2 research outputs found
Chemoenzymatic Synthesis and Inhibitory Activities of Hyacinthacines A1 and A2 Stereoisomers.
6 páginas,1 figura, 2 esquemas, 2 tablas.A novel straightforward chemoenzymatic
procedure for the synthesis of hyacinthacine stereoisomers
based on the aldol addition of dihydroxyacetone
phosphate (DHAP) to N-Cbz-prolinal under
catalysis by l-rhamnulose 1-phosphate aldolase
from E. coli is presented. The synthesis is complemented
by a simple and effective purification protocol
consisting of ion-exchange chromatography on
CM-sepharose. As examples, ( )-hyacinthacine A2
[the enantiomer of (+)-hyacinthacine A2], 7-deoxy-
2-epialexine (the enantiomer of 3-epihyacinthacine
A2), ent-7-deoxyalexine (the enantiomer of 7-deoxyalexine)
and 2-epihyacinthacine A2 were synthesized
by these procedures and characterized for the
first time. These new isomers were assayed as inhibitors
of glycosidases. As a result, ( )-hyacinthacine
A2 demonstrated to be a good inhibitor of a-d-glucosidase
from rice whereas the natural enantiomer,
hyacinthacine A2, was not. Moreover, a new family
of inhibitors of a-l-rhamnosidase was uncovered.Financial support from the Spanish MEC (CTQ2005–25182-
E, CTQ2006–01080 and CTQ2006–01345/BQU), La Marat5
de TV3 foundation (Ref: 050931) and Generalitat de Catalunya
DURSI 2005-SGR-00698 is acknowledged. J. Calveras
acknowledges the CSIC UAs pre-doctoral scholarship programs.Peer reviewe