Literature DB >> 30698984

Semisynthesis of an Anticancer DPAGT1 Inhibitor from a Muraymycin Biosynthetic Intermediate.

Katsuhiko Mitachi1, Shou M Kurosu1, Shakiba Eslamimehr1, Maddie R Lemieux1, Yoshimasa Ishizaki2, William M Clemons3, Michio Kurosu1.   

Abstract

We have explored a method to convert a muraymycin biosynthetic intermediate 3 to an anticancer drug lead 2 for in vivo and thorough preclinical studies. Cu(OAc)2 forms a stable complex with the amide 4 and prevents electrophilic reactions at the 2-((3-aminopropyl)amino)acetamide moiety. Under the present conditions, the desired 5″-primary amine was selectively protected with (Boc)2O to yield 6. The intermediate 6 was converted to 2 in two steps with 90% yield.

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Year:  2019        PMID： 30698984      PMCID： PMC6447083          DOI： 10.1021/acs.orglett.8b03716

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


  20 in total

1.  Coupling of stress in the ER to activation of JNK protein kinases by transmembrane protein kinase IRE1.

Authors:  F Urano; X Wang; A Bertolotti; Y Zhang; P Chung; H P Harding; D Ron
Journal:  Science       Date:  2000-01-28       Impact factor: 47.728

2.  Identification of the gene cluster involved in muraymycin biosynthesis from Streptomyces sp. NRRL 30471.

Authors:  Lin Cheng; Wenqing Chen; Lipeng Zhai; Dongmei Xu; Tingting Huang; Shuangjun Lin; Xiufen Zhou; Zixin Deng
Journal:  Mol Biosyst       Date:  2010-12-23

3.  Cytosine deaminase as a negative selection marker for gene disruption and replacement in the genus Streptomyces and other actinobacteria.

Authors:  Marie-Pierre Dubeau; Mariana Gabriela Ghinet; Pierre-Etienne Jacques; Nancy Clermont; Carole Beaulieu; Ryszard Brzezinski
Journal:  Appl Environ Microbiol       Date:  2008-12-19       Impact factor: 4.792

4.  XBP1 mRNA is induced by ATF6 and spliced by IRE1 in response to ER stress to produce a highly active transcription factor.

Authors:  H Yoshida; T Matsui; A Yamamoto; T Okada; K Mori
Journal:  Cell       Date:  2001-12-28       Impact factor: 41.582

5.  A new Oxyma derivative for nonracemizable amide-forming reactions in water.

Authors:  Qinghui Wang; Yong Wang; Michio Kurosu
Journal:  Org Lett       Date:  2012-06-14       Impact factor: 6.005

6.  Increased ER-mitochondrial coupling promotes mitochondrial respiration and bioenergetics during early phases of ER stress.

Authors:  Roberto Bravo; Jose Miguel Vicencio; Valentina Parra; Rodrigo Troncoso; Juan Pablo Munoz; Michael Bui; Clara Quiroga; Andrea E Rodriguez; Hugo E Verdejo; Jorge Ferreira; Myriam Iglewski; Mario Chiong; Thomas Simmen; Antonio Zorzano; Joseph A Hill; Beverly A Rothermel; Gyorgy Szabadkai; Sergio Lavandero
Journal:  J Cell Sci       Date:  2011-05-31       Impact factor: 5.285

7.  Muraymycins, novel peptidoglycan biosynthesis inhibitors: semisynthesis and SAR of their derivatives.

Authors:  Yang-I Lin; Zhong Li; Gerardo D Francisco; Leonard A McDonald; Rachel A Davis; Guy Singh; Youjun Yang; Tarek S Mansour
Journal:  Bioorg Med Chem Lett       Date:  2002-09-02       Impact factor: 2.823

8.  Regulation of the selenoprotein SelS by glucose deprivation and endoplasmic reticulum stress - SelS is a novel glucose-regulated protein.

Authors:  Yuan Gao; Helen C Feng; Ken Walder; Kristy Bolton; Terry Sunderland; Natalie Bishara; Melissa Quick; Lakshmi Kantham; Greg R Collier
Journal:  FEBS Lett       Date:  2004-04-09       Impact factor: 4.124

9.  Apoptosis induced by endoplasmic reticulum stress depends on activation of caspase-3 via caspase-12.

Authors:  Junichi Hitomi; Taiichi Katayama; Manabu Taniguchi; Akiko Honda; Kazunori Imaizumi; Masaya Tohyama
Journal:  Neurosci Lett       Date:  2004-03-04       Impact factor: 3.046

10.  Structures of the muraymycins, novel peptidoglycan biosynthesis inhibitors.

Authors:  Leonard A McDonald; Laurel R Barbieri; Guy T Carter; Eileen Lenoy; Jason Lotvin; Peter J Petersen; Marshall M Siegel; Guy Singh; R Thomas Williamson
Journal:  J Am Chem Soc       Date:  2002-09-04       Impact factor: 15.419
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  8 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.  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.  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.  Application of Mycobacterium smegmatis as a surrogate to evaluate drug leads against Mycobacterium tuberculosis.

Authors:  Nada Lelovic; Katsuhiko Mitachi; Junshu Yang; Maddie R Lemieux; Yinduo Ji; Michio Kurosu
Journal:  J Antibiot (Tokyo)       Date:  2020-05-29       Impact factor: 2.649

5.  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

6.  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

7.  Antibacterial Activity of Pharmaceutical-Grade Rose Bengal: An Application of a Synthetic Dye in Antibacterial Therapies.

Authors:  Michio Kurosu; Katsuhiko Mitachi; Junshu Yang; Edward V Pershing; Bruce D Horowitz; Eric A Wachter; John W Lacey; Yinduo Ji; Dominic J Rodrigues
Journal:  Molecules       Date:  2022-01-05       Impact factor: 4.411

8.  A five-mRNA signature associated with post-translational modifications can better predict recurrence and survival in cervical cancer.

Authors:  Mingyi Ju; Aoshuang Qi; Jia Bi; Lan Zhao; Longyang Jiang; Qiang Zhang; Qian Wei; Qiutong Guan; Xueping Li; Lin Wang; Minjie Wei; Lin Zhao
Journal:  J Cell Mol Med       Date:  2020-04-19       Impact factor: 5.310
  8 in total

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