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Regioselective Enzymatic Acylation of Aureolic Acids to Obtain Novel Analogues with Improved Antitumor Activity
Author(s) -
GonzálezSabín Javier,
Núñez Luz Elena,
Braña Alfredo F.,
Méndez Carmen,
Salas José A.,
Gotor Vicente,
Morís Francisco
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100944
Subject(s) - chemistry , acylation , regioselectivity , aglycone , lipase , moiety , enzyme , stereochemistry , substrate (aquarium) , organic chemistry , biochemistry , catalysis , glycoside , oceanography , geology
A variety of aureolic acids was efficiently obtained by lipase‐catalyzed regioselective acylation reactions of mithramycin and its analogues mithramycin SK and mithramycin SDK. The acylation took place in the aglycone moiety or in the B sugar unit, depending on the substrate, lipase and acyl donor considered. Most of the novel acylated derivatives showed antitumor activity at double digit nanomolar concentrations, in some cases significantly improving the activity of the parent drugs.