Literature DB >> 18375129

S-Ribosylhomocysteine analogues with the carbon-5 and sulfur atoms replaced by a vinyl or (fluoro)vinyl unit.

Stanislaw F Wnuk1, Jennifer Lalama, Craig A Garmendia, Jenay Robert, Jinge Zhu, Dehua Pei.   

Abstract

Treatment of the protected ribose or xylose 5-aldehyde with sulfonyl-stabilized fluorophosphonate gave (fluoro)vinyl sulfones. Stannyldesulfonylation followed by iododestannylation afforded 5,6-dideoxy-6-fluoro-6-iodo-d-ribo or xylo-hex-5-enofuranoses. Coupling of the hexenofuranoses with alkylzinc bromides gave 10-carbon ribosyl- and xylosylhomocysteine analogues incorporating a fluoroalkene. The fluoroalkenyl and alkenyl analogues were evaluated for inhibition of Bacillus subtilis S-ribosylhomocysteinase (LuxS). One of the compounds, 3,5,6-trideoxy-6-fluoro-d-erythro-hex-5-enofuranose, acted as a competitive inhibitor of moderate potency (K(I)=96microM).

Entities:  

Mesh：

Substances：

Year:  2008        PMID： 18375129      PMCID： PMC2443868          DOI： 10.1016/j.bmc.2008.03.028

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  39 in total

Review 1.  Quorum sensing: cell-to-cell communication in bacteria.

Authors:  Christopher M Waters; Bonnie L Bassler
Journal:  Annu Rev Cell Dev Biol       Date:  2005       Impact factor: 13.827

2.  Small molecule inhibitors of bacterial quorum sensing and biofilm formation.

Authors:  Grant D Geske; Rachel J Wezeman; Adam P Siegel; Helen E Blackwell
Journal:  J Am Chem Soc       Date:  2005-09-21       Impact factor: 15.419

3.  Novel S-ribosylhomocysteine analogues as potential inhibitors of LuxS enzyme.

Authors:  Stanislaw F Wnuk; Jennifer Lalama; Jenay Robert; Craig A Garmendia
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2007       Impact factor: 1.381

4.  Widely applicable Pd-catalyzed trans-selective monoalkylation of unactivated 1,1-dichloro-1-alkenes and Pd-catalyzed second substitution for the selective synthesis of E or Z trisubstituted alkenes.

Authors:  Ze Tan; Ei-Ichi Negishi
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-23       Impact factor: 15.336

5.  Design and synthesis of substrate and intermediate analogue inhibitors of S-ribosylhomocysteinase.

Authors:  Gang Shen; Rakhi Rajan; Jinge Zhu; Charles E Bell; Dehua Pei
Journal:  J Med Chem       Date:  2006-05-18       Impact factor: 7.446

6.  Nucleic acid related compounds. 84. Synthesis of 6'-(E and Z)-halohomovinyl derivatives of adenosine, inactivation of S-adenosyl-L-homocysteine hydrolase, and correlation of anticancer and antiviral potencies with enzyme inhibition.

Authors:  S F Wnuk; C S Yuan; R T Borchardt; J Balzarini; E De Clercq; M J Robins
Journal:  J Med Chem       Date:  1994-10-14       Impact factor: 7.446

7.  An expeditious synthesis of DPD and boron binding studies.

Authors:  Martin F Semmelhack; Shawn R Campagna; Michael J Federle; Bonnie L Bassler
Journal:  Org Lett       Date:  2005-02-17       Impact factor: 6.005

8.  Suzuki-miyaura cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN.

Authors:  Frédéric Liron; Céline Fosse; Alban Pernolet; Emmanuel Roulland
Journal:  J Org Chem       Date:  2007-02-21       Impact factor: 4.354

9.  Catalytic mechanism of S-ribosylhomocysteinase (LuxS): stereochemical course and kinetic isotope effect of proton transfer reactions.

Authors:  Jinge Zhu; Reena Patel; Dehua Pei
Journal:  Biochemistry       Date:  2004-08-10       Impact factor: 3.162

10.  Catalytic mechanism of S-ribosylhomocysteinase (LuxS): direct observation of ketone intermediates by 13C NMR spectroscopy.

Authors:  Jinge Zhu; Xubo Hu; Eric Dizin; Dehua Pei
Journal:  J Am Chem Soc       Date:  2003-11-05       Impact factor: 15.419
View more
  10 in total

1.  Application of germyldesulfonylation reactions to the synthesis of germanium-containing nucleoside analogues.

Authors:  Stanislaw F Wnuk; Pablo R Sacasa; Jorge Restrepo
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2009-05       Impact factor: 1.381

Review 2.  Exploiting quorum sensing to confuse bacterial pathogens.

Authors:  Breah LaSarre; Michael J Federle
Journal:  Microbiol Mol Biol Rev       Date:  2013-03       Impact factor: 11.056

3.  Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring.

Authors:  Venkata L A Malladi; Adam J Sobczak; Tiffany M Meyer; Dehua Pei; Stanislaw F Wnuk
Journal:  Bioorg Med Chem       Date:  2011-07-28       Impact factor: 3.641

4.  Screening of Actinobacillus pleuropneumoniae LuxS inhibitors.

Authors:  Lu Li; Lili Sun; Yunfeng Song; Xinjuan Wu; Xuan Zhou; Ziduo Liu; Rui Zhou
Journal:  Curr Microbiol       Date:  2013-06-07       Impact factor: 2.188

5.  Practical, efficient, and broadly applicable synthesis of readily differentiable vicinal diboronate compounds by catalytic three-component reactions.

Authors:  Suttipol Radomkit; Zhenxing Liu; Anna Closs; Malte S Mikus; Amir H Hoveyda
Journal:  Tetrahedron       Date:  2017-05-20       Impact factor: 2.457

6.  Synthesis of 5'-functionalized nucleosides: S-Adenosylhomocysteine analogues with the carbon-5' and sulfur atoms replaced by a vinyl or halovinyl unit.

Authors:  Stanislaw F Wnuk; Pablo R Sacasa; Elzbieta Lewandowska; Daniela Andrei; Sumin Cai; Ronald T Borchardt
Journal:  Bioorg Med Chem       Date:  2008-04-12       Impact factor: 3.641

7.  A naturally occurring brominated furanone covalently modifies and inactivates LuxS.

Authors:  Tianzhu Zang; Bobby W K Lee; Lisa M Cannon; Kathryn A Ritter; Shujia Dai; Dacheng Ren; Thomas K Wood; Zhaohui Sunny Zhou
Journal:  Bioorg Med Chem Lett       Date:  2009-09-03       Impact factor: 2.823

8.  Kinetically controlled E-selective catalytic olefin metathesis.

Authors:  Thach T Nguyen; Ming Joo Koh; Xiao Shen; Filippo Romiti; Richard R Schrock; Amir H Hoveyda
Journal:  Science       Date:  2016-04-29       Impact factor: 47.728

9.  Inhibition of S-ribosylhomocysteinase (LuxS) by substrate analogues modified at the ribosyl C-3 position.

Authors:  Stanislaw F Wnuk; Jenay Robert; Adam J Sobczak; Brandon P Meyers; Venkata L A Malladi; Jinge Zhu; Bhaskar Gopishetty; Dehua Pei
Journal:  Bioorg Med Chem       Date:  2009-07-26       Impact factor: 3.641

Review 10.  Interference With Quorum-Sensing Signal Biosynthesis as a Promising Therapeutic Strategy Against Multidrug-Resistant Pathogens.

Authors:  Osmel Fleitas Martínez; Pietra Orlandi Rigueiras; Állan da Silva Pires; William Farias Porto; Osmar Nascimento Silva; Cesar de la Fuente-Nunez; Octavio Luiz Franco
Journal:  Front Cell Infect Microbiol       Date:  2019-02-05       Impact factor: 5.293
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.