Literature DB >> 19405507

Concise synthesis of capuramycin.

Michio Kurosu1, Kai Li, Dean C Crick.   

Abstract

A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4'',5''-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with >30% overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin.

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Year:  2009        PMID： 19405507      PMCID： PMC4784474          DOI： 10.1021/ol900458w

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


  25 in total

1.  District-randomized phased implementation: strengthening the evidence base for cotrimoxazole for HIV-positive tuberculosis patients.

Authors:  Peter Godfrey-Faussett
Journal:  AIDS       Date:  2003-05-02       Impact factor: 4.177

2.  Identification of active-site inhibitors of MurG using a generalizable, high-throughput glycosyltransferase screen.

Authors:  Jeremiah S Helm; Yanan Hu; Lan Chen; Ben Gross; Suzanne Walker
Journal:  J Am Chem Soc       Date:  2003-09-17       Impact factor: 15.419

Review 3.  Empirical antibacterial drug discovery--foundation in natural products.

Authors:  Sheo B Singh; John F Barrett
Journal:  Biochem Pharmacol       Date:  2006-01-19       Impact factor: 5.858

4.  Biochemistry. A new target for antibiotic development.

Authors:  Gerard D Wright
Journal:  Science       Date:  2007-03-09       Impact factor: 47.728

5.  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 6.  Assembly of the monomer unit of bacterial peptidoglycan.

Authors:  J van Heijenoort
Journal:  Cell Mol Life Sci       Date:  1998-04       Impact factor: 9.261

7.  Synthesis of P(1)-Citronellyl-P(2)-alpha-D-pyranosyl pyrophosphates as potential substrates for the E. coli undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG.

Authors:  P Cudic; D C Behenna; M K Yu; R G Kruger; L M Szewczuk; D G McCafferty
Journal:  Bioorg Med Chem Lett       Date:  2001-12-17       Impact factor: 2.823

8.  Synthesis of sub-micromolar inhibitors of MraY by exploring the region originally occupied by the diazepanone ring in the liposidomycin structure.

Authors:  C Dini; S Didier-Laurent; N Drochon; S Feteanu; J C Guillot; F Monti; E Uridat; J Zhang; J Aszodi
Journal:  Bioorg Med Chem Lett       Date:  2002-04-22       Impact factor: 2.823

Review 9.  Recent advances in antimicrobial nucleoside antibiotics targeting cell wall biosynthesis.

Authors:  Ken-ichi Kimura; Timothy D H Bugg
Journal:  Nat Prod Rep       Date:  2003-04       Impact factor: 13.423

10.  Capuramycin, a new nucleoside antibiotic. Taxonomy, fermentation, isolation and characterization.

Authors:  H Yamaguchi; S Sato; S Yoshida; K Takada; M Itoh; H Seto; N Otake
Journal:  J Antibiot (Tokyo)       Date:  1986-08       Impact factor: 2.649
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  17 in total

1.  Substrate Tolerance of Bacterial Glycosyltransferase MurG: Novel Fluorescence-Based Assays.

Authors:  Katsuhiko Mitachi; Hyun Gi Yun; Cody D Gillman; Karolina Skorupinska-Tudek; Ewa Swiezewska; William M Clemons; Michio Kurosu
Journal:  ACS Infect Dis       Date:  2019-12-11       Impact factor: 5.084

2.  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

3.  DPAGT1 Inhibitors of Capuramycin Analogues and Their Antimigratory Activities of Solid Tumors.

Authors:  Katsuhiko Mitachi; Rita G Kansal; Kirk E Hevener; Cody D Gillman; Syed M Hussain; Hyun Gi Yun; Gustavo A Miranda-Carboni; Evan S Glazer; William M Clemons; Michio Kurosu
Journal:  J Med Chem       Date:  2020-09-18       Impact factor: 7.446

4.  Fluorescence-based assay for polyprenyl phosphate-GlcNAc-1-phosphate transferase (WecA) and identification of novel antimycobacterial WecA inhibitors.

Authors:  Katsuhiko Mitachi; Shajila Siricilla; Dong Yang; Ying Kong; Karolina Skorupinska-Tudek; Ewa Swiezewska; Scott G Franzblau; Michio Kurosu
Journal:  Anal Biochem       Date:  2016-08-13       Impact factor: 3.365

5.  Synthesis of ureidomuraymycidine derivatives for structure-activity relationship studies of muraymycins.

Authors:  Bilal A Aleiwi; Christopher M Schneider; Michio Kurosu
Journal:  J Org Chem       Date:  2012-04-06       Impact factor: 4.354

6.  A reliable Pd-mediated hydrogenolytic deprotection of BOM group of uridine ureido nitrogen.

Authors:  Bilal A Aleiwi; Michio Kurosu
Journal:  Tetrahedron Lett       Date:  2012-05-12       Impact factor: 2.415

7.  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

8.  Chemoenzymatic syntheses of water-soluble lipid I fluorescent probes.

Authors:  Katsuhiko Mitachi; Shajila Siricilla; Lada Klaic; William M Clemons; Michio Kurosu
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

9.  Biosynthesis of a water-soluble lipid I analogue and a convenient assay for translocase I.

Authors:  Shajila Siricilla; Katsuhiko Mitachi; Karolina Skorupinska-Tudek; Ewa Swiezewska; Michio Kurosu
Journal:  Anal Biochem       Date:  2014-06-02       Impact factor: 3.365

10.  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
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