20409-32-9Relevant academic research and scientific papers
Mechanistic Investigation of 1,2-Diol Dehydration of Paromamine Catalyzed by the Radical S-Adenosyl- l -methionine Enzyme AprD4
Yeh, Yu-Cheng,Kim, Hak Joong,Liu, Hung-Wen
supporting information, p. 5038 - 5043 (2021/05/04)
AprD4 is a radical S-adenosyl-l-methionine (SAM) enzyme catalyzing C3′-deoxygenation of paromamine to form 4′-oxo-lividamine. It is the only 1,2-diol dehydratase in the radical SAM enzyme superfamily that has been identified and characterized in vitro. The AprD4 catalyzed 1,2-diol dehydration is a key step in the biosynthesis of several C3′-deoxy-aminoglycosides. While the regiochemistry of the hydrogen atom abstraction catalyzed by AprD4 has been established, the mechanism of the subsequent chemical transformation remains not fully understood. To investigate the mechanism, several substrate analogues were synthesized and their fates upon incubation with AprD4 were analyzed. The results support a mechanism involving formation of a ketyl radical intermediate followed by direct elimination of the C3′-hydroxyl group rather than that of a gem-diol intermediate generated via 1,2-migration of the C3′-hydroxyl group to C4′. The stereochemistry of hydrogen atom incorporation after radical-mediated dehydration was also established.
MODULAR SYNTHESIS OF AMINOGLYCOSIDES
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Paragraph 0579, (2019/10/29)
The present disclosure relates to novel methods for preparing antibacterial aminoglycoside compounds and the compounds used in such preparations.
AMINOGLYCOSIDES AND USES THEREOF
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, (2019/03/17)
Provided herein are aminoglycoside compounds, such as compounds of formula (I), (II), (III), (IV), (IVa), (V), (VI), (VIIa), or (VIIb) or pharmaceutically acceptable salts, solvates, stereoisomers, or tautomers of any of the foregoing, useful as therapeutic or prophylactic agents. Also provided herein are methods for their preparation. The compounds may be useful in treating a bacterial infection in a subject, for example a Gram-negative bacterial infection.
Synthesis of 1,5-Anhydro-D-fructose derivatives and evaluation of their inflammasome inhibitors
Goto, Kohtaro,Ideo, Hiroko,Tsuchida, Akiko,Hirose, Yuriko,Maruyama, Ikuro,Noma, Satoshi,Shirai, Takashi,Amano, Junko,Mizuno, Mamoru,Matsuda, Akio
supporting information, p. 3763 - 3772 (2018/07/13)
Synthesis of several 1,5-Anhydro-D-fructose (1,5-AF) derivatives to evaluate inhibitory activities of the inflammasome was carried out. Recently, 1,5-AF reported to suppress the inflammasome, although with only low activity. We focused on the hydration of
3-Fluoroazetidinecarboxylic Acids and trans,trans- 3,4-Difluoroproline as Peptide Scaffolds: Inhibition of Pancreatic Cancer Cell Growth by a Fluoroazetidine Iminosugar
Liu, Zilei,Jenkinson, Sarah F.,Vermaas, Tom,Adachi, Isao,Wormald, Mark R.,Hata, Yukako,Kurashima, Yukiko,Kaji, Akira,Yu, Chu-Yi,Kato, Atsushi,Fleet, George W. J.
, p. 4244 - 4258 (2015/05/13)
Reverse aldol opening renders amides of 3-hydroxyazetidinecarboxylic acids (3-OH-Aze) unstable above pH 8. Aze, found in sugar beet, is mis-incorporated for proline in peptides in humans and is associated with multiple sclerosis and teratogenesis. Aze-con
DETECTION OF MYCOBACTERIA
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Page/Page column 47, (2011/04/18)
A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.
Synthesis, improved antisense activity and structural rationale for the divergent RNA affinities of 3′-fluoro hexitol nucleic acid (FHNA and Ara-FHNA) modified oligonucleotides
Egli, Martin,Pallan, Pradeep S.,Allerson, Charles R.,Prakash, Thazha P.,Berdeja, Andres,Yu, Jinghua,Lee, Sam,Watt, Andrew,Gaus, Hans,Bhat, Balkrishen,Swayze, Eric E.,Seth, Punit P.
supporting information; experimental part, p. 16642 - 16649 (2011/12/13)
The synthesis, biophysical, structural, and biological properties of both isomers of 3′-fluoro hexitol nucleic acid (FHNA and Ara-FHNA) modified oligonucleotides are reported. Synthesis of the FHNA and Ara-FHNA thymine phosphoramidites was efficiently acc
Molecular recognition in the P2Y14 receptor: Probing the structurally permissive terminal sugar moiety of uridine-5′-diphosphoglucose
Ko, Hyojin,Das, Arijit,Carter, Rhonda L.,Fricks, Ingrid P.,Zhou, Yixing,Ivanov, Andrei A.,Melman, Artem,Joshi, Bhalchandra V.,Kovac, Pavol,Hajduch, Jan,Kirk, Kenneth L.,Harden, T. Kendall,Jacobson, Kenneth A.
experimental part, p. 5298 - 5311 (2009/12/04)
The P2Y14 receptor, a nucleotide signaling protein, is activated by uridine-5′-diphosphoglucose 1 and other uracil nucleotides. We have determined that the glucose moiety of 1 is the most structurally permissive region for designing analogues of this P2Y14 agonist. For example, the carboxylate group of uridine-5′-diphosphoglucuronic acid proved to be suitable for flexible substitution by chain extension through an amide linkage. Functionalized congeners containing terminal 2-acylaminoethylamides prepared by this strategy retained P2Y14 activity, and molecular modeling predicted close proximity of this chain to the second extracellular loop of the receptor. In addition, replacement of glucose with other sugars did not diminish P2Y14 potency. For example, the [5′′]ribose derivative had an EC50 of 0.24 μM. Selective monofluorination of the glucose moiety indicated a role for the 2′′- and 6′′-hydroxyl groups of 1 in receptor recognition. The β-glucoside was twofold less potent than the native α-isomer, but methylene replacement of the 1′′-oxygen abolished activity. Replacement of the ribose ring system with cyclopentyl or rigid bicyclo[3.1.0]hexane groups abolished activity. Uridine-5′-diphosphoglucose also activates the P2Y2 receptor, but the 2-thio analogue and several of the potent modified-glucose analogues were P2Y14-selective.
Synthesis of UDP-glucose derivatives modified at the 3-OH as potential chain terminators of β-glucan biosynthesis
Danac, Ramona,Ball, Lucy,Gurr, Sarah J.,Fairbanks, Antony J.
, p. 1012 - 1022 (2008/09/20)
A series of UDP-d-glucose derivatives and precursors that have been modified at C-3 were synthesised from d-glucose as potential chain terminators of β-glucan biosynthesis. None of the UDP-derivatives or the precursors tested displayed significant anti-fungal activity in a series of germination assays on the dermatophyte Trichophyton rubrum.
4,6-O-benzylidene-directed β-mannopyranosylation and α-glucopyranosylation: The 2-deoxy-2-fluoro and 3-deoxy-3-fluoro series of donors and the importance of the O2-C2-C3-O3 interaction
Crich, David,Li, Linfeng
, p. 1681 - 1690 (2007/10/03)
A series of 4,6-O-benzylidene-protected 2-O-benzyl-3-deoxy-3-fluoro- and 3-O-benzyl-2-deoxy-2-fluorogluco-and mannopyranosyl thioglycosides were synthesized and their coupling reactions with a series of alcohols, on preactivation with 1-benzenesulfinylpip
