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Occurrence of Cationic Intermediates and Deficient Control during the Enzymatic Cyclization of Squalene to Hopanoids
Author(s) -
PaleGrosdemange Catherine,
Feil Corinna,
Rohmer Michel,
Poralla Karl
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980904)37:16<2237::aid-anie2237>3.0.co;2-9
Subject(s) - squalene , cyclase , chemistry , stereochemistry , enzyme , substrate (aquarium) , hopanoids , terpene , biosynthesis , cationic polymerization , squalene monooxygenase , biochemistry , organic chemistry , biology , ecology , paleontology , structural basin , source rock
Tetracyclic triterpenes (for example, 3 ) are formed as minor products of the cyclization of squalene ( 1 ) by squalene/hopene cyclase; they have also been found in vivo. The identification of these side products offers new insight into the complex biosynthesis of the hopane skeleton, and proves that the enzyme has no absolute control of the conformation of the acyclic substrate squalene and that tetra‐ and pentacyclic carbocationic intermediates are involved (for example, 2 ) in the cyclization process.