Please use this identifier to cite or link to this item: doi:10.22028/D291-36312
Title: Stereoselective Syntheses of Deuterated Pipecolic Acids as Tools to Investigate the Stereoselectivity of the Hydroxylase GetF
Author(s): Neis, Nadine
Xie, Feng
Krug, Daniel
Zhao, Haowen
Siebert, Andreas
Binz, Tina M.
Fu, Chengzhang
Müller, Rolf
Kazmaier, Uli
Language: English
Title: European Journal of Organic Chemistry
Volume: 2022
Issue: 13
Publisher/Platform: Wiley
Year of Publication: 2022
Free key words: Biosynthesis
Claisen rearrangement
Synthetic methods
DDC notations: 500 Science
Publikation type: Journal Article
Abstract: Members of the GE81112 family are interesting candidates for the development of antibiotics. The configuration of the OH group on the pipecolic acid moiety plays a pivotal role in antibiotic activity. To investigate the stereoselectivity of the corresponding hydroxylase GetF, involved in the biosynthetic pathway, we synthesized the two deuterium-labeled pipecolic acid diastereomers in a highly stereoselective fashion via chelate-enolate Claisen rearrangement. The stereochemical outcome of the enzymatic hydroxylation step could easily be determined by analysis of mass differences between the products.
DOI of the first publication: 10.1002/ejoc.202200162
Link to this record: urn:nbn:de:bsz:291--ds-363126
ISSN: 1099-0690
Date of registration: 31-May-2022
Description of the related object: Supporting Information
Related object:
Faculty: NT - Naturwissenschaftlich- Technische Fakultät
Department: NT - Chemie
NT - Pharmazie
Professorship: NT - Prof. Dr. Uli Kazmaier
NT - Prof. Dr. Rolf Müller
Collections:SciDok - Der Wissenschaftsserver der Universität des Saarlandes

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