88223-99-8Relevant academic research and scientific papers
Simplified Novel Muraymycin Analogues; using a Serine Template Strategy for Linking Key Pharmacophores
Patel, Bhautikkumar,Kerr, Rachel V,Malde, Alpeshkumar K,Zunk, Matthew,Bugg, Timothy D. H.,Grant, Gary,Rudrawar, Santosh
supporting information, p. 1429 - 1438 (2020/06/17)
The present status of antibiotic research requires the urgent invention of novel agents that act on multidrug-resistant bacteria. The World Health Organization has classified antibiotic-resistant bacteria into critical, high and medium priority according to the urgency of need for new antibiotics. Naturally occurring uridine-derived “nucleoside antibiotics” have shown promising activity against numerous priority resistant organisms by inhibiting the transmembrane protein MraY (translocase I), which is yet to be explored in a clinical context. The catalytic activity of MraY is an essential process for bacterial cell viability and growth including that of priority organisms. Muraymycins are one subclass of naturally occurring MraY inhibitors. Despite having potent antibiotic properties, the structural complexity of muraymycins advocates for simplified analogues as potential lead structures. Herein, we report a systematic structure-activity relationship (SAR) study of serine template-linked, simplified muraymycin-type analogues. This preliminary SAR lead study of serine template analogues successfully revealed that the complex structure of naturally occurring muraymycins could be easily simplified to afford bioactive scaffolds against resistant priority organisms. This study will pave the way for the development of novel antibacterial lead compounds based on a simplified serine template.
Solid-phase synthesis of peptide selenoesters: Via a side-chain anchoring strategy
Hanna, Cameron C.,Kulkarni, Sameer S.,Watson, Emma E.,Premdjee, Bhavesh,Payne, Richard J.
, p. 5424 - 5427 (2017/07/06)
Peptide selenoesters have recently emerged as key building blocks for the ligation-based assembly of large polypeptides and proteins. Herein, we report an efficient solid-phase method for the high yielding and epimerisation-free synthesis of peptide selenoesters using a side-chain immobilisation strategy.
Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis
Lang, Simon B.,O'Nele, Kathryn M.,Tunge, Jon A.
, p. 13606 - 13609 (2015/02/02)
A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant amino and phenylacetic allyl esters. This operationally simple process produces CO2as the only b
Solid-phase synthesis of piperazinones via disrupted ugi condensation
Treder, Adam P.,Tremblay, Marie-Claude,Yudin, Andrei K.,Marsault, Eric
, p. 4674 - 4677 (2015/03/30)
The first application of aziridine aldehyde dimers in solid-phase synthesis is reported. The solid-supported disrupted Ugi condensation between an aziridine aldehyde dimer, isonitrile, and backbone-anchored amino acids delivered N-acyl aziridine intermediates, which were reacted with nucleophiles to yield the corresponding piperazinones. Subsequent cleavage from the resin provided a diverse set of 2,3,6-trisubstituted piperazinones starting from various amino acids, aziridine aldehydes, and nucleophiles.
Synthetic studies of micropeptin T-20, a novel 3-amino-6-hydroxy-2-piperidone (Ahp)-containing cyclic depsipeptide
Yokokawa, Fumiaki,Inaizumi, Akiko,Shioiri, Takayuki
, p. 5903 - 5908 (2007/10/03)
The synthetic studies of micropeptin T-20 including the late installation of the Ahp (3-amino-6-hydroxy-2-piperidone) residue through oxidation and cyclization of a homoserine to the requisite hemiaminal are described.
The (2-phenyl-2-trimethylsilyl)ethoxycarbonyl (Psoc) group - A novel amino protecting group
Wagner,Heiner,Kunz
, p. 1753 - 1756 (2007/10/03)
A novel silicon containing protecting group has been developed based on the known 2-(trimethylsilyl)ethyl system. The new protecting group is cleaved under very mild conditions by treatment with tetra-n-butylammonium fluoride in CH2Cl2 much more rapidly than the 2-(trimethylsilyl)ethoxycarbonyl group, leading to less side reactions.
