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Volumn 118, Issue 42, 1996, Pages 10037-10040

Aristolochene synthase. Elucidation of the cryptic germacrene A synthase activity using the anomalous substrate dihydrofarnesyl diphosphate

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHETASE; TERPENOID;

EID: 0029948274     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961981b     Document Type: Article
Times cited : (54)

References (29)
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    • (b) Steroid biosynthesis: Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1991, 113, 4025-4026. Corey, E. J.; Virgil, S. C.; Liu, D. R.; Sarshar, S. J. Am. Chem. Soc. 1992, 114, 1524-1525. Corey, E. J.; Virgil, S. C.; Sarshar, S. J. Am. Chem. Soc. 1991, 113, 8171-8172. Corey, E. J.; Virgil, S. C.; Cheng, H. M.; Baker, C. H.; Matsuda, S. P. T.; Singh, V.; Sarshar, S. J. Am. Chem. Soc. 1995, 117, 11819-11820.
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    • note
    • For clarity, numbering in dihydrogermacrene A (6) has been based on numbering of the corresponding carbon atoms in the precursor dihy-drofarnesyl diphosphate (5).
  • 22
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    • note
    • In preliminary incubations, (7R)-6,7-dihydrofarnesyl diphosphate (5) was turned over by aristolochene synthase about twice as efficiently as was the corresponding (7S)-6,7-dihydrofarnesyl diphosphate. For this reason we decided to concentrate our efforts on the 7R enantiomer.
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    • unpublished
    • We cannot as yet rule out aberrant binding of dihydrofarnesyl diphosphate so as to generate dihydrogermacrene A with the 2-propenyl group in the unnatural configuration. Several derivatives of synthetic 6b have been prepared, but to date none have been suitable for X-ray crystallographic analysis (D. E. Cane and S. Tsubotani, unpublished).
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  • 27


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