Literature DB >> 27723359

Total Synthesis and Biological Evaluation of Apratoxin E and Its C30 Epimer: Configurational Reassignment of the Natural Product.

Ping Wu1, Weijing Cai2,3, Qi-Yin Chen2,3, Senhan Xu1, Ruwen Yin1, Yingxia Li1, Wei Zhang1, Hendrik Luesch2,3.   

Abstract

Apratoxin E provided the inspiration for the design of apratoxin A/E hybrids under preclinical development. Through total synthesis using two different strategies, it was determined that the originally proposed configuration of the thiazoline at C30 is opposite from that in apratoxin A, in contrast to previous assumptions on biosynthetic grounds. The epimer and true natural apratoxin E were synthesized, and the biological activities were evaluated.

Entities:  

Year:  2016        PMID： 27723359      PMCID： PMC5386831          DOI： 10.1021/acs.orglett.6b02780

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


  17 in total

1.  New apratoxins of marine cyanobacterial origin from Guam and Palau.

Authors:  Hendrik Luesch; Wesley Y Yoshida; Richard E Moore; Valerie J Paul
Journal:  Bioorg Med Chem       Date:  2002-06       Impact factor: 3.641

2.  A functional genomics approach to the mode of action of apratoxin A.

Authors:  Hendrik Luesch; Sumit K Chanda; R Marina Raya; Paul D DeJesus; Anthony P Orth; John R Walker; Juan Carlos Izpisúa Belmonte; Peter G Schultz
Journal:  Nat Chem Biol       Date:  2006-02-12       Impact factor: 15.040

3.  3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): a new coupling reagent with remarkable resistance to racemization.

Authors:  H Li; X Jiang; Y H Ye; C Fan; T Romoff; M Goodman
Journal:  Org Lett       Date:  1999-07-15       Impact factor: 6.005

4.  Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula.

Authors:  H Luesch; W Y Yoshida; R E Moore; V J Paul; T H Corbett
Journal:  J Am Chem Soc       Date:  2001-06-13       Impact factor: 15.419

5.  DEPBT as an efficient coupling reagent for amide bond formation with remarkable resistance to racemization.

Authors:  Yun-Hua Ye; Haitao Li; Xiaohui Jiang
Journal:  Biopolymers       Date:  2005       Impact factor: 2.505

6.  Total synthesis of apratoxin A.

Authors:  Jiehao Chen; Craig J Forsyth
Journal:  J Am Chem Soc       Date:  2003-07-23       Impact factor: 15.419

7.  Apratoxin a reversibly inhibits the secretory pathway by preventing cotranslational translocation.

Authors:  Yanxia Liu; Brian K Law; Hendrik Luesch
Journal:  Mol Pharmacol       Date:  2009-04-29       Impact factor: 4.436

8.  Apratoxin D, a potent cytotoxic cyclodepsipeptide from papua new guinea collections of the marine cyanobacteria Lyngbya majuscula and Lyngbya sordida.

Authors:  Marcelino Gutiérrez; Takashi L Suyama; Niclas Engene; Joshua S Wingerd; Teatulohi Matainaho; William H Gerwick
Journal:  J Nat Prod       Date:  2008-04-30       Impact factor: 4.050

9.  Total synthesis of the marine cyanobacterial cyclodepsipeptide apratoxin A.

Authors:  Jiehao Chen; Craig J Forsyth
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-01       Impact factor: 11.205

10.  Apratoxin E, a cytotoxic peptolide from a guamanian collection of the marine cyanobacterium Lyngbya bouillonii.

Authors:  Susan Matthew; Peter J Schupp; Hendrik Luesch
Journal:  J Nat Prod       Date:  2008-05-08       Impact factor: 4.050
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  6 in total

1.  Sec61 Inhibitor Apratoxin S4 Potently Inhibits SARS-CoV-2 and Exhibits Broad-Spectrum Antiviral Activity.

Authors:  Marie O Pohl; Laura Martin-Sancho; Ranjala Ratnayake; Kris M White; Laura Riva; Qi-Yin Chen; Gauthier Lieber; Idoia Busnadiego; Xin Yin; Samuel Lin; Yuan Pu; Lars Pache; Romel Rosales; Marion Déjosez; Yiren Qin; Paul D De Jesus; Anne Beall; Sunnie Yoh; Benjamin G Hale; Thomas P Zwaka; Naoko Matsunaga; Adolfo García-Sastre; Silke Stertz; Sumit K Chanda; Hendrik Luesch
Journal:  ACS Infect Dis       Date:  2022-06-29       Impact factor: 5.578

Review 2.  Natural products as modulators of eukaryotic protein secretion.

Authors:  Hendrik Luesch; Ville O Paavilainen
Journal:  Nat Prod Rep       Date:  2020-02-18       Impact factor: 13.423

3.  Apratoxin S10, a Dual Inhibitor of Angiogenesis and Cancer Cell Growth To Treat Highly Vascularized Tumors.

Authors:  Weijing Cai; Qi-Yin Chen; Long H Dang; Hendrik Luesch
Journal:  ACS Med Chem Lett       Date:  2017-09-18       Impact factor: 4.345

4.  Bifunctional Doscadenamides Activate Quorum Sensing in Gram-Negative Bacteria and Synergize with TRAIL to Induce Apoptosis in Cancer Cells.

Authors:  Xiao Liang; Qi-Yin Chen; Gustavo M Seabra; Susan Matthew; Jason C Kwan; Chenglong Li; Valerie J Paul; Hendrik Luesch
Journal:  J Nat Prod       Date:  2021-01-22       Impact factor: 4.050

Review 5.  Recent developments in the asymmetric Reformatsky-type reaction.

Authors:  Hélène Pellissier
Journal:  Beilstein J Org Chem       Date:  2018-02-02       Impact factor: 2.883

6.  Inhibition of cotranslational translocation by apratoxin S4: Effects on oncogenic receptor tyrosine kinases and the fate of transmembrane proteins produced in the cytoplasm.

Authors:  Weijing Cai; Ranjala Ratnayake; Mengxiong Wang; Qi-Yin Chen; Kevin P Raisch; Long H Dang; Brian K Law; Hendrik Luesch
Journal:  Curr Res Pharmacol Drug Discov       Date:  2021-09-08
  6 in total

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