- Modular Total Synthesis of Farnesyl Analogues of Cell Wall Precursors Lipid i and II Containing the Staphylococcus aureus Pentaglycine Bridge Modification
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A scalable and modular total synthesis of 3-lipid I and 3-lipid II was accomplished by a novel route involving an efficient solid phase synthesis of the peptide fragment and an effective chemoenzymatic attachment of the second sugar moiety. The generality of this route was further documented by the synthesis of an analogue bearing the pentaglycine interpeptidic bridge modification characteristic for the human pathogen Staphylococcus aureus.
- Wingen, Lukas M.,Rausch, Marvin,Schneider, Tanja,Menche, Dirk
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supporting information
p. 10206 - 10215
(2020/09/03)
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- Assessment of structurally diverse philanthotoxin analogues for inhibitory activity on ionotropic glutamate receptor subtypes: Discovery of nanomolar, nonselective, and use-dependent antagonists
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An array of analogues of the wasp toxin philanthotoxin-433, in which the asymmetric polyamine moiety was exchanged for spermine and the headgroup replaced with a variety of structurally diverse moieties, was prepared using parallel solid-phase synthesis a
- Fr?lund, Sidsel,Bella, Angelo,Kristensen, Anders S.,Ziegler, Hanne L.,Witt, Matthias,Olsen, Christian A.,Str?mgaard, Kristian,Franzyk, Henrik,Jaroszewski, Jerzy W.
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experimental part
p. 7441 - 7451
(2011/02/24)
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- The kinetic characterization of Escherichia coli MurG using synthetic substrate analogues
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Bacterial resistance to existing antibiotics poses a serious threat to human health. Because the peptidoglycan surrounding bacterial cells is essential for survival, the enzymes involved in peptidoglycan biosynthesis are attractive targets for the design
- Ha, Sha,Chang, Emmanuel,Lo, Mei-Chu,Men, Hongbin,Park, Peter,Ge, Min,Walker, Suzanne
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p. 8415 - 8426
(2007/10/03)
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- Nε-carbonyl> Derivatives of Tri-L-lysine and Tetra-L-lysine as Potential Intermediates in the Block Polymer Synthesis of Macromolecular Drug Conjugates
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Tri-L-lysine and tetra-L-lysine derivatives were synthesized with Nε-carbonyl>(Nε-Teoc) protecting groups an all the lysines, or on all but the N-terminal lysine, and with Nα-(tert-butyloxycarbonyl) (Nα-Boc) or Nα-(9-fluorenylmethyloxycarbonyl) (Nα-Fmoc) groups on the N-terminal lysines.Treatment of the Boc/Teoc peptides with p-toluenesulfonic or 2,4,6-trimethylbenzenesulfonic acid led to Boc cleavage with Teoc retention only when the Teoc/Boc ratio was 1:1 or 2:1.In contrast, treatment of the Fmoc/Teoc peptides with liquid ammonia in a sealed vessel cleaved the Fmoc group without significant loss of Teoc groups even when the Fmoc/Teoc ratio was 3:1, showing that Fmoc and Teoc groups provide more selectivity than the Boc and Teoc combination.Nα-Fmoc and Nε-Teoc groups were both stable under catalytic hydrogenolysis conditions.This made it possible to prepare Nα-Fmoc-tri-L-lysine and Nα-Fmoc-tetra-L-lysine derivatives with Nε-Teoc groups on all but the N-terminal lysine and demonstrated that the triad Fmoc/Cbz/Teoc is superior to Boc/Cbz/Teoc in peptide synthesis involving the orthogonal protection strategy.
- Rosowsky, Andre,Wright, Joel E.
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p. 5551 - 5558
(2007/10/02)
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