Stereochemical investigations of the Tetrahymena cyclase, a model system for euphane/tirucallane biosynthesis.
Org Biomol Chem
; 15(13): 2823-2830, 2017 Mar 28.
Article
em En
| MEDLINE
| ID: mdl-28287229
ABSTRACT
The squalene cyclase of Tetrahymena pyriformis cyclizes 2,3-dihydrosqualene to euph-7-ene. This was used as a model for euphane biosynthesis. D-ring formation was demonstrated to involve pre-chair folding through an experiment with 2,3-dihydro-5-oxasqualene. This requires that a non-least motion rotation (120°) of the C17-20 bond in the intermediate deoxydammaranyl cation occurs before the first 1,2-hydride shift. Truncated substrates relieved the hindrance associated with this rotation and permitted a least motion pathway. Several triterpenes were found to be minor products of the Tetrahymena cyclase.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Esqualeno
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Tetrahymena pyriformis
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Triterpenos
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Liases
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Modelos Biológicos
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article