Literature DB >> 21528870

Asymmetric enzymatic glycosylation of mitoxantrone.

Maoquan Zhou1, Jon S Thorson.   

Abstract

Using a uniquely promiscuous engineered glycosyltransferase (GT) derived from the macrolide-inactivating GT OleD, a single-step asymmetric glucosylation of one 'arm' of the drug mitoxantrone was efficiently achieved in high stereo- and regiospecificity. The synthesis, structural elucidation, and anticancer activity of the corresponding mitoxantrone 4'-β-D-glucoside are described.

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Year:  2011        PMID： 21528870      PMCID： PMC3099400          DOI： 10.1021/ol200977u

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


  42 in total

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2.  Expanding the promiscuity of a natural-product glycosyltransferase by directed evolution.

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3.  A high-throughput fluorescence-based glycosyltransferase screen and its application in directed evolution.

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4.  Optimizing glycosyltransferase specificity via "hot spot" saturation mutagenesis presents a catalyst for novobiocin glycorandomization.

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5.  Synthesis of DNA-directed pyrrolidinyl and piperidinyl confined alkylating chloroalkylaminoanthraquinones: potential for development of tumor-selective N-oxides.

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6.  A theoretical study on interactions between mitoxantrone as an anticancer drug and DNA: application in drug design.

Authors:  Siavash Riahi; Mohammad Reza Ganjali; Rassoul Dinarvand; Sanaz Karamdoust; Kowsar Bagherzadeh; Parviz Norouzi
Journal:  Chem Biol Drug Des       Date:  2008-03-29       Impact factor: 2.817

7.  Pixantrone (BBR 2778) has reduced cardiotoxic potential in mice pretreated with doxorubicin: comparative studies against doxorubicin and mitoxantrone.

Authors:  Ennio Cavalletti; Luca Crippa; Patrizia Mainardi; Norberto Oggioni; Rosanna Cavagnoli; Ornella Bellini; Franca Sala
Journal:  Invest New Drugs       Date:  2007-06       Impact factor: 3.850

8.  Synthesis, DNA binding, and cytotoxicity of 1,4-bis(2-amino-ethylamino)anthraquinone-amino acid conjugates.

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Journal:  Bioorg Med Chem       Date:  2007-10-10       Impact factor: 3.641

9.  The crystal structure of two macrolide glycosyltransferases provides a blueprint for host cell antibiotic immunity.

Authors:  David N Bolam; Shirley Roberts; Mark R Proctor; Johan P Turkenburg; Eleanor J Dodson; Carlos Martinez-Fleites; Min Yang; Benjamin G Davis; Gideon J Davies; Harry J Gilbert
Journal:  Proc Natl Acad Sci U S A       Date:  2007-03-21       Impact factor: 11.205

10.  Pixantrone can be activated by formaldehyde to generate a potent DNA adduct forming agent.

Authors:  Ben J Evison; Oula C Mansour; Ernesto Menta; Don R Phillips; Suzanne M Cutts
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  8 in total

Review 1.  Recent biotechnological progress in enzymatic synthesis of glycosides.

Authors:  Nguyen Huy Thuan; Jae Kyung Sohng
Journal:  J Ind Microbiol Biotechnol       Date:  2013-09-05       Impact factor: 3.346

2.  OleD Loki as a Catalyst for Tertiary Amine and Hydroxamate Glycosylation.

Authors:  Ryan R Hughes; Khaled A Shaaban; Jianjun Zhang; Hongnan Cao; George N Phillips; Jon S Thorson
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3.  A simple strategy for glycosyltransferase-catalyzed aminosugar nucleotide synthesis.

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4.  Identification of Neuroprotective Spoxazomicin and Oxachelin Glycosides via Chemoenzymatic Glycosyl-Scanning.

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Journal:  J Nat Prod       Date:  2016-12-28       Impact factor: 4.050

5.  Probing the regiospecificity of enzyme-catalyzed steroid glycosylation.

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6.  Assessing the regioselectivity of OleD-catalyzed glycosylation with a diverse set of acceptors.

Authors:  Maoquan Zhou; Adel Hamza; Chang-Guo Zhan; Jon S Thorson
Journal:  J Nat Prod       Date:  2013-01-29       Impact factor: 4.050

7.  OleD Loki as a Catalyst for Hydroxamate Glycosylation.

Authors:  Ryan R Hughes; Khaled A Shaaban; Larissa V Ponomareva; Jamie Horn; Chunhui Zhang; Chang-Guo Zhan; S Randal Voss; Markos Leggas; Jon S Thorson
Journal:  Chembiochem       Date:  2019-11-26       Impact factor: 3.164

8.  Probing the stereoselectivity of OleD-catalyzed glycosylation of cardiotonic steroids.

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Journal:  RSC Adv       Date:  2018-01-30       Impact factor: 4.036
  8 in total

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