Carboxypeptidase A-catalyzed direct conversion of leukotriene C4 to leukotriene F4
Leukotrienes (LTs) are 5-lipoxygenase (5-LO)-derived arachidonic metabolites that constitute a potent set of lipid mediators produced by inflammatory cells. Leukotriene A(4), a labile allylic epoxide formed from arachidonic acid by dual 5-LO activity, is the precursor for LTB(4) and LTC(4) synthesis...
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| Veröffentlicht in: | Archives of biochemistry and biophysics 2003-05, Vol.413 (2), p.158-163 |
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| creator | Reddanna, Pallu Prabhu, K Sandeep Whelan, Jay Reddy, C Channa |
| description | Leukotrienes (LTs) are 5-lipoxygenase (5-LO)-derived arachidonic metabolites that constitute a potent set of lipid mediators produced by inflammatory cells. Leukotriene A(4), a labile allylic epoxide formed from arachidonic acid by dual 5-LO activity, is the precursor for LTB(4) and LTC(4) synthesis. LTC(4) is further transformed enzymatically by the sequential action of gamma-glutamyltranspeptidase and dipeptidase to LTD(4) and LTE(4), respectively. In this report, we present evidence that bovine pancreatic carboxypeptidase A (CPA), which shares significant sequence homology with CPA in mast cell granules, catalyzes the conversion of LTC(4) to LTF(4) via the hydrolysis of an amide bond. The identity of CPA-catalyzed LTC(4) hydrolysis product as LTF(4) was confirmed by several analytical criteria, including enzymatic conversion to conjugated tetraene by soybean LO, conversion to LTE(4) by gamma-glutamyltranspeptidase, cochromatography with the standard LTF(4) and positive-ion fast-atom bombardment mass spectral analysis. Thus, it appears that the physiological significance of this single-step transformation may point toward a major cellular homeostatic mechanism of metabolizing LTC(4), a potent bronco- and vasoconstrictor, to a less potent form of cysteinyl LTs. |
| doi_str_mv | 10.1016/S0003-9861(03)00080-8 |
| format | Article |
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Leukotriene A(4), a labile allylic epoxide formed from arachidonic acid by dual 5-LO activity, is the precursor for LTB(4) and LTC(4) synthesis. LTC(4) is further transformed enzymatically by the sequential action of gamma-glutamyltranspeptidase and dipeptidase to LTD(4) and LTE(4), respectively. In this report, we present evidence that bovine pancreatic carboxypeptidase A (CPA), which shares significant sequence homology with CPA in mast cell granules, catalyzes the conversion of LTC(4) to LTF(4) via the hydrolysis of an amide bond. The identity of CPA-catalyzed LTC(4) hydrolysis product as LTF(4) was confirmed by several analytical criteria, including enzymatic conversion to conjugated tetraene by soybean LO, conversion to LTE(4) by gamma-glutamyltranspeptidase, cochromatography with the standard LTF(4) and positive-ion fast-atom bombardment mass spectral analysis. 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Leukotriene A(4), a labile allylic epoxide formed from arachidonic acid by dual 5-LO activity, is the precursor for LTB(4) and LTC(4) synthesis. LTC(4) is further transformed enzymatically by the sequential action of gamma-glutamyltranspeptidase and dipeptidase to LTD(4) and LTE(4), respectively. In this report, we present evidence that bovine pancreatic carboxypeptidase A (CPA), which shares significant sequence homology with CPA in mast cell granules, catalyzes the conversion of LTC(4) to LTF(4) via the hydrolysis of an amide bond. The identity of CPA-catalyzed LTC(4) hydrolysis product as LTF(4) was confirmed by several analytical criteria, including enzymatic conversion to conjugated tetraene by soybean LO, conversion to LTE(4) by gamma-glutamyltranspeptidase, cochromatography with the standard LTF(4) and positive-ion fast-atom bombardment mass spectral analysis. Thus, it appears that the physiological significance of this single-step transformation may point toward a major cellular homeostatic mechanism of metabolizing LTC(4), a potent bronco- and vasoconstrictor, to a less potent form of cysteinyl LTs.</description><subject>Amino Acids - metabolism</subject><subject>Animals</subject><subject>Arachidonate 5-Lipoxygenase - metabolism</subject><subject>Carboxypeptidases - pharmacology</subject><subject>Carboxypeptidases A</subject><subject>Cations</subject><subject>Cattle</subject><subject>Chromatography, High Pressure Liquid</subject><subject>gamma-Glutamyltransferase - metabolism</subject><subject>Hydrolysis</subject><subject>Leukotriene C4 - metabolism</subject><subject>Mass Spectrometry</subject><subject>Models, Chemical</subject><subject>SRS-A - analogs & derivatives</subject><subject>SRS-A - metabolism</subject><subject>Swine</subject><subject>Time Factors</subject><subject>Zinc - metabolism</subject><issn>0003-9861</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpVkElLxEAQhfugOOPoT1ByEj1Eq5cscxyCo8KA4HJueqlANJOO3YkYf72ZBcXTq3q8VwUfIWcUrinQ9OYZAHg8z1N6CfxqXHKI8wMy_bUn5DiENwBKRcqOyISyjM1TyqbkqVBeu6-hxbarrAoYLWKjOlUP32gjW3k0XWRc84k-VK6JXBnV2L-7zlfYYFSIqHP_nKU4IYelqgOe7nVGXpe3L8V9vHq8eygWq9gwBl3MMhRCJyYtlVECBdcGRAKMpaWwJQgch5wZrRNr0RjKONOpEHOdJJBYnvEZudjdbb376DF0cl0Fg3WtGnR9kBlnYizwMZjsgsa7EDyWsvXVWvlBUpAbgHILUG5IyVG3AGU-9s73D3q9RvvX2tPjP08VbjM</recordid><startdate>20030515</startdate><enddate>20030515</enddate><creator>Reddanna, Pallu</creator><creator>Prabhu, K Sandeep</creator><creator>Whelan, Jay</creator><creator>Reddy, C Channa</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20030515</creationdate><title>Carboxypeptidase A-catalyzed direct conversion of leukotriene C4 to leukotriene F4</title><author>Reddanna, Pallu ; Prabhu, K Sandeep ; Whelan, Jay ; Reddy, C Channa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c220t-27e44b5c6faca4e43bc0450226f4df04e26f82cbb5ddecc1232b6449b5505d373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Amino Acids - metabolism</topic><topic>Animals</topic><topic>Arachidonate 5-Lipoxygenase - metabolism</topic><topic>Carboxypeptidases - pharmacology</topic><topic>Carboxypeptidases A</topic><topic>Cations</topic><topic>Cattle</topic><topic>Chromatography, High Pressure Liquid</topic><topic>gamma-Glutamyltransferase - metabolism</topic><topic>Hydrolysis</topic><topic>Leukotriene C4 - metabolism</topic><topic>Mass Spectrometry</topic><topic>Models, Chemical</topic><topic>SRS-A - analogs & derivatives</topic><topic>SRS-A - metabolism</topic><topic>Swine</topic><topic>Time Factors</topic><topic>Zinc - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Reddanna, Pallu</creatorcontrib><creatorcontrib>Prabhu, K Sandeep</creatorcontrib><creatorcontrib>Whelan, Jay</creatorcontrib><creatorcontrib>Reddy, C Channa</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Archives of biochemistry and biophysics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Reddanna, Pallu</au><au>Prabhu, K Sandeep</au><au>Whelan, Jay</au><au>Reddy, C Channa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Carboxypeptidase A-catalyzed direct conversion of leukotriene C4 to leukotriene F4</atitle><jtitle>Archives of biochemistry and biophysics</jtitle><addtitle>Arch Biochem Biophys</addtitle><date>2003-05-15</date><risdate>2003</risdate><volume>413</volume><issue>2</issue><spage>158</spage><epage>163</epage><pages>158-163</pages><issn>0003-9861</issn><abstract>Leukotrienes (LTs) are 5-lipoxygenase (5-LO)-derived arachidonic metabolites that constitute a potent set of lipid mediators produced by inflammatory cells. Leukotriene A(4), a labile allylic epoxide formed from arachidonic acid by dual 5-LO activity, is the precursor for LTB(4) and LTC(4) synthesis. LTC(4) is further transformed enzymatically by the sequential action of gamma-glutamyltranspeptidase and dipeptidase to LTD(4) and LTE(4), respectively. In this report, we present evidence that bovine pancreatic carboxypeptidase A (CPA), which shares significant sequence homology with CPA in mast cell granules, catalyzes the conversion of LTC(4) to LTF(4) via the hydrolysis of an amide bond. The identity of CPA-catalyzed LTC(4) hydrolysis product as LTF(4) was confirmed by several analytical criteria, including enzymatic conversion to conjugated tetraene by soybean LO, conversion to LTE(4) by gamma-glutamyltranspeptidase, cochromatography with the standard LTF(4) and positive-ion fast-atom bombardment mass spectral analysis. Thus, it appears that the physiological significance of this single-step transformation may point toward a major cellular homeostatic mechanism of metabolizing LTC(4), a potent bronco- and vasoconstrictor, to a less potent form of cysteinyl LTs.</abstract><cop>United States</cop><pmid>12729612</pmid><doi>10.1016/S0003-9861(03)00080-8</doi><tpages>6</tpages></addata></record> |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Amino Acids - metabolism Animals Arachidonate 5-Lipoxygenase - metabolism Carboxypeptidases - pharmacology Carboxypeptidases A Cations Cattle Chromatography, High Pressure Liquid gamma-Glutamyltransferase - metabolism Hydrolysis Leukotriene C4 - metabolism Mass Spectrometry Models, Chemical SRS-A - analogs & derivatives SRS-A - metabolism Swine Time Factors Zinc - metabolism |
| title | Carboxypeptidase A-catalyzed direct conversion of leukotriene C4 to leukotriene F4 |
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