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  • Concerted nature of AB ring formation in the enzymatic cyclization of squalene to hopenes.

Concerted nature of AB ring formation in the enzymatic cyclization of squalene to hopenes.

Organic letters (2004-05-21)
B Andes Hess, Lidia Smentek
ABSTRACT

The cyclization of the A-B rings of squalene to hopene is studied computationally (DFT). A transition structure is found for a concerted, asynchronous pathway for the formation of chair-chair decalin carbocation. The computationally derived conformer leading to this asynchronous transition structure is remarkably similar to the analogous region of 2-azasqualene encapsulated by squalene-hopene cyclase recently reported by Schulz. A concerted A-B ring closure is likely to occur in the cyclization of squalene to hopene. [structure--see text]

MATERIALS
Product Number
Brand
Product Description

Supelco
Hop-22(29)-ene solution, 0.1 mg/mL in isooctane, analytical standard