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Saxitoxin
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==Structure and synthesis== Saxitoxin [[dihydrochloride]] is an [[Amorphous solid|amorphous]] [[Hygroscopy|hygroscopic]] solid, but [[X-ray crystallography]] of crystalline derivatives enabled the structure of saxitoxin to be determined.<ref>{{cite journal |author1=Bordner J. |author2=Thiessen W. E. |author3=Bates H. A. |author4=Rapoport H. | year = 1975 | title = The structure of a crystalline derivative of saxitoxin. The structure of saxitoxin | journal = Journal of the American Chemical Society | volume = 97 | issue = 21| pages = 6008β12 | doi=10.1021/ja00854a009|pmid=1176726 |bibcode=1975JAChS..97.6008B }}</ref><ref>{{cite journal |author1=Schantz E. J. |author2=Ghazarossian V. E. |author3=Schnoes H. K. |author4=Strong F. M. |author5=Springer J. P. |author6=Pezzanite J. O. |author7=Clardy J. | year = 1975 | title = The structure of saxitoxin | journal = Journal of the American Chemical Society | volume = 97 | issue = 5| pages = 1238β1239 | doi=10.1021/ja00838a045|pmid=1133383 |bibcode=1975JAChS..97.1238S }}</ref> [[Oxidation]] of saxitoxin generates a highly [[Fluorescence|fluorescent]] [[purine]] derivative which has been utilized to detect its presence.<ref>{{cite journal |author1=Bates H. A. |author2=Kostriken R. |author3=Rapoport H. | year = 1978 | title = A chemical assay for saxitoxin. Improvements and modifications | journal = Journal of Agricultural and Food Chemistry | volume = 26 | issue = 1| pages = 252β4 | doi=10.1021/jf60215a060|pmid=621331 |bibcode=1978JAFC...26..252B }}</ref> Several [[Total synthesis|total syntheses]] of saxitoxin have been accomplished.<ref>{{cite journal |author1=Tanino H. |author2=Nakata T. |author3=Kaneko T. |author4=Kishi Y. | year = 1997 | title = A stereospecific total synthesis of d,l-saxitoxin | doi = 10.1021/ja00450a079 |pmid=850038 | journal = Journal of the American Chemical Society | volume = 99 | issue = 8| pages = 2818β9 |bibcode=1977JAChS..99.2818T }}</ref><ref>{{cite journal |author1=Bhonde V. R. |author2=Looper R. E. | year = 2011 | title = A stereocontrolled synthesis of (+)-saxitoxin | journal = Journal of the American Chemical Society | volume = 133 | issue = 50| pages = 20172β4 | doi=10.1021/ja2098063|pmid=22098556 |pmc=3320040|bibcode=2011JAChS.13320172B }}</ref><ref>{{cite journal |author1=Fleming J. J. |author2=McReynolds M. D. |author3=Du Bois J. | year = 2007 | title = (+)-Saxitoxin: a first and second generation stereoselective synthesis | journal = Journal of the American Chemical Society | volume = 129 | issue = 32| pages = 9964β75 | doi=10.1021/ja071501o | pmid=17658800|bibcode=2007JAChS.129.9964F }}</ref>
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