Stereoisomeric bio-inversion key to biosynthesis of firefly d-luciferin
The chirality of the luciferin substrate is critical to the luciferin–luciferase reaction producing bioluminescence. In firefly, the biosynthetic pathway of d-luciferin is still unclear, although it can be synthesized in vitro from d-cysteine. Here, we show that the firefly produces both d- and l-lu...
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| Veröffentlicht in: | FEBS letters 2006-10, Vol.580 (22), p.5283-5287 |
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| creator | Niwa, Kazuki Nakamura, Mitsuhiro Ohmiya, Yoshihiro |
| description | The chirality of the luciferin substrate is critical to the luciferin–luciferase reaction producing bioluminescence. In firefly, the biosynthetic pathway of
d-luciferin is still unclear, although it can be synthesized in vitro from
d-cysteine. Here, we show that the firefly produces both
d- and
l-luciferin, and that the amount of active
d-luciferin increases gradually with maturation stage. Studies of firefly body extracts indicate the possible conversion of
l-cysteine via
l-luciferin into
d-luciferin, suggesting that the biosynthesis is enzymatically regulated by stereoisomeric bio-inversion of
l-luciferin. We conclude that the selection of chirality in living organisms is not as rigid as previously thought. |
| doi_str_mv | 10.1016/j.febslet.2006.08.073 |
| format | Article |
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d-luciferin is still unclear, although it can be synthesized in vitro from
d-cysteine. Here, we show that the firefly produces both
d- and
l-luciferin, and that the amount of active
d-luciferin increases gradually with maturation stage. Studies of firefly body extracts indicate the possible conversion of
l-cysteine via
l-luciferin into
d-luciferin, suggesting that the biosynthesis is enzymatically regulated by stereoisomeric bio-inversion of
l-luciferin. We conclude that the selection of chirality in living organisms is not as rigid as previously thought.</description><identifier>ISSN: 0014-5793</identifier><identifier>EISSN: 1873-3468</identifier><identifier>DOI: 10.1016/j.febslet.2006.08.073</identifier><identifier>PMID: 16979628</identifier><language>eng</language><publisher>England: Elsevier B.V</publisher><subject>2-cyano-6-hydroxybenzothiazole ; 4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole ; ABD-F ; Animals ; Bioluminescence ; Biosynthesis ; Bovine serum albumin ; BSA ; CHBT ; CoA ; coenzyme A ; Enantiomer ; Fireflies - chemistry ; Fireflies - growth & development ; Firefly ; Firefly Luciferin - chemistry ; Firefly Luciferin - metabolism ; Luciferase ; Luciferin ; Stereoisomerism ; TBP ; tri-n-butylphosphine</subject><ispartof>FEBS letters, 2006-10, Vol.580 (22), p.5283-5287</ispartof><rights>2006 Federation of European Biochemical Societies</rights><rights>FEBS Letters 580 (2006) 1873-3468 © 2015 Federation of European Biochemical Societies</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5723-739c73a821cfe595b5da96f4548b6005b98fb335adc093f28eb541696cf5fa7d3</citedby><cites>FETCH-LOGICAL-c5723-739c73a821cfe595b5da96f4548b6005b98fb335adc093f28eb541696cf5fa7d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1016%2Fj.febslet.2006.08.073$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0014579306010623$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,1411,1427,3537,27901,27902,45550,45551,46384,46808,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16979628$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Niwa, Kazuki</creatorcontrib><creatorcontrib>Nakamura, Mitsuhiro</creatorcontrib><creatorcontrib>Ohmiya, Yoshihiro</creatorcontrib><title>Stereoisomeric bio-inversion key to biosynthesis of firefly d-luciferin</title><title>FEBS letters</title><addtitle>FEBS Lett</addtitle><description>The chirality of the luciferin substrate is critical to the luciferin–luciferase reaction producing bioluminescence. In firefly, the biosynthetic pathway of
d-luciferin is still unclear, although it can be synthesized in vitro from
d-cysteine. Here, we show that the firefly produces both
d- and
l-luciferin, and that the amount of active
d-luciferin increases gradually with maturation stage. Studies of firefly body extracts indicate the possible conversion of
l-cysteine via
l-luciferin into
d-luciferin, suggesting that the biosynthesis is enzymatically regulated by stereoisomeric bio-inversion of
l-luciferin. We conclude that the selection of chirality in living organisms is not as rigid as previously thought.</description><subject>2-cyano-6-hydroxybenzothiazole</subject><subject>4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole</subject><subject>ABD-F</subject><subject>Animals</subject><subject>Bioluminescence</subject><subject>Biosynthesis</subject><subject>Bovine serum albumin</subject><subject>BSA</subject><subject>CHBT</subject><subject>CoA</subject><subject>coenzyme A</subject><subject>Enantiomer</subject><subject>Fireflies - chemistry</subject><subject>Fireflies - growth & development</subject><subject>Firefly</subject><subject>Firefly Luciferin - chemistry</subject><subject>Firefly Luciferin - metabolism</subject><subject>Luciferase</subject><subject>Luciferin</subject><subject>Stereoisomerism</subject><subject>TBP</subject><subject>tri-n-butylphosphine</subject><issn>0014-5793</issn><issn>1873-3468</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkUtP3DAUha2qCKaUnwDKil3CdRy_VggQj0pILKBrK3GuVQ-ZGOwMKP--jmakLunKsnXOudffIeSUQkWBiot15bBLA05VDSAqUBVI9o2sqJKsZI1Q38kKgDYll5odkR8prSHfFdWH5IgKLbWo1YrcP08YMfgUNhi9LTofSj9-YEw-jMUrzsUUlsc0j9MfTD4VwRXOR3TDXPTlsLXeZeP4kxy4dkh4sj-Pye-725ebh_Lx6f7XzdVjabmsWSmZtpK1qqbWIde8432rhWt4ozoBwDutXMcYb3sLmrlaYcebvK2wjrtW9uyYnO9y32J432KazMYni8PQjhi2yQiltKqBfSmkWlLBqchCvhPaGFLKHzNv0W_aOBsKZkFt1maP2iyoDSiTUWff2X7Atttg_8-1Z5sFDzvBpx9w_r9Uc3d7XT8vvS21gQAKol5mXe6iMKP98BhNsh5Hi31uwk6mD_6Lbf8C2duoKA</recordid><startdate>20061002</startdate><enddate>20061002</enddate><creator>Niwa, Kazuki</creator><creator>Nakamura, Mitsuhiro</creator><creator>Ohmiya, Yoshihiro</creator><general>Elsevier B.V</general><scope>6I.</scope><scope>AAFTH</scope><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>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope></search><sort><creationdate>20061002</creationdate><title>Stereoisomeric bio-inversion key to biosynthesis of firefly d-luciferin</title><author>Niwa, Kazuki ; Nakamura, Mitsuhiro ; Ohmiya, Yoshihiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5723-739c73a821cfe595b5da96f4548b6005b98fb335adc093f28eb541696cf5fa7d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>2-cyano-6-hydroxybenzothiazole</topic><topic>4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole</topic><topic>ABD-F</topic><topic>Animals</topic><topic>Bioluminescence</topic><topic>Biosynthesis</topic><topic>Bovine serum albumin</topic><topic>BSA</topic><topic>CHBT</topic><topic>CoA</topic><topic>coenzyme A</topic><topic>Enantiomer</topic><topic>Fireflies - chemistry</topic><topic>Fireflies - growth & development</topic><topic>Firefly</topic><topic>Firefly Luciferin - chemistry</topic><topic>Firefly Luciferin - metabolism</topic><topic>Luciferase</topic><topic>Luciferin</topic><topic>Stereoisomerism</topic><topic>TBP</topic><topic>tri-n-butylphosphine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Niwa, Kazuki</creatorcontrib><creatorcontrib>Nakamura, Mitsuhiro</creatorcontrib><creatorcontrib>Ohmiya, Yoshihiro</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>FEBS letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Niwa, Kazuki</au><au>Nakamura, Mitsuhiro</au><au>Ohmiya, Yoshihiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereoisomeric bio-inversion key to biosynthesis of firefly d-luciferin</atitle><jtitle>FEBS letters</jtitle><addtitle>FEBS Lett</addtitle><date>2006-10-02</date><risdate>2006</risdate><volume>580</volume><issue>22</issue><spage>5283</spage><epage>5287</epage><pages>5283-5287</pages><issn>0014-5793</issn><eissn>1873-3468</eissn><abstract>The chirality of the luciferin substrate is critical to the luciferin–luciferase reaction producing bioluminescence. In firefly, the biosynthetic pathway of
d-luciferin is still unclear, although it can be synthesized in vitro from
d-cysteine. Here, we show that the firefly produces both
d- and
l-luciferin, and that the amount of active
d-luciferin increases gradually with maturation stage. Studies of firefly body extracts indicate the possible conversion of
l-cysteine via
l-luciferin into
d-luciferin, suggesting that the biosynthesis is enzymatically regulated by stereoisomeric bio-inversion of
l-luciferin. We conclude that the selection of chirality in living organisms is not as rigid as previously thought.</abstract><cop>England</cop><pub>Elsevier B.V</pub><pmid>16979628</pmid><doi>10.1016/j.febslet.2006.08.073</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| issn | 0014-5793 1873-3468 |
| language | eng |
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| source | Wiley Free Content; MEDLINE; Wiley Online Library Journals Frontfile Complete; Elsevier ScienceDirect Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Alma/SFX Local Collection |
| subjects | 2-cyano-6-hydroxybenzothiazole 4-(aminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole ABD-F Animals Bioluminescence Biosynthesis Bovine serum albumin BSA CHBT CoA coenzyme A Enantiomer Fireflies - chemistry Fireflies - growth & development Firefly Firefly Luciferin - chemistry Firefly Luciferin - metabolism Luciferase Luciferin Stereoisomerism TBP tri-n-butylphosphine |
| title | Stereoisomeric bio-inversion key to biosynthesis of firefly d-luciferin |
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