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Jürjens, G. ; Schuler, S.M.M.* ; Kurz, M.* ; Petit, S.* ; Couturier, C.* ; Jeannot, F.* ; Nguyen, F.* ; Wende, R.C.* ; Hammann, P.E.* ; Wilson, D.N.* ; Bacqué, E.* ; Pöverlein, C.* ; Bauer, A.*

Total synthesis and structural revision of the antibiotic tetrapeptide GE81112A.

Angew. Chem.-Int. Edit. 57, 12157-12161 (2018)
Postprint DOI PMC
Open Access Green
The total synthesis of the naturally occurring antibiotic GE81112A, a densely functionalized tetrapeptide, is reported. Comparison of spectral data with those of the natural product and the lack of biological activity of the synthesized compound led us to revise the published configuration of the 3-hydroxypipecolic acid moiety. This hypothesis was fully validated by the synthesis of the corresponding epimer.
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Publication type Article: Journal article
Document type Scientific Article
Keywords Antibiotics ; Non-ribosomal Peptide Synthesis ; Peptides ; Structural Revision ; Total Synthesis; Natural-products; Initiation Complex; Translation; Acid; Inhibition; Equivalent
Language
Publication Year 2018
HGF-reported in Year 2018
ISSN (print) / ISBN 1433-7851
e-ISSN 1521-3773
Quellenangaben Volume: 57, Issue: 37, Pages: 12157-12161 Article Number: , Supplement: ,
Publisher Wiley
Publishing Place Weinheim
Reviewing status Peer reviewed
Institute(s) Institute of Medicinal Chemistry (IMC)
POF-Topic(s) 30203 - Molecular Targets and Therapies
Research field(s) Enabling and Novel Technologies
PSP Element(s) G-506300-001
PubMed ID 30004165
Erfassungsdatum 2018-07-16