Product profile of PEN3: The last unexamined oxidosqualene cyclase in arabidopsis thaliana

Organic Letters

Volumn 11, Issue 12, 2009, Pages 2627-2630

  Morlacchi, Pietro ^a   Wilson, William K ^a   Xiong, Quanbo ^a   Bhaduri, Aparna ^a   Sttivend, Diana ^a   Kolesnikova, Mariya D ^a   Matsuda, Seiichi P T ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABC TRANSPORTER; ARABIDOPSIS PROTEIN; LANOSTEROL SYNTHASE; MUTASE; PDR8 PROTEIN, ARABIDOPSIS; TRITERPENE;

ARABIDOPSIS; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENZYMOLOGY; HUMAN; METABOLISM; SYNTHESIS;

ARABIDOPSIS; ARABIDOPSIS PROTEINS; ATP-BINDING CASSETTE TRANSPORTERS; CYCLIZATION; HUMANS; INTRAMOLECULAR TRANSFERASES; MOLECULAR STRUCTURE; TRITERPENES;

EID: 67149126750     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9005745     Document Type: Article

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30. (c) In these papers, the pathway fork leading to 20R and 20S isomers (IIIb and IIIa) derives from different conformations of a 6-membered D-ring intermediate that incorporates a bridged C17-C20-C13 cation (chair form) or a C17-C20-C16 cation (boat form). The Supporting Information contains a side-by-side comparison of this mechanism with that of Figure 3.
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32. (b) Our preliminary NMR and GC-MS analyses of LUP5 products indicated a ∼2:2:1 of 2, 5, and 8, with minor products including 3, 4, and 6 (see the Supporting Information).
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35. Some cyclases containing F696 (F601 in squalene-hopene cyclase) make tetracyclic intermediates or products with a 17α side chain, e.g., tirucalla-7,24-dienol synthase in Ailanthus altissima (ref 9) and squalene-hopene cyclase (ref lc, Figure 20 and ref 16b, Figure 3).