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Influence of N-amino protecting group on aldolase-catalyzed aldol additions of dihydroxyacetone phosphate to amino aldehydes

AuthorsCalveras Ibáñez, Jordi; Bujons Vilàs, Jordi ; Parella, Teodor; Crehuet, Ramón ; Espelt, Laia; Joglar Tamargo, Jesús ; Clapés Saborit, Pere
KeywordsN-protecting groups
Dihydroxyacetone phosphate (DHAP)
Aldolase-catalyzed aldol
Amino aldehydes
Unexpected reactions
Issue Date9-Jan-2006
CitationTetrahedron 62(11): 2648-2656 (2006)
AbstractThis work examines the influence of N-protecting groups on the conversion and stereoselectivity of dihydroxyacetone phosphate (DHAP) dependent aldolase-catalyzed aldol additions of DHAP to N-protected-3-aminopropanal. Phenylacetyl-(PhAc-), tert-butyloxycarbonyl- (tBoc-) and fluoren-9-ylmethoxycarbonyl- (Fmoc-)-3-aminopropanal were evaluated as substrates for d-fructose 1,6-bisphosphate aldolase from rabbit muscle (RAMA), and l-rhamnulose-1-phosphate aldolase (RhuA) and l-fuculose-1-phosphate aldolase (FucA), both from Escherichia coli. Using PhAc and tBoc ca. 70% conversions to the aldol adduct were achieved, whereas Fmoc gave maximum conversions of ca. 25%. The stereoselectivity of the DHAP-aldolases did not depend on the N-protected-3-aminopropanal derivative. Moreover, inversion of FucA stereoselectivity relative to that obtained with the natural l-lactaldehyde was observed. Both N-PhAc and tBoc adduct product derivatives were successfully deprotected by penicillin G acylase (PGA)-catalyzed hydrolysis at pH 7 and by treatment with aqueous TFA (6% v/v), respectively. However, the corresponding cyclic imine sugars could not be isolated, presumable due to the presence of a highly reactive primary amine and a keto group in the molecule, which lead to a number of unexpected reactions.
Description9 pages, 3 scheme, 1 figure, 1 table.-- Printed version published Mar 13, 2006.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2005.12.031
Appears in Collections:(IQAC) Artículos
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