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Fayad, S. ; Jafari, A. ; Schuler, S.M.M.* ; Kurz, M.* ; Plettenburg, O. ; Hammann, P.E.* ; Bauer, A.* ; Jürjens, G. ; Pöverlein, C.*

Total synthesis of GE81112A: An orthoester-based approach.

J. Org. Chem. 88, 5597-5608 (2023)
Verlagsversion DOI PMC
Open Access Hybrid
Creative Commons Lizenzvertrag
The GE81112 series, consisting of three naturally occurring tetrapeptides and synthetic derivatives, is evaluated as a potential lead structure for the development of a new antibacterial drug. Although the first total synthesis of GE81112A reported by our group provided sufficient amounts of material for an initial in depth biological profiling of the compound, improvements of the routes toward the key building blocks were needed for further upscaling and structure-activity relationship studies. The major challenges identified were poor stereoselectivity in the synthesis of the C-terminal β-hydroxy histidine intermediate and a concise access to all four isomers of the 3-hydroxy pipecolic acid. Herein, we report a second-generation synthesis of GE81112A, which is also applicable to access further representatives of this series. Based on Lajoie's ortho-ester-protected serine aldehydes as key building blocks, the described route provides both a satisfactory improvement in stereoselectivity of the β-hydroxy histidine intermediate synthesis and a stereoselective approach toward both orthogonally protected cis and trans-3-hydroxy pipecolic acid.
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Publikationstyp Artikel: Journalartikel
Dokumenttyp Wissenschaftlicher Artikel
Schlagwörter Stereoselective-synthesis; Stereocontrolled Synthesis; Translation Initiation; Amino-acid; Derivatives; Efficient; Component; Inhibition; Equivalent; Congeners
Sprache englisch
Veröffentlichungsjahr 2023
HGF-Berichtsjahr 2023
ISSN (print) / ISBN 0022-3263
e-ISSN 1520-6904
Zeitschrift Journal of Organic Chemistry, The
Quellenangaben Band: 88, Heft: 9, Seiten: 5597-5608 Artikelnummer: , Supplement: ,
Verlag American Chemical Society (ACS)
Verlagsort 1155 16th St, Nw, Washington, Dc 20036 Usa
Begutachtungsstatus Peer reviewed
Institut(e) Institute of Medicinal Chemistry (IMC)
POF Topic(s) 30203 - Molecular Targets and Therapies
Forschungsfeld(er) Enabling and Novel Technologies
PSP-Element(e) G-506300-001
Förderungen Hessen State Ministry of Higher Education, Research and the Arts (HMWK)
DOI 10.1021/acs.joc.3c00094
WOS ID 000973168900001
Scopus ID 85152139491
PubMed ID 37023463
Erfassungsdatum 2023-10-06
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