From amino alcohol to aminopolyol: one-pot multienzyme oxidation and aldol addition

Applied Microbiology and Biotechnology
Milja PešićGregorio Alvaro

Abstract

In this work, the successful coupling of enzymatic oxidation and aldol addition reactions for the synthesis of a Cbz-aminopolyol from a Cbz-amino alcohol was achieved for the first time in a multienzymatic one-pot system. The two-step cascade reaction consisted of the oxidation of Cbz-ethanolamine to Cbz-glycinal catalyzed by chloroperoxidase from the fungus Caldariomyces fumago and aldol addition of dihydroxyacetone phosphate to Cbz-glycinal catalyzed by rhamnulose-1-phosphate aldolase expressed as a recombinant enzyme in Escherichia coli, yielding (3R,4S)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1-O-phosphonopent-2-ulose. Tools of enzymatic immobilization, reactor configurations, and modification of the reaction medium were applied to highly increase the production of the target compound. While the use of soluble enzymes yielded only 23.6 % of Cbz-aminopolyol due to rapid enzyme inactivation, the use of immobilized ones permitted an almost complete consumption of Cbz-ethanolamine, reaching Cbz-aminopolyol yields of 69.1 and 71.9 % in the stirred-tank and packed-bed reactor, respectively. Furthermore, the reaction production was 18-fold improved when it was catalyzed by immobilized enzymes in the presence of 5 % (v/v) dioxane, r...Continue Reading

References

Aug 12, 1983·Biochemical and Biophysical Research Communications·J GeigertJ Wadsworth
Jul 15, 1982·Analytical Biochemistry·L Andersson, R Wolfenden
Apr 17, 1999·Trends in Biotechnology·S ColonnaP Pasta
Oct 14, 2000·The Journal of Organic Chemistry·R SchoevaartR A Sheldon
May 31, 1996·The Journal of Organic Chemistry·Frederick J. Lakner, Lowell P. Hager
Nov 23, 2005·Biotechnology and Bioengineering·Trinitat SuauJosep López-Santín
Nov 1, 1990·Applied and Environmental Microbiology·T A Kadima, M A Pickard
Apr 15, 2006·Applied Microbiology and Biotechnology·Anne K Samland, Georg A Sprenger
May 22, 2007·BMC Biotechnology·Jian-Zhong Liu, Min Wang
May 16, 2008·Journal of Biotechnology·Carl Elovson GreyPatrick Adlercreutz
May 1, 2009·Biotechnology Letters·Li-Hua ZhangQuan-Guo Zhai
Dec 29, 2009·Current Opinion in Chemical Biology·Fernando Lopez-Gallego, Claudia Schmidt-Dannert
Jan 7, 2010·Chemistry, an Asian Journal·Jian Zhou
Jan 15, 2010·Current Opinion in Chemical Biology·Pere ClapésAnne K Samland
Apr 14, 2010·International Journal of Molecular Sciences·Dirk JungMartin Hartmann
Sep 14, 2010·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Marcela AyalaRafael Vazquez-Duhalt

Citations

Feb 11, 2021·Applied Microbiology and Biotechnology·Yi JiangTengfei Wang

Related Concepts

Rhamnulose-1-phosphate aldolase
Polyol
3-hydroxybutanal
Aldehyde-Lyases
Aldehydes
Amino Alcohols
Cochliobolus
Biotechnology
Chloride Peroxidase
Alkalescens-Dispar Group

Related Feeds

Bioinformatics in Biomedicine

Bioinformatics in biomedicine incorporates computer science, biology, chemistry, medicine, mathematics and statistics. Discover the latest research on bioinformatics in biomedicine here.