Enzyme-triggered opening of an epoxide: Chemoenzymatic synthesis of (2R,5R)- and (2S,5R)-pityol

Mischitz, Martin; Hackinger, Alexandra; Francesconi, Iris; Faber, Kurt

doi:10.1016/s0040-4020(01)85340-0

Cited by 11 publications

(2 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The latter spontaneously opened the epoxide in an S N 2 fashion to furnish diastereomeric tetrahydrofuran derivatives 30a and 30b, which could be separated by conventional column chromatography. 23 Both compounds are bioactive constituents of bark beetle pheromones.…”

Section: Domino Reactions Initiated By An Enzymatically Liberated Nuc...mentioning

confidence: 99%

Untitled

2001

Self Cite

View full text Add to dashboard Cite

Section: Domino Reactions Initiated By An Enzymatically Liberated Nuc...mentioning

confidence: 99%

Untitled

2001

Self Cite

View full text Add to dashboard Cite

“…This reaction was investigated in detail and the formation of the final ring product could be explained by the enzyme-catalyzed formation of a reactive (anionic) intermediate by enzymatic hydrolysis of the ester moiety, which spontaneously underwent a ring closure reaction through intramolecular nucleophilic substitution at the oxirane group (i.e., ring opening). This reaction, for which there are only few precedents in the literature, did not require an epoxide hydrolase activity 148 and aroused great interest in Kurt's group for enzymatically triggered domino reactions for asymmetric synthesis. 40,41,43,47,48,149 Searching "Nitro to Amine", Finding "Nitro to Aldehyde", the Bio-Nef Reaction.…”

Section: ■ Introductionmentioning

confidence: 99%

A Career in Biocatalysis: Kurt Faber

2022

View full text Add to dashboard Cite

a synthetic organic chemist by training, strongly influenced the field of biocatalysis throughout the course of his four-decade career (from the late 1980s to the early 2020s). The evolution of his career has gone hand in hand with the development of biocatalysis into a mature and versatile discipline originally deep-rooted in organic chemistry that quickly integrated techniques from molecular biology. His work has provided numerous grounds for recognizing natural catalysts as essential tools in organic synthesis, complementing the more chemical approaches. An important aspect of Kurt Faber's career encompasses teaching, mentoring, and encouraging the development of younger scientists worldwide. His book, Biotransformations in Organic Chemistry, now in its seventh edition, has become a recognized tool for training generations of chemists and biotechnologists and remains a reference worldwide. At Biotrans 2021, the 15th International Symposium on Biocatalysis and Biotransformations (originally scheduled to be held in Graz, Austria, and eventually held online due to the COVID-19 pandemic), Kurt Faber received the Biotrans senior award in recognition of his innovative contributions to the field. In this Account, we would like to acknowledge his contributions to the field of biocatalysis, highlighting both the growing importance of this discipline in many (industrial) sectors and the profound changes that have occurred in recent decades, while reflecting on some of Kurt Faber's most important discoveries and his legacy to this field.

show abstract