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Cover Feature: Synthesis, Structure, and Cytotoxicity of Urukthapelstatin A Polyazole Cyclopeptide Analogs (Eur. J. Org. Chem. 27/2019)
Author(s) -
Oberheide Ansgar,
Schwenk Sebastian,
Ronco Cyril,
Semmrau Lisa Maria,
Görls Helmar,
Arndt HansDieter
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900954
Subject(s) - chemistry , natural product , ring (chemistry) , stereochemistry , azide , cover (algebra) , combinatorial chemistry , peptide , cytotoxicity , organic chemistry , mechanical engineering , biochemistry , engineering , in vitro
The Cover Feature illustrates the using of the aza ‐Wittig reaction for ring contraction of a peptide thiolactone, to provide intrinsically strained polyazole macrocycles. Like an experienced blacksmith actively forges rings, this transformation transfers the chemical energy of a localized azide into a reactive iminophosphorane for ring formation. Thereby a series of cytotoxic natural product analogs were synthesized from which a structure‐activity pattern for urukthapelstatin A was delineated. This work was supported by the Carl‐Zeiss‐Foundation. Picture credits: iStock/ CasarsaGuru. More information can be found in the Full Paper by H.‐D. Arndt et al.