Literature DB >> 28943668

Acetone promoted 1,4-migration of an alkoxycarbonyl group on a syn-1,2-diamine.

Tanya Napolitano1, Shu-Yuan Cheng1,2, Brooke Nielsen1, Christopher Choi1, William Aguilar1, Manuel M Paz3, Anne-Marie Sapse1,4, Elise Champeil1,4.   

Abstract

A 2-protected cis-amino mitosene undergoes an irreversible acetone promoted isomerization and converts to the 1-isomer. Kinetic studies and DFT calculations of the reaction are reported. An organocatalytic mechanism is proposed, involving a covalent intermediate formed by reaction of the mitosene and acetone.

Entities:  

Keywords:  Acetone; Alkoxycarbonyl migration; Mitosene; Organocatalytic mechanism

Year:  2017        PMID： 28943668      PMCID： PMC5604470          DOI： 10.1016/j.tetlet.2016.12.047

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  18 in total

1.  Relative toxicities of DNA cross-links and monoadducts: new insights from studies of decarbamoyl mitomycin C and mitomycin C.

Authors:  Yolanda Palom; Gopinatha Suresh Kumar; Li-Qian Tang; Manuel M Paz; Steven M Musser; Sara Rockwell; Maria Tomasz
Journal:  Chem Res Toxicol       Date:  2002-11       Impact factor: 3.739

2.  Aziridinomitosanes via lactam cyclization.

Authors:  Susan D Wiedner; Edwin Vedejs
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

3.  Mapping DNA adducts of mitomycin C and decarbamoyl mitomycin C in cell lines using liquid chromatography/ electrospray tandem mass spectrometry.

Authors:  Manuel M Paz; Sweta Ladwa; Elise Champeil; Yanfeng Liu; Sara Rockwell; Ernest K Boamah; Jill Bargonetti; John Callahan; John Roach; Maria Tomasz
Journal:  Chem Res Toxicol       Date:  2008-12       Impact factor: 3.739

4.  Reaction of reductively activated mitomycin C with aqueous bicarbonate: Isolation and characterization of an oxazolidinone derivative of cis-1-hydroxy-2,7-diaminomitosene.

Authors:  Manuel M Paz
Journal:  Bioorg Med Chem Lett       Date:  2009-11-15       Impact factor: 2.823

5.  Synthesis of Mitomycin C and Decarbamoylmitomycin C N(2) deoxyguanosine-adducts.

Authors:  Elise Champeil; Shu-Yuan Cheng; Bik Tzu Huang; Marta Conchero-Guisan; Thibaut Martinez; Manuel M Paz; Anne-Marie Sapse
Journal:  Bioorg Chem       Date:  2016-02-11       Impact factor: 5.275

6.  Synthesis of an advanced intermediate en route to the mitomycin natural products.

Authors:  Amie L Williams; Jayasree M Srinivasan; Jeffrey N Johnston
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

7.  Synthesis of a major mitomycin C DNA adduct via a triaminomitosene.

Authors:  Elise Champeil; Manuel M Paz; Elaan Lukasiewicz; Wan S Kong; Stephanie Watson; Anne-Marie Sapse
Journal:  Bioorg Med Chem Lett       Date:  2012-09-25       Impact factor: 2.823

8.  Synthesis of an oligodeoxyribonucleotide adduct of mitomycin C by the postoligomerization method via a triamino mitosene.

Authors:  Elise Champeil; Manuel M Paz; Sweta Ladwa; Cristina C Clement; Andrzej Zatorski; Maria Tomasz
Journal:  J Am Chem Soc       Date:  2008-06-28       Impact factor: 15.419

9.  DNA adducts of decarbamoyl mitomycin C efficiently kill cells without wild-type p53 resulting from proteasome-mediated degradation of checkpoint protein 1.

Authors:  Ernest K Boamah; Angelika Brekman; Maria Tomasz; Natura Myeku; Maria Figueiredo-Pereira; Senyene Hunter; Joel Meyer; Rahul C Bhosle; Jill Bargonetti
Journal:  Chem Res Toxicol       Date:  2010-07-19       Impact factor: 3.739

10.  Mitomycin C and decarbamoyl mitomycin C induce p53-independent p21WAF1/CIP1 activation.

Authors:  Shu-Yuan Cheng; Jiwon Seo; Bik Tzu Huang; Tanya Napolitano; Elise Champeil
Journal:  Int J Oncol       Date:  2016-09-23       Impact factor: 5.650
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