Literature DB >> 35431351

A Convenient Protecting Group for Uridine Ureido Nitrogen: (4,4'-Bisfluorophenyl)methoxymethyl group.

Katsuhiko Mitachi1, David Mingle1, Michio Kurosu1.   

Abstract

(4,4'-Bisfluorophenyl)methoxymethyl (BFPM) group of uridine ureido nitrogen shows good relative stability in a variety of chemical transformation reactions for uridine. The BFPM group can be cleaved via 2% of TFA in CH2Cl2 without affecting the Boc group.

Entities:  

Keywords:  (Bis(4-fluorophenyl)methoxy)methyl group; Chemical transformations; Diarylmethoxymethyl group; Ureido nitrogen; Uridine; muraymycin synthesis

Year:  2021        PMID： 35431351      PMCID： PMC9009825          DOI： 10.1055/a-1464-2473

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   2.969


  32 in total

1.  Polymer-supported (2,6-dichloro- 4-alkoxyphenyl)(2,4-dichlorophenyl)methanol: a new linker for solid-phase organic synthesis.

Authors:  Michio Kurosu; Kallolmay Biswas; Dean C Crick
Journal:  Org Lett       Date:  2007-02-21       Impact factor: 6.005

2.  Structure-based drug discovery by targeting N-glycan biosynthesis, dolichyl-phosphate N-acetylglucosaminephosphotransferase.

Authors:  Michio Kurosu
Journal:  Future Med Chem       Date:  2019-03-25       Impact factor: 3.808

3.  Inhibition of N-Glycosylation towards Novel Anti-Cancer Chemotherapeutics.

Authors:  Michio Kurosu
Journal:  J Mol Pharm Org Process Res       Date:  2018-01-12

Review 4.  Antimicrobial nucleoside antibiotics targeting cell wall assembly: recent advances in structure-function studies and nucleoside biosynthesis.

Authors:  Michael Winn; Rebecca J M Goss; Ken-ichi Kimura; Timothy D H Bugg
Journal:  Nat Prod Rep       Date:  2009-12-16       Impact factor: 13.423

5.  A new protecting group and linker for uridine ureido nitrogen.

Authors:  Yong Wang; Michio Kurosu
Journal:  Tetrahedron       Date:  2012-04-09       Impact factor: 2.457

Review 6.  Metabolism, Biochemical Actions, and Chemical Synthesis of Anticancer Nucleosides, Nucleotides, and Base Analogs.

Authors:  Jadd Shelton; Xiao Lu; Joseph A Hollenbaugh; Jong Hyun Cho; Franck Amblard; Raymond F Schinazi
Journal:  Chem Rev       Date:  2016-11-23       Impact factor: 60.622

7.  Muraymycins, novel peptidoglycan biosynthesis inhibitors: synthesis and SAR of their analogues.

Authors:  Ayako Yamashita; Emily Norton; Peter J Petersen; Beth A Rasmussen; Guy Singh; Youjin Yang; Tarek S Mansour; Douglas M Ho
Journal:  Bioorg Med Chem Lett       Date:  2003-10-06       Impact factor: 2.823

8.  Discovery of a capuramycin analog that kills nonreplicating Mycobacterium tuberculosis and its synergistic effects with translocase I inhibitors.

Authors:  Shajila Siricilla; Katsuhiko Mitachi; Bajoie Wan; Scott G Franzblau; Michio Kurosu
Journal:  J Antibiot (Tokyo)       Date:  2014-10-01       Impact factor: 2.649

Review 9.  Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents.

Authors:  Daniel Wiegmann; Stefan Koppermann; Marius Wirth; Giuliana Niro; Kristin Leyerer; Christian Ducho
Journal:  Beilstein J Org Chem       Date:  2016-04-22       Impact factor: 2.883

10.  A straightforward diphenylmethyl protection method and deprotection of some pyrimidine nucleosides.

Authors:  Milind Saudi; Arthur van Aerschot
Journal:  Molecules       Date:  2013-07-18       Impact factor: 4.411
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  1 in total

1.  Concise Synthesis of Tunicamycin V and Discovery of a Cytostatic DPAGT1 Inhibitor.

Authors:  Katsuhiko Mitachi; David Mingle; Wendy Effah; Antonio Sánchez-Ruiz; Kirk E Hevener; Ramesh Narayanan; William M Clemons; Francisco Sarabia; Michio Kurosu
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-10       Impact factor: 16.823
  1 in total

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