Literature DB >> 30063360

Synthesis of 5-Methylene-2-pyrrolones.

Marco Paolo Jacinto1, Patricio Pichling1, Marc M Greenberg1.   

Abstract

A facile, one-pot synthetic method for the synthesis of 5-methylene-2-pyrrolones (5MPs) from inexpensive furfuryl acetate is described. Bromine oxidation and trapping of the in situ generated 1,4-dicarbonyl compound by a primary amine provided the corresponding 5MPs in 50-69% yield.

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Year:  2018        PMID： 30063360      PMCID： PMC6132240          DOI： 10.1021/acs.orglett.8b02030

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


  14 in total

1.  Cross-Linking Furan-Modified Kisspeptin-10 to the KISS Receptor.

Authors:  Willem Vannecke; Christophe Ampe; Marleen Van Troys; Massimiliano Beltramo; Annemieke Madder
Journal:  ACS Chem Biol       Date:  2017-07-17       Impact factor: 5.100

2.  Photochemical generation of oligodeoxynucleotide containing a C4'-oxidized abasic site and its efficient amine modification: dependence on structure and microenvironment.

Authors:  Kazuteru Usui; Mariko Aso; Mitsuhiro Fukuda; Hiroshi Suemune
Journal:  J Org Chem       Date:  2007-12-07       Impact factor: 4.354

3.  Toxicity inspired cross-linking for probing DNA-peptide interactions.

Authors:  Lieselot L G Carrette; Takashi Morii; Annemieke Madder
Journal:  Bioconjug Chem       Date:  2013-11-19       Impact factor: 4.774

4.  Synthesis and incorporation of a furan-modified adenosine building block for DNA interstrand crosslinking.

Authors:  Anup M Jawalekar; Marieke Op de Beeck; Floris L van Delft; Annemieke Madder
Journal:  Chem Commun (Camb)       Date:  2011-02-02       Impact factor: 6.222

5.  Photochemical generation of C4'-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification.

Authors:  Mariko Aso; Kazuteru Usui; Mitsuhiro Fukuda; Yoshie Kakihara; Tsuyoshi Goromaru; Hiroshi Suemune
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

6.  Unprecedented C-selective interstrand cross-linking through in situ oxidation of furan-modified oligodeoxynucleotides.

Authors:  Marieke Op de Beeck; Annemieke Madder
Journal:  J Am Chem Soc       Date:  2010-12-16       Impact factor: 15.419

7.  Long patch base excision repair compensates for DNA polymerase β inactivation by the C4'-oxidized abasic site.

Authors:  Aaron C Jacobs; Cortney R Kreller; Marc M Greenberg
Journal:  Biochemistry       Date:  2010-12-14       Impact factor: 3.162

8.  Fine-tuning furan toxicity: fast and quantitative DNA interchain cross-link formation upon selective oxidation of a furan containing oligonucleotide.

Authors:  Sami Halila; Trinidad Velasco; Pierre De Clercq; Annemieke Madder
Journal:  Chem Commun (Camb)       Date:  2005-01-04       Impact factor: 6.222

9.  The multiple Maillard reactions of ribose and deoxyribose sugars and sugar phosphates.

Authors:  Admire Munanairi; Steven K O'Banion; Ryan Gamble; Elizabeth Breuer; Andrew W Harris; Roger K Sandwick
Journal:  Carbohydr Res       Date:  2007-08-19       Impact factor: 2.104

10.  Furan oxidation based cross-linking: a new approach for the study and targeting of nucleic acid and protein interactions.

Authors:  L L G Carrette; E Gyssels; N De Laet; A Madder
Journal:  Chem Commun (Camb)       Date:  2015-12-17       Impact factor: 6.222
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  2 in total

1.  Intracellular Formation of a DNA Damage-Induced, Histone Post-Translational Modification Following Bleomycin Treatment.

Authors:  Marco Paolo Jacinto; Stephen D Fried; Marc M Greenberg
Journal:  J Am Chem Soc       Date:  2022-04-25       Impact factor: 16.383

2.  Cysteine-specific protein multi-functionalization and disulfide bridging using 3-bromo-5-methylene pyrrolones.

Authors:  Yingqian Zhang; Chuanlong Zang; Guoce An; Mengdi Shang; Zenghui Cui; Gong Chen; Zhen Xi; Chuanzheng Zhou
Journal:  Nat Commun       Date:  2020-02-21       Impact factor: 14.919
  2 in total

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