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L-Rhamnulose-1-phosphate and L-fuculose-1-phosphate aldolase mediated multi-enzyme cascade systems for nitrocyclitol synthesis

AuthorsCamps Bres, Flora; Guérard-Hélaine, Christine; Hélaine, Virgil; Fernandes, Carlos; Sánchez-Moreno, Israel ; Traïkia, Mounir; García-Junceda, Eduardo ; Lemaire, Marielle
Henry reaction
Cascade process
Issue Date2015
CitationJournal of Molecular Catalysis B: Enzymatic 114 : 50–57 (2015)
AbstractOne-pot multistep stereoselective cascade reactions were implemented for the straightforward synthe-sis of various nitrocyclitols. Two kinases, an aldolase and a phosphatase were involved in this process,together with a spontaneous intramolecular Henry reaction to provide the nitrocyclitol moiety. The C Cbond formation catalysed by the aldolase and the nitroaldol reactions were key steps to build the carbocy-cle stereoselectively. The aldolase acceptor substrates were all 4-nitrobutanal structurally based, eitherhydroxylated or unsubstituted at the C2 and/or C3 positions. l-Fuculose-1-phosphate aldolase (FucA)catalysed the formation of the expected (R,R)- or d-erythro aldol, except in the case of 4-nitrobutanal,from which the epimeric (R,S)- or l-threo aldol was also formed. l-Rhamnulose-1-phosphate aldolase con-sistently formed the expected (R,S)- or l-threo aldol together with a minor amount of (R,R)- or d-erythroaldol. The intramolecular Henry reaction was also found to be stereoselective, occurring spontaneouslyonce the aldol was formed due to the presence of both ketone and a terminally positioned nitro group.The combination of this set of reactions successfully furnished 11 nitrocyclitols which have not beendescribed previously in the literature.
Publisher version (URL)http://dx.doi.org/10.1016/j.molcatb.2014.10.016
Appears in Collections:(IQOG) Artículos
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