Literature DB >> 19763307

Nucleoside triphosphate mimicry: a sugar triazolyl nucleoside as an ATP-competitive inhibitor of B. anthracis pantothenate kinase.

Andrew S Rowan1, Nathan I Nicely, Nicola Cochrane, Wjatschesslaw A Wlassoff, Al Claiborne, Chris J Hamilton.   

Abstract

The synthesis of a library of nucleoside triphosphate mimetics is described where the Mg(2+) chelated triphosphate sidechain is replaced by an uncharged methylene-triazole linked monosaccharide sidechain. The compounds have been evaluated as inhibitors of Bacillus anthracis pantothenate kinase and a competitive inhibitor has been identified with a K(i) that is 3-fold lower than the K(m) value of ATP.

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Year:  2009        PMID： 19763307      PMCID： PMC6074028          DOI： 10.1039/b909729e

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  20 in total

1.  Characterization of a new pantothenate kinase isoform from Helicobacter pylori.

Authors:  Leisl A Brand; Erick Strauss
Journal:  J Biol Chem       Date:  2005-03-28       Impact factor: 5.157

2.  A search for pyrophosphate mimics for the development of substrates and inhibitors of glycosyltransferases.

Authors:  R Wang; D H Steensma; Y Takaoka; J W Yun; T Kajimoto; C H Wong
Journal:  Bioorg Med Chem       Date:  1997-04       Impact factor: 3.641

3.  Crystal structure of a type III pantothenate kinase: insight into the mechanism of an essential coenzyme A biosynthetic enzyme universally distributed in bacteria.

Authors:  Kun Yang; Yvonne Eyobo; Leisl A Brand; Dariusz Martynowski; Diana Tomchick; Erick Strauss; Hong Zhang
Journal:  J Bacteriol       Date:  2006-08       Impact factor: 3.490

4.  Structure of the type III pantothenate kinase from Bacillus anthracis at 2.0 A resolution: implications for coenzyme A-dependent redox biology.

Authors:  Nathan I Nicely; Derek Parsonage; Carleitta Paige; Gerald L Newton; Robert C Fahey; Roberta Leonardi; Suzanne Jackowski; T Conn Mallett; Al Claiborne
Journal:  Biochemistry       Date:  2007-02-27       Impact factor: 3.162

5.  Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors.

Authors:  Kar Kheng Yeoh; Terry D Butters; Brendan L Wilkinson; Antony J Fairbanks
Journal:  Carbohydr Res       Date:  2009-01-17       Impact factor: 2.104

Review 6.  Recent advances in antimicrobial nucleoside antibiotics targeting cell wall biosynthesis.

Authors:  Ken-ichi Kimura; Timothy D H Bugg
Journal:  Nat Prod Rep       Date:  2003-04       Impact factor: 13.423

7.  Synthesis and high-throughput screening of N-acetyl-beta-hexosaminidase inhibitor libraries targeting osteoarthritis.

Authors:  Junjie Liu; Mehdi M D Numa; Haitian Liu; Shi-Jung Huang; Pamela Sears; Alexander R Shikhman; Chi-Huey Wong
Journal:  J Org Chem       Date:  2004-09-17       Impact factor: 4.354

8.  Adenosine-anchored triphosphate subsite probing: distinguishing between HER-2 and HER-4 tyrosine protein kinases.

Authors:  Fei Liu; Eric F Johnson; David J Austin; Karen S Anderson
Journal:  Bioorg Med Chem Lett       Date:  2003-10-20       Impact factor: 2.823

9.  Design, synthesis, and molecular modeling studies of 5'-deoxy-5'-ureidoadenosine: 5'-ureido group as multiple hydrogen bonding donor in the active site of S-adenosylhomocysteine hydrolase.

Authors:  Ting Wang; Hyun Joo Lee; Dilip K Tosh; Hea Ok Kim; Shantanu Pal; Sun Choi; Yoonji Lee; Hyung Ryong Moon; Long Xuan Zhao; Kang Man Lee; Lak Shin Jeong
Journal:  Bioorg Med Chem Lett       Date:  2007-06-08       Impact factor: 2.823

10.  Triazole-linked analogue of deoxyribonucleic acid ((TL)DNA): design, synthesis, and double-strand formation with natural DNA.

Authors:  Hiroyuki Isobe; Tomoko Fujino; Naomi Yamazaki; Marine Guillot-Nieckowski; Eiichi Nakamura
Journal:  Org Lett       Date:  2008-07-26       Impact factor: 6.005
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  12 in total

1.  Inositol 1,3,4,5,6-pentakisphosphate 2-kinase is a distant IPK member with a singular inositide binding site for axial 2-OH recognition.

Authors:  Beatriz González; Jose Ignacio Baños-Sanz; Maider Villate; Charles Alistair Brearley; Julia Sanz-Aparicio
Journal:  Proc Natl Acad Sci U S A       Date:  2010-05-07       Impact factor: 11.205

2.  Conformational changes in inositol 1,3,4,5,6-pentakisphosphate 2-kinase upon substrate binding: role of N-terminal lobe and enantiomeric substrate preference.

Authors:  José Ignacio Baños-Sanz; Julia Sanz-Aparicio; Hayley Whitfield; Chris Hamilton; Charles A Brearley; Beatriz González
Journal:  J Biol Chem       Date:  2012-06-28       Impact factor: 5.157

3.  Synthesis, thermal properties, and cytotoxicity evaluation of hydrocarbon and fluorocarbon alkyl β-D-xylopyranoside surfactants.

Authors:  Wenjin Xu; Gifty Osei-Prempeh; Carolina Lema; E Davis Oldham; Renato J Aguilera; Sean Parkin; Stephen E Rankin; Barbara L Knutson; Hans-Joachim Lehmler
Journal:  Carbohydr Res       Date:  2011-12-09       Impact factor: 2.104

4.  Alkyne-azide click reaction catalyzed by metallic copper under ultrasound.

Authors:  Pedro Cintas; Alessandro Barge; Silvia Tagliapietra; Luisa Boffa; Giancarlo Cravotto
Journal:  Nat Protoc       Date:  2010-03-04       Impact factor: 13.491

5.  Synthesis, surface properties, and biocompatibility of 1,2,3-triazole-containing alkyl β-D-xylopyranoside surfactants.

Authors:  E Davis Oldham; Srivenu Seelam; Carolina Lema; Renato J Aguilera; Jennifer Fiegel; Stephen E Rankin; Barbara L Knutson; Hans-Joachim Lehmler
Journal:  Carbohydr Res       Date:  2013-06-28       Impact factor: 2.104

6.  C-5'-Triazolyl-2'-oxa-3'-aza-4'a-carbanucleosides: Synthesis and biological evaluation.

Authors:  Roberto Romeo; Caterina Carnovale; Salvatore V Giofrè; Maria A Chiacchio; Adriana Garozzo; Emanuele Amata; Giovanni Romeo; Ugo Chiacchio
Journal:  Beilstein J Org Chem       Date:  2015-03-09       Impact factor: 2.883

7.  Synthesis and Anticancer Activity of 4β-Triazole-podophyllotoxin Glycosides.

Authors:  Cheng-Ting Zi; Gen-Tao Li; Yan Li; Jun Zhou; Zhong-Tao Ding; Zi-Hua Jiang; Jiang-Miao Hu
Journal:  Nat Prod Bioprospect       Date:  2015-04-14

8.  Cytotoxic activity of triazole-containing alkyl β-D-glucopyranosides on a human T-cell leukemia cell line.

Authors:  Edward Davis Oldham; Larissa M Nunes; Armando Varela-Ramirez; Stephen E Rankin; Barbara L Knutson; Renato J Aguilera; Hans-Joachim Lehmler
Journal:  Chem Cent J       Date:  2015-02-01       Impact factor: 4.215

9.  Anti-Tick-Borne Encephalitis Virus Activity of Novel Uridine Glycoconjugates Containing Amide or/and 1,2,3-Triazole Moiety in the Linker Structure.

Authors:  Gabriela Brzuska; Gabriela Pastuch-Gawolek; Monika Krawczyk; Boguslaw Szewczyk; Ewelina Krol
Journal:  Pharmaceuticals (Basel)       Date:  2020-12-13

10.  Design and Synthesis of α-Anomeric Diacetylene-Containing Glycosides as Photopolymerizable Molecular Gelators.

Authors:  Guijun Wang; Dan Wang; Anji Chen; Ifeanyi S Okafor; Lalith Palitha Samankumara
Journal:  ACS Omega       Date:  2022-03-21
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