Document Detail

Transannular proton transfer in the cyclization of geranylgeranyl diphosphate to fusicoccadiene, a biosynthetic intermediate of fusicoccins.
MedLine Citation:
PMID:  19530695     Owner:  NLM     Status:  MEDLINE    
Enzymatic cyclization of geranylgeranyl diphosphate to fusicoccadiene involves a transannular proton transfer process. Label distribution in the cyclized products derived from deuterium-labeled GGDPs showed that a proton generated from C-10 migrates to C-6 in the intermediary dolabellane framework prior to the second ring formation. Although a direct 1,5-proton transfer would achieve this process, semiempirical MO calculations suggested an alternative pathway, which involves successive 1,4- and 1,5-proton transfers using C-2 as a springboard.
Tomonobu Toyomasu; Mai Tsukahara; Hiromichi Kenmoku; Masahide Anada; Hajime Nitta; Junko Ohkanda; Wataru Mitsuhashi; Takeshi Sassa; Nobuo Kato
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Organic letters     Volume:  11     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2009 Jul 
Date Detail:
Created Date:  2009-07-09     Completed Date:  2009-08-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3044-7     Citation Subset:  IM    
Department of Bioresource Engineering, Yamagata University, Tsuruoka, Yamagata 997-8555, Japan.
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MeSH Terms
Diterpenes / chemical synthesis*,  chemistry*
Models, Molecular*
Molecular Structure
Polyisoprenyl Phosphates
Reg. No./Substance:
0/Diterpenes; 0/Polyisoprenyl Phosphates; 0/dolabellane; 0/fusicoccadiene; 6699-20-3/geranylgeranyl pyrophosphate

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