131614-83-0Relevant academic research and scientific papers
Antibacterial activity of xylose-derived LpxC inhibitors – Synthesis, biological evaluation and molecular docking studies
Dreger, Alexander,Hoff, Katharina,Agoglitta, Oriana,Hotop, Sven-Kevin,Br?nstrup, Mark,Heisig, Peter,Kirchmair, Johannes,Holl, Ralph
, (2021)
LpxC inhibitors represent a promising class of novel antibiotics selectively combating Gram-negative bacteria. In chiral pool syntheses starting from D- and L-xylose, a series of four 2r,3c,4t-configured C-furanosidic LpxC inhibitors was obtained. The synthesized hydroxamic acids were tested for antibacterial and LpxC inhibitory activity, the acquired biological data were compared with those of previously synthesized C-furanosides, and molecular docking studies were performed to rationalize the observed structure-activity relationships. Additionally, bacterial uptake and susceptibility to efflux pump systems were investigated for the most promising stereoisomers.
Synthesis and absolute configuration assignment of albucidin: A late-stage reductive deiodination by visible light photocatalysis
Zhang, Hu,Liu, Peng-Fei,Chen, Qiong,Wu, Qiong-You,Seville, Anne,Gu, Yu-Cheng,Clough, John,Zhou, Shao-Lin,Yang, Guang-Fu
, p. 3482 - 3485 (2016/04/09)
The synthesis of albucidin and its enantiomer are described. It involves a visible-light photocatalysis deiodination at the late stage. The absolute configuration of natural albucidin is determined as (1R,3S). This work provides a basis for structural mod
Oxetane cis- and trans β-amino-acid scaffolds from d-xylose by efficient SN2 reactions in oxetane rings: Methyl and hydroxymethyl analogues of the antibiotic oxetin, an oxetane β-amino-acid
Jenkinson, Sarah F.,Harris, Timothy,Fleet, George W.J.
, p. 2667 - 2679 (2007/10/03)
Highly regioselective reactions of a benzylidene-protected oxetane with (i) triethylsilane-trifluoroacetic acid and (ii) Hanessian-Hullar bromination provide efficient access to 3-hydroxyoxetane carboxylates in which only the C-3 OH is unprotected. Subseq
cis- and trans-3-Azido-oxetane-2-carboxylate scaffolds: Hexamers of oxetane cis-β-amino acids
Barker, Sarah F.,Angus, Donald,Taillefumier, Claude,Probert, Michael R.,Watkin, David J.,Watterson, Mark P.,Claridge, Timothy D.W.,Hungerford, Natasha L.,Fleet, George W.J.
, p. 4247 - 4250 (2007/10/03)
Efficient synthesis of both cis- and trans-3-azido-oxetane-2-carboxylates relies upon efficient nucleophilic displacements of 3-O-triflates of oxetanes by trifluoroacetate and azide. Such structures are scaffolds for incorporation of oxetane-β-amino acids into oligomers; the synthesis of a series of protected β-hexapeptides and the X-ray crystal structure of methyl 2,4-anhydro-6-deoxy-5-O-benzyl-L-altronate are reported.
Spectroscopic, crystallographic and computational studies of the formation and isomerization of cyclic acetals and ketals of pentonolactones
Han,Joullie,Fokin,Petasis
, p. 2535 - 2562 (2007/10/02)
The different reactivities of D-ribonolactone, L-arabinonolactone, D-xylonolactone, D-lyxonolactone and 2-deoxy-D-ribonolactone toward benzaldehyde and acetone in acidic media, were examined. The reactions involved complex equilibria and were investigated with extensive 13C NMR studies as well as X-ray crystallographic analysis of selected products. Molecular mechanics (MM2) and semiempirical (PM3 and AM1) calculations of some derivatives were carried out in order to facilitate structural and conformational assignments. The differences in reactivity observed for the reactions of D-pentono-1,4-lactones with benzaldehyde and acetone are rationalized in terms of their structural and conformational features.
Use of D-Ribonolactone in Organic Synthesis. 2. Scope and Utility
Chen, Shin-Yih,Joullie, Madeleine M.
, p. 2168 - 2174 (2007/10/02)
The scope and utility of D-ribonolactone (1) as chiral template for the synthesis of optically active γ-lactones which are important precursors for many natural products are discussed.The regio- and stereoselective functionalization of 1 is examined.
