Literature DB >> 22711936

A new protecting group and linker for uridine ureido nitrogen.

Yong Wang1, Michio Kurosu.   

Abstract

(2,6-Dichloro-4-methoxyphenyl) (2,4,6-trichlorophenyl) methoxymethyl chloride [1, monomethoxydiphenylmethoxylmethyl chloroide (MDPM-Cl)] shows a significant relative stability and 1 reacts with uridine ureido nitrogen in the presence of DBU to form the corresponding protected uridine 8 in 95% yield. The MDPM-protected uridines are stable to a wide variety of conditions utilized for the synthesis of analogs of capuramycin and muraymycins. Significantly, the MDPM protecting group can conveniently be deprotected by using 30% TFA in CH(2)Cl(2). In addition, polymer-bound MDPM-Cl 23 is useful for immobilization of uridine derivatives.

Entities:  

Year:  2012        PMID: 22711936      PMCID: PMC3375706          DOI: 10.1016/j.tet.2012.03.121

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  12 in total

1.  Synthesis of analogues of the O-beta-D-ribofuranosyl nucleoside moiety of liposidomycins. Part 1: contribution of the amino group and the uracil moiety upon the inhibition of MraY.

Authors:  C Dini; N Drochon; S Feteanu; J C Guillot; C Peixoto; J Aszodi
Journal:  Bioorg Med Chem Lett       Date:  2001-02-26       Impact factor: 2.823

2.  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

3.  In vitro antimycobacterial activities of capuramycin analogues.

Authors:  Venkata M Reddy; Leo Einck; Carol A Nacy
Journal:  Antimicrob Agents Chemother       Date:  2007-12-10       Impact factor: 5.191

Review 4.  UGT genomic diversity: beyond gene duplication.

Authors:  Chantal Guillemette; Eric Lévesque; Mario Harvey; Judith Bellemare; Vincent Menard
Journal:  Drug Metab Rev       Date:  2010-02       Impact factor: 4.518

Review 5.  MraY Inhibitors as Novel Antibacterial Agents.

Authors:  Christophe Dini
Journal:  Curr Top Med Chem       Date:  2005       Impact factor: 3.295

6.  Stereoselective synthesis of uridine-derived nucleosyl amino acids.

Authors:  Anatol P Spork; Daniel Wiegmann; Markus Granitzka; Dietmar Stalke; Christian Ducho
Journal:  J Org Chem       Date:  2011-11-21       Impact factor: 4.354

7.  New chiral derivatizing agents: convenient determination of absolute configurations of free amino acids by 1H NMR.

Authors:  Michio Kurosu; Kai Li
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

8.  Fine synthetic nucleoside chemistry based on nucleoside natural products synthesis.

Authors:  Satoshi Ichikawa
Journal:  Chem Pharm Bull (Tokyo)       Date:  2008-08       Impact factor: 1.645

9.  Concise synthesis of capuramycin.

Authors:  Michio Kurosu; Kai Li; Dean C Crick
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

Review 10.  Phospho-MurNAc-pentapeptide translocase (MraY) as a target for antibacterial agents and antibacterial proteins.

Authors:  Timothy D H Bugg; Adrian J Lloyd; David I Roper
Journal:  Infect Disord Drug Targets       Date:  2006-06
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  9 in total

1.  Improved synthesis of capuramycin and its analogues.

Authors:  Yong Wang; Shajila Siricilla; Bilal A Aleiwi; Michio Kurosu
Journal:  Chemistry       Date:  2013-09-06       Impact factor: 5.236

2.  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

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

Authors:  Katsuhiko Mitachi; David Mingle; Michio Kurosu
Journal:  Synthesis (Stuttg)       Date:  2021-03-25       Impact factor: 2.969

4.  Stereocontrolled Total Synthesis of Muraymycin D1 Having a Dual Mode of Action against Mycobacterium tuberculosis.

Authors:  Katsuhiko Mitachi; Bilal A Aleiwi; Christopher M Schneider; Shajila Siricilla; Michio Kurosu
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

5.  One-pot protection-glycosylation reactions for synthesis of lipid II analogues.

Authors:  Katsuhiko Mitachi; Priya Mohan; Shajila Siricilla; Michio Kurosu
Journal:  Chemistry       Date:  2014-03-12       Impact factor: 5.236

6.  Backbone-Anchoring, Solid-Phase Synthesis Strategy To Access a Library of Peptidouridine-Containing Small Molecules.

Authors:  Christine A Arbour; Barbara Imperiali
Journal:  Org Lett       Date:  2022-03-10       Impact factor: 6.072

7.  Novel FR-900493 Analogues That Inhibit the Outgrowth of Clostridium difficile Spores.

Authors:  Katsuhiko Mitachi; Hyun Gi Yun; Sara M Kurosu; Shakiba Eslamimehr; Maddie R Lemieux; Lada Klaić; William M Clemons; Michio Kurosu
Journal:  ACS Omega       Date:  2018-02-09

Review 8.  Biosynthetic and Synthetic Strategies for Assembling Capuramycin-Type Antituberculosis Antibiotics.

Authors:  Ashley L Biecker; Xiaodong Liu; Jon S Thorson; Zhaoyong Yang; Steven G Van Lanen
Journal:  Molecules       Date:  2019-01-25       Impact factor: 4.411

9.  A practical synthesis of a novel DPAGT1 inhibitor, aminouridyl phenoxypiperidinbenzyl butanamide (APPB) for in vivo studies.

Authors:  Katsuhiko Mitachi; Shou M Kurosu; Cody D Gillman; Hyun Gi Yun; William M Clemons; Michio Kurosu
Journal:  MethodsX       Date:  2019-09-27
  9 in total

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