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Cover Feature: A Versatile Boc Solid Phase Synthesis of Daptomycin and Analogues Using Site Specific, On‐Resin Ozonolysis to Install the Kynurenine Residue (Chem. Eur. J. 62/2019)
Author(s) -
Xu Buzhe,
Hermant Yann,
Yang SungHyun,
Harris Paul W. R.,
Brimble Margaret A.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904369
Subject(s) - daptomycin , ozonolysis , tryptophan , kynurenine , residue (chemistry) , peptide , chemistry , amino acid , combinatorial chemistry , stereochemistry , biochemistry , organic chemistry , biology , bacteria , vancomycin , genetics , staphylococcus aureus
Sub‐zero amino acid transformation : The cover demonstrates the low temperature conversion of the amino acid l ‐tryptophan to the unnatural l ‐Kynurenine (Kyn) under a beam of ozone. Kyn is essential to the bioactivity of the FDA‐approved, clinically‐used peptide antibiotic Daptomycin (Cubicin) but its unique molecular structure prevents its use in peptide synthesis. The canonical amino acid tryptophan is readily incorporated into the peptide sequence of Daptomycin; under ozonolysis rapid conversion into Kyn realises a novel chemical synthesis of the frontline antibiotic Daptomyin. More information can be found in the Full Paper by P. W. R. Harris, M. A. Brimble, et al. on page 14101.