Literature DB >> 19445490

Regiospecific syntheses of 6alpha-(1R-Hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid as mechanistic probes of class D beta-lactamases.

Sebastian A Testero1, Peter I O'Daniel, Qicun Shi, Mijoon Lee, Dusan Hesek, Akihiro Ishiwata, Bruce C Noll, Shahriar Mobashery.   

Abstract

The unique hydrophobic surface patches in class D beta-lactamases presented an opportunity for designing two compounds, 6alpha-(1R-hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid, as mechanistic probes of these enzymes. In a sequence of three synthetic steps from benzhydryl 6,6-dibromopenicillanate, the targeted compounds were prepared in a stereospecific manner.

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Year:  2009        PMID： 19445490      PMCID： PMC3297418          DOI： 10.1021/ol900668k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  High-resolution X-ray structure of an acyl-enzyme species for the class D OXA-10 beta-lactamase.

Authors:  Laurent Maveyraud; Dasantila Golemi-Kotra; Akihiro Ishiwata; Oussama Meroueh; Shahriar Mobashery; Jean-Pierre Samama
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

Review 2.  Bacterial resistance to beta-lactam antibiotics: compelling opportunism, compelling opportunity.

Authors:  Jed F Fisher; Samy O Meroueh; Shahriar Mobashery
Journal:  Chem Rev       Date:  2005-02       Impact factor: 60.622

3.  Aldol condensations of regiospecific penicillanate and cephalosporanate enolates. Hydroxyethylation at C-6 and C-7.

Authors:  F DiNinno; T R Beattie; B G Christensen
Journal:  J Org Chem       Date:  1977-09-02       Impact factor: 4.354

Review 4.  Kinship and diversification of bacterial penicillin-binding proteins and beta-lactamases.

Authors:  I Massova; S Mobashery
Journal:  Antimicrob Agents Chemother       Date:  1998-01       Impact factor: 5.191

5.  From penicillin to penem and carbapenem. VII. Synthesis and antibacterial activity of penem derivatives.

Authors:  K Fujimoto; Y Iwano; K Hirai; S Sugawara
Journal:  Chem Pharm Bull (Tokyo)       Date:  1986-03       Impact factor: 1.645

6.  Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.

Authors:  R L Rosati; L V Kapili; P Morrissey; J A Retsema
Journal:  J Med Chem       Date:  1990-01       Impact factor: 7.446

7.  Critical involvement of a carbamylated lysine in catalytic function of class D beta-lactamases.

Authors:  D Golemi; L Maveyraud; S Vakulenko; J P Samama; S Mobashery
Journal:  Proc Natl Acad Sci U S A       Date:  2001-11-27       Impact factor: 11.205

Review 8.  6-(hydroxyalkyl)penicillanates as probes for mechanisms of beta-lactamases.

Authors:  D Golemi; L Maveyraud; A Ishiwata; S Tranier; K Miyashita; T Nagase; I Massova; L Mourey; J P Samama; S Mobashery
Journal:  J Antibiot (Tokyo)       Date:  2000-10       Impact factor: 2.649

9.  Insights into class D beta-lactamases are revealed by the crystal structure of the OXA10 enzyme from Pseudomonas aeruginosa.

Authors:  L Maveyraud; D Golemi; L P Kotra; S Tranier; S Vakulenko; S Mobashery; J P Samama
Journal:  Structure       Date:  2000-12-15       Impact factor: 5.006

10.  Stereoselective reduction of alpha-bromopenicillanates by tributylphosphine.

Authors:  A Ishiwata; L P Kotra; K Miyashita; T Nagase; S Mobashery
Journal:  Org Lett       Date:  2000-09-07       Impact factor: 6.005
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  4 in total

1.  Hydrolytic mechanism of OXA-58 enzyme, a carbapenem-hydrolyzing class D β-lactamase from Acinetobacter baumannii.

Authors:  Vidhu Verma; Sebastian A Testero; Kaveh Amini; William Wei; Jerome Liu; Naresh Balachandran; Tharseekan Monoharan; Siobhan Stynes; Lakshmi P Kotra; Dasantila Golemi-Kotra
Journal:  J Biol Chem       Date:  2011-08-31       Impact factor: 5.157

2.  Modifications of the C6-substituent of penicillin sulfones with the goal of improving inhibitor recognition and efficacy.

Authors:  Micheal Nottingham; Christopher R Bethel; Sundar Ram Reddy Pagadala; Emily Harry; Abishai Pinto; Zachary A Lemons; Sarah M Drawz; Focco van den Akker; Paul R Carey; Robert A Bonomo; John D Buynak
Journal:  Bioorg Med Chem Lett       Date:  2010-11-05       Impact factor: 2.823

Review 3.  Acyclic Twisted Amides.

Authors:  Guangrong Meng; Jin Zhang; Michal Szostak
Journal:  Chem Rev       Date:  2021-08-18       Impact factor: 72.087

4.  Modified Penicillin Molecule with Carbapenem-Like Stereochemistry Specifically Inhibits Class C β-Lactamases.

Authors:  Xuehua Pan; Yunjiao He; Tianfeng Chen; Kin-Fai Chan; Yanxiang Zhao
Journal:  Antimicrob Agents Chemother       Date:  2017-11-22       Impact factor: 5.191
  4 in total

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