoxygenase Fusion Protein of the Coral Plexaura homomalla
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A single active site residue directs oxygenation stereospecificity in lipoxygenases: Stereocontrol is linked to the position of oxygenation
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Plant Physiology, Vol. 136, Issue 1
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Enantiomeric Separation of Hydroxy and Hydroperoxy Eicosanoids by Chiral Column Chromatography
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Characterization of an Arabidopsis Lipoxygenase Gene Responsive to Methyl Jasmonate and Wounding
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The Cloning of Two Tomato Lipoxygenase Genes and Their Differential Expression during Fruit Ripening
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journal, December 2005

Coffa, Gianguido; Schneider, Claus; Brash, Alan R.
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Title: Investigation of Substrate Binding and Product Stereochemistry Issues in Two Linoleate 9-Lipoxygenases

Citation Formats

Expression, Purification, and Characterization of a Recombinant 5-Lipoxygenase from Potato Tuber journal, February 1998

An Arabidopsis thaliana Lipoxygenase Gene Can Be Induced by Pathogens, Abscisic Acid, and Methyl Jasmonate journal, February 1993

Enzyme-catalyzed and enzyme-triggered pathways in dioxygenation of 1-monolinoleoyl-rac-glycerol by potato tuber lipoxygenase journal, April 2001

Enzyme with dual lipoxygenase activities catalyzes leukotriene A4 synthesis from arachidonic acid. journal, February 1984

Oxygenation of phosphatidylcholine by human polymorphonuclear leukocyte 15-lipoxygenase journal, July 1985

Investigation of the oxygenation of phospholipids by the porcine leukocyte and human platelet arachidonate 12-lipoxygenases journal, November 1993

Control of Oxygenation in Lipoxygenase and Cyclooxygenase Catalysis journal, May 2007

11-Hydroperoxyeicosatetraenoic acid is the major dioxygenation product of lipoxygenase isolated from hairy root cultures of Solanum tuberosum journal, December 1992

Rabbit reticulocyte lipoxygenase catalyzes specific 12(S) and 15(S) oxygenation of arachidonoyl-phosphatidylcholine journal, September 1988

With Anandamide as Substrate Plant 5-Lipoxygenases Behave like 11-Lipoxygenases journal, July 1998

Soybean lipoxygenase-1 enzymically forms both (9S)- and (13S)-hydroperoxides from linoleic acid by a pH-dependent mechanism journal, February 1989

Specificity of two lipoxygenases from rice: Unusual regiospecificity of a lipoxygenase isoenzyme journal, August 1996

Oxylipins Produced by the 9-Lipoxygenase Pathway in Arabidopsis Regulate Lateral Root Development and Defense Responses through a Specific Signaling Cascade journal, March 2007

T HE L IPOXYGENASE P ATHWAY journal, June 2002

Stereospecificity of the hydrogen abstraction at carbon atom n-8 in the oxygenation of linoleic acid by lipoxygenases from corn germs and soya beans journal, September 1972

Bile salt-dependent oxygenation of polyunsaturated phosphatidylcholines by soybean lipoxygenase-1 journal, May 1983

A lipoxygenase in rabbit reticulocytes which attacks phospholipids and intact mitochondria journal, December 1975

Characterization of HETEs and related conjugated dienes by UV spectroscopy journal, April 1988

Purification and Catalytic Activities of the Two Domains of the Allene Oxide Synthase-Lipoxygenase Fusion Protein of the Coral Plexaura homomalla journal, November 1999

A simple method for the preparation of pure 9-d-hydroperoxide of linoleic acid and methyl linoleate based on the positional specificity of lipoxygenase in tomato fruit journal, March 1977

A single active site residue directs oxygenation stereospecificity in lipoxygenases: Stereocontrol is linked to the position of oxygenation journal, October 2004

Detection, assay, and isolation of allene oxide synthase book, January 1996

Identification of a Specific Isoform of Tomato Lipoxygenase (TomloxC) Involved in the Generation of Fatty Acid-Derived Flavor Compounds journal, September 2004

Enantiomeric Separation of Hydroxy and Hydroperoxy Eicosanoids by Chiral Column Chromatography book, January 2007

Oxylipin metabolism in response to stress journal, June 2002

On the Relationships of Substrate Orientation, Hydrogen Abstraction, and Product Stereochemistry in Single and Double Dioxygenations by Soybean Lipoxygenase-1 and Its Ala542Gly Mutant journal, September 2005

On the reaction specificity of the lipoxygenase from tomato fruits journal, January 1994

A Rapid Method of Total Lipid Extraction and Purification journal, January 1959

A Gene Encoding a Chloroplast-Targeted Lipoxygenase in Tomato Leaves Is Transiently Induced by Wounding, Systemin, and Methyl Jasmonate journal, July 1997

Analysis of a specific oxygenation reaction of soybean lipoxygenase-1 with fatty acids esterified in phospholipids journal, August 1987

Controlled synthesis of monohydroperoxides by α-tocopherol inhibited autoxidation of polyunsaturated lipids journal, February 1983

Enantiomeric Separation of Hydroxy Eicosanoids by Chiral Column Chromatography: Effect of the Alcohol Modifier journal, December 2000

Characterization of an Arabidopsis Lipoxygenase Gene Responsive to Methyl Jasmonate and Wounding journal, December 1993

The LOX1 Gene of Arabidopsis Is Temporally and Spatially Regulated in Germinating Seedlings journal, May 1994

The Cloning of Two Tomato Lipoxygenase Genes and Their Differential Expression during Fruit Ripening journal, September 1994

A comprehensive model of positional and stereo control in lipoxygenases journal, December 2005

Expression, Purification, and Characterization of a Recombinant 5-Lipoxygenase from Potato Tuber
journal, February 1998

An Arabidopsis thaliana Lipoxygenase Gene Can Be Induced by Pathogens, Abscisic Acid, and Methyl Jasmonate
journal, February 1993

Enzyme-catalyzed and enzyme-triggered pathways in dioxygenation of 1-monolinoleoyl-rac-glycerol by potato tuber lipoxygenase
journal, April 2001

Enzyme with dual lipoxygenase activities catalyzes leukotriene A4 synthesis from arachidonic acid.
journal, February 1984

Oxygenation of phosphatidylcholine by human polymorphonuclear leukocyte 15-lipoxygenase
journal, July 1985

Investigation of the oxygenation of phospholipids by the porcine leukocyte and human platelet arachidonate 12-lipoxygenases
journal, November 1993

Control of Oxygenation in Lipoxygenase and Cyclooxygenase Catalysis
journal, May 2007

11-Hydroperoxyeicosatetraenoic acid is the major dioxygenation product of lipoxygenase isolated from hairy root cultures of Solanum tuberosum
journal, December 1992

Rabbit reticulocyte lipoxygenase catalyzes specific 12(S) and 15(S) oxygenation of arachidonoyl-phosphatidylcholine
journal, September 1988

With Anandamide as Substrate Plant 5-Lipoxygenases Behave like 11-Lipoxygenases
journal, July 1998

Soybean lipoxygenase-1 enzymically forms both (9S)- and (13S)-hydroperoxides from linoleic acid by a pH-dependent mechanism
journal, February 1989

Specificity of two lipoxygenases from rice: Unusual regiospecificity of a lipoxygenase isoenzyme
journal, August 1996

Oxylipins Produced by the 9-Lipoxygenase Pathway in Arabidopsis Regulate Lateral Root Development and Defense Responses through a Specific Signaling Cascade
journal, March 2007

T HE L IPOXYGENASE P ATHWAY
journal, June 2002

Stereospecificity of the hydrogen abstraction at carbon atom n-8 in the oxygenation of linoleic acid by lipoxygenases from corn germs and soya beans
journal, September 1972

Bile salt-dependent oxygenation of polyunsaturated phosphatidylcholines by soybean lipoxygenase-1
journal, May 1983

A lipoxygenase in rabbit reticulocytes which attacks phospholipids and intact mitochondria
journal, December 1975

Characterization of HETEs and related conjugated dienes by UV spectroscopy
journal, April 1988

Purification and Catalytic Activities of the Two Domains of the Allene Oxide Synthase-Lipoxygenase Fusion Protein of the Coral Plexaura homomalla
journal, November 1999

A simple method for the preparation of pure 9-d-hydroperoxide of linoleic acid and methyl linoleate based on the positional specificity of lipoxygenase in tomato fruit
journal, March 1977

A single active site residue directs oxygenation stereospecificity in lipoxygenases: Stereocontrol is linked to the position of oxygenation
journal, October 2004

Detection, assay, and isolation of allene oxide synthase
book, January 1996

Identification of a Specific Isoform of Tomato Lipoxygenase (TomloxC) Involved in the Generation of Fatty Acid-Derived Flavor Compounds
journal, September 2004

Enantiomeric Separation of Hydroxy and Hydroperoxy Eicosanoids by Chiral Column Chromatography
book, January 2007

Oxylipin metabolism in response to stress
journal, June 2002

On the Relationships of Substrate Orientation, Hydrogen Abstraction, and Product Stereochemistry in Single and Double Dioxygenations by Soybean Lipoxygenase-1 and Its Ala542Gly Mutant
journal, September 2005

On the reaction specificity of the lipoxygenase from tomato fruits
journal, January 1994

A Rapid Method of Total Lipid Extraction and Purification
journal, January 1959

A Gene Encoding a Chloroplast-Targeted Lipoxygenase in Tomato Leaves Is Transiently Induced by Wounding, Systemin, and Methyl Jasmonate
journal, July 1997

Analysis of a specific oxygenation reaction of soybean lipoxygenase-1 with fatty acids esterified in phospholipids
journal, August 1987

Controlled synthesis of monohydroperoxides by α-tocopherol inhibited autoxidation of polyunsaturated lipids
journal, February 1983

Enantiomeric Separation of Hydroxy Eicosanoids by Chiral Column Chromatography: Effect of the Alcohol Modifier
journal, December 2000

Characterization of an Arabidopsis Lipoxygenase Gene Responsive to Methyl Jasmonate and Wounding
journal, December 1993

The LOX1 Gene of Arabidopsis Is Temporally and Spatially Regulated in Germinating Seedlings
journal, May 1994

The Cloning of Two Tomato Lipoxygenase Genes and Their Differential Expression during Fruit Ripening
journal, September 1994

A comprehensive model of positional and stereo control in lipoxygenases
journal, December 2005