THE REACTION-MECHANISM OF CHROMANOL-RING FORMATION CATALYZED BY TOCOPHEROL CYCLASE FROM ANABAENA-VARIABILIS KUTZING (CYANOBACTERIA)

Authors
STOCKER A NETSCHER T RUTTIMANN A MULLER RK SCHNEIDER H TODARO LJ DERUNGS G WOGGON WD
Citation
A. Stocker et al., THE REACTION-MECHANISM OF CHROMANOL-RING FORMATION CATALYZED BY TOCOPHEROL CYCLASE FROM ANABAENA-VARIABILIS KUTZING (CYANOBACTERIA), Helvetica Chimica Acta, 77(7), 1994, pp. 1721-1737
Citations number
24
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
77
Issue
7
Year of publication
1994
Pages
1721 - 1737
Database
ISI
SICI code
0018-019X(1994)77:7<1721:TROCFC>2.0.ZU;2-I
Abstract
Incubation of the synthetic O-18-labelled phytyl-hydraquinone (O-4-O-1 8)-2 with the tocopherol cyclase from Anabaena variabilis KUTZING (Cya nobacterin) in D2O furnished the doubly labelled gamma-tocopherol, (2R ,3S,4'R,8'R)-(1-O-18,3-H-2)-1. The chirality at C(3) was determined by two independent routes providing interlocking evidence that the enzym e-catalyzed ring closure proceeds by si-protonalion of the double bond of 2 and concomitant re-attack of the phenolic O-atom.