Biocatalytic Desymmetrization Research Articles

Biocatalytic Desymmetrization of an Atropisomer with both an Enantioselective Oxidase and Ketoreductases

Alle Wege führen zu …︁ atropisomeren Diarylethern mit einer benzylischen Hydroxygruppe und einer Aldehydeinheit. Die Isomere wurden enantiomerenangereichert durch desymmetrisierende atropselektive enzymatische Oxidation (mit einer Galactose-Oxidase(GOase)-Variante) oder Reduktion (mit einer Ketoreduktase (KRED); siehe Schema) erhalten.

Biocatalytic Desymmetrization of an Atropisomer with both an Enantioselective Oxidase and Ketoreductases

All roads lead to …︁ atropisomeric diaryl ethers containing a benzylic hydroxy group and an aldehyde unit. The isomers were synthesized in enantiomerically enriched form by desymmetrizing atroposelective enzymatic oxidation (with a galactose oxidase (GOase) variant) or reduction (with a ketoreductase (KRED); see scheme).

Highly Stereoselective Synthesis of Substituted Prolyl Peptides Using a Combination of Biocatalytic Desymmetrization and Multicomponent Reactions

Ideal kombiniert: Optisch reine 3,4-disubstituierte 1-Pyrroline, die aus entsprechenden meso-Pyrrolidinen durch biokatalytische Desymmetrisierung mit Monoaminoxidase N (MAO-N) erhalten wurden, reagieren mit Carbonsäuren und Isocyaniden in einer Ugi-Mehrkomponentenreaktion hoch diastereoselektiv zu substituierten Prolylpeptiden mit großer Bedeutung in der Pharmazie. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Highly Stereoselective Synthesis of Substituted Prolyl Peptides Using a Combination of Biocatalytic Desymmetrization and Multicomponent Reactions

Time and pep-tide wait for no man: Optically pure 3,4-disubstituted 1-pyrrolines, generated from the corresponding meso-pyrrolidines by biocatalytic desymmetrization (MAO-N=monoamine oxidase N), react with carboxylic acids and isocyanides in a highly diastereoselective Ugi-type multicomponent reaction to give substituted prolyl peptides of high pharmaceutical relevance.

Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet–Spengler-type cyclization sequence

We have combined the biocatalytic desymmetrization of 3,4-cis-substituted meso-pyrrolidines with an Ugi-type multicomponent reaction followed in situ by a Pictet-Spengler-type cyclization reaction sequence for the rapid asymmetric synthesis of alkaloid-like polycyclic compounds.

A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions

A very short and efficient synthesis of the important drug candidate telaprevir, featuring a biocatalytic desymmetrization and two multicomponent reactions as the key steps, is presented. The classical issue of lack of stereoselectivity in Ugi- and Passerini-type reactions is circumvented. The atom economic and convergent nature of the synthetic strategy require only very limited use of protective groups.

Unprecedented biocatalytic desymmetrization of hexitols

An unprecedented biocatalytic desymmetrization of a dulcitol derivative leads to optically active hexitols. The best results have been obtained with PFL or Lipase PS, with ees superior to 98% and chemical yields of 75–86%. The absolute configurations of the title chiral compounds have been determined by transformation into known bromo derivatives, already utilized for the preparation of optically active tetrahydrofurans.

Enzyme-catalyzed desymmetrization of meso-skipped polyols to useful chiral building blocks

the biocatalytic desymmetrization, in presence of different enzymes, of two models of polyfunctionalized diols in a meso form was studied PFL was found to be the most selective enzyme with excellent results in chemical and optical yield with some of the tested substrates. The obtained chiral building block was utilized for some useful synthetic transformations toward the synthesis of natural products