Document Detail


D-fructose-6-phosphate aldolase in organic synthesis: cascade chemical-enzymatic preparation of sugar-related polyhydroxylated compounds.
MedLine Citation:
PMID:  19222084     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Novel aldol addition reactions of dihydroxyacetone (DHA) and hydroxyacetone (HA) to a variety of aldehydes catalyzed by D-fructose-6-phosphate aldolase (FSA) are presented. In a chemical-enzymatic cascade reaction approach, 1-deoxynojirimycin and 1-deoxymannojirimycin were synthesized starting from (R)- and (S)-3-(N-Cbz-amino)-2-hydroxypropanal, respectively. Furthermore, 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4,5-trideoxy-1,4-imino-D-arabinitol were prepared from N-Cbz-glycinal. 1-Deoxy-D-xylulose was also synthesized by using HA as the donor and either 2-benzyloxyethanal or 2-hydroxyethanal as acceptors. In both cases the enzymatic aldol addition reaction was fully stereoselective, but with 2-hydroxyethanal 17 % of the epimeric product at C2, 1-deoxy-D-erythro-2-pentulose, was observed due to enolization/epimerization during the isolation steps. It was also observed that D-(-)-threose is a good acceptor substrate for FSA, opening new synthetic possibilities for the preparation of important novel complex carbohydrate-related compounds from aldoses. To illustrate this, 1-deoxy-D-ido-hept-2-ulose was obtained stereoselectively by the addition of HA to D-(-)-threose, catalyzed by FSA. It was found that the reaction performance depended strongly on the donor substrate, HA being the one that gave the best conversions to the aldol adduct. The examples presented in this work show the valuable synthetic potential of FSA for the construction of chiral complex polyhydroxylated sugar-type structures.
Authors:
Alda Lisa Concia; Carles Lozano; José A Castillo; Teodor Parella; Jesús Joglar; Pere Clapés
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  15     ISSN:  1521-3765     ISO Abbreviation:  Chemistry     Publication Date:  2009  
Date Detail:
Created Date:  2009-03-31     Completed Date:  2009-05-07     Revised Date:  2009-08-04    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  3808-16     Citation Subset:  IM    
Affiliation:
Biotransformation and Bioactive Molecules Group, Catalonia Institute for Advanced Chemistry-CSIC, Jordi Girona 18-26, 08034 Barcelona, Spain.
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MeSH Terms
Descriptor/Qualifier:
Biocatalysis
Fructose-Bisphosphate Aldolase / metabolism*
Fructosephosphates / chemistry*,  metabolism*
Hydroxylation
Magnetic Resonance Spectroscopy
Molecular Structure
Tetroses / chemistry,  metabolism
Chemical
Reg. No./Substance:
0/Fructosephosphates; 0/Tetroses; 1758-51-6/erythrose; 6814-87-5/fructose-6-phosphate; EC 4.1.2.13/Fructose-Bisphosphate Aldolase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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