ol502747t_si_001.pdf (3.79 MB)
Resorcylic Acid Lactone Biosynthesis Relies on a Stereotolerant Macrocyclizing Thioesterase
journal contribution
posted on 2014-11-21, 00:00 authored by Graham
W. Heberlig, Monica Wirz, Meng Wang, Christopher N. BoddyZearalenone
and radicicol are highly related resorcylic acid lactones
with the rare property of having opposite stereochemical configurations
of the secondary alcohol involved in lactone formation. The ability
of the thioesterases from the zearalenone and radicicol biosynthetic
pathways to macrocyclize both d and l configured
synthetic substrate analogs was biochemically characterized and showed
that both enzymes were highly stereotolerant, macrocyclizing both
substrates with similar kinetic parameters. This observed stereotolerance
is consistent with a proposed evolution of both natural products from
a common ancestral resorcylic acid lactone.