Archive for the ‘Uncategorized’ Category

Presenting two outlooks on Heparin synthesis

Natural Product Reports recently published two Highlight articles looking at Heparin, in contrasting but complementary approaches.

We thought you would like to have them side-by-side!

Pierre-Alexandre Driguez et al. present the total synthesis of Idra(biota)parinux, a fully synthetic analog of heparin, that has been designed and synthesized at Sanofi. Their Highlight also looks at chemical optimization performed in order to acheive the scale-up of batches, mandatory for clinical development. Jian Liu and Robert Linhardt’s article focuses on heparin syntheses that rely principally on enzymatic methods.

We hope you enjoy these articles. Let us kow what you think by leaving a comment below. Also, do keep an eye for a small web collection of articles on Carbohydrates, coming soon…

Synthetic oligosaccharides as active pharmaceutical ingredients: Lessons learned from the full synthesis of one heparin derivative on a large scale
Pierre-Alexandre Driguez, Pierre Potier and Patrick Trouilleux
Nat. Prod. Rep., 2014, 31, 980-989
DOI: 10.1039/C4NP00012A, Highlight

Chemoenzymatic synthesis of heparan sulfate and heparin
Jian Liu and Robert J. Linhardt
Nat. Prod. Rep., 2014,31, 1676-1685
DOI: 10.1039/C4NP00076E, Highlight

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Natural Products in Organic & Biomolecular Chemistry – our latest selection

Organic & Biomolecular Chemistry, our sister journal, publishes many articles that cover a variety of natural product chemistry.

We try to keep you updated here, although your best bet is for you to sign up to OBC’s e-alert (free service), and receive the tables of content directly in your inbox every time an issue is published.

Hand-picked for you from the latest issues are:

Methylthiodeoxynivalenol (MTD): insight into the chemistry, structure and toxicity of thia-Michael adducts of trichothecenes
Philipp Fruhmann, Theresa Weigl-Pollack, Hannes Mikula, Gerlinde Wiesenberger, Gerhard Adam, Elisabeth Varga, Franz Berthiller, Rudolf Krska, Christian Hametner and Johannes Fröhlich
Org. Biomol. Chem., 2014,12, 5144-5150
DOI: 10.1039/C4OB00458B

An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester): analogues, biological activities, and comparison with oleanolic acid derivatives
Liangfeng Fu, Qi-Xian Lin, Karen T. Liby, Michael B. Sporn and Gordon W. Gribble
Org. Biomol. Chem., 2014,12, 5192-5200
DOI: 10.1039/C4OB00679H

Marine natural products-inspired phenylmethylene hydantoins with potent in vitro and in vivo antitumor activities via suppression of Brk and FAK signaling
Asmaa A. Sallam, Mohamed M. Mohyeldin, Ahmed I. Foudah, Mohamed R. Akl, Sami Nazzal, Sharon A. Meyer, Yong-Yu Liu and Khalid A. El Sayed
Org. Biomol. Chem., 2014,12, 5295-5303
DOI: 10.1039/C4OB00553H

Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B
Jeffrey Buter, Renée Moezelaar and Adriaan J. Minnaard
Org. Biomol. Chem., 2014,12, 5883-5890
DOI: 10.1039/C4OB01085J

Synthesis and evaluation of the anticancer activity of albiziabioside A and its analogues as apoptosis inducers against human melanoma cells
Gaofei Wei, Shuai Wang, Shanshan Cui, Jia Guo, Yongxiang Liu, Yang Liu and Maosheng Cheng
Org. Biomol. Chem., 2014,12, 5928-5935
DOI: 10.1039/C4OB00874J

An unusual mulinane diterpenoid from the Chilean plant Azorella trifurcata (Gaertn) Pers
Carlos Areche, Beatriz Sepulveda, Aurelio San Martin, Olimpo Garcia-Beltrán, Mario Simirgiotis and Alvaro Cañete
Org. Biomol. Chem., 2014,12, 6406-6413
DOI: 10.1039/C4OB00966E

Total synthesis of the cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids derived from 2-hydroxy-6-methylcarbazole
Cemena Gassner, Ronny Hesse, Arndt W. Schmidt and Hans-Joachim Knölker
Org. Biomol. Chem., 2014,12, 6490-6499
DOI: 10.1039/C4OB01151A

We hope you enjoy this selection! Let us know what you think…
… and why not submit your latest natural product research to OBC today?

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Q2 Top 10 for Natural Product Reports

Please take a look at the top 10 most accessed Natural Product Reports articles for the second quarter of 2013:

Natural product isolation – how to get from biological material to pure compounds  
Franz Bucar, Abraham Wube and Martin Schmid  
Nat. Prod. Rep., 2013, 30, 525-545  
DOI: 10.1039/C3NP20106F 

Marine natural products  
John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro and Michèle R. Prinsep   
Nat. Prod. Rep., 2013, 30, 237-323  
DOI: 10.1039/C2NP20112G 

Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature  
Wilfred A. van der Donk, et al.
Nat. Prod. Rep., 2013, 30, 108-160    
DOI: 10.1039/C2NP20085F

Marine natural products: synthetic aspects 
Jonathan C. Morris   
Nat. Prod. Rep., 2013, 30, 783-805  
DOI: 10.1039/C3NP20116C 

Hot off the press  
Robert A. Hill and Andrew Sutherland 
Nat. Prod. Rep., 2013, 30, 760-764  
DOI: 10.1039/C3NP90015K  

The antibody-drug conjugate: an enabling modality for natural product-based cancer therapeutics  
Hans-Peter Gerber, Frank E. Koehn and Robert T. Abraham   
Nat. Prod. Rep., 2013, 30, 625-639  
DOI: 10.1039/C3NP20113A 

The enzymes of β-lactam biosynthesis 
Refaat B. Hamed, J. Ruben Gomez-Castellanos, Luc Henry, Christian Ducho, Michael A. McDonough and Christopher J. Schofield 
Nat. Prod. Rep., 2013, 30, 21-107  
DOI: 10.1039/C2NP20065A 

Simple indole alkaloids and those with a non-rearranged monoterpenoid unit  
Minoru Ishikura, Takumi Abe, Tominari Choshi and Satoshi Hibino  
Nat. Prod. Rep., 2013, 30, 694-752  
DOI: 10.1039/C3NP20118J 

Using NMR to identify and characterize natural products  
Rosemary C. Breton and William F. Reynolds   
Nat. Prod. Rep., 2013, 30, 501-524  
DOI: 10.1039/C2NP20104F 

Perspectives on natural product epigenetic modulators in chemical biology and medicine  
Fanny L. Cherblanc, Robert W. M. Davidson, Paolo Di Fruscia, Nitipol Srimongkolpithak and Matthew J. Fuchter 
Nat. Prod. Rep., 2013, 30, 605-624  
DOI: 10.1039/C3NP20097C 

We very much welcome your thoughts and comments about this blog below:

Fancy submitting an article to Natural Product Reports? Then why not submit to us today or alternatively email us your suggestions.

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Thiopeptide antibiotics, alpha-haloaldehydes, marine natural products and anticancer steroids – Your NPR issue 2


Welcome to NPR Issue 2, 2013

Issue 2s, home to the much awaited Marine Natural Products review by John Blunt et al., and much more.

Featuring on the front cover is the work of Jorge A. R. Salvador, M. Luisa Sá e Melo and colleagues at University of Coimbra and Universidade da Beira Interior (Portugal), illustrating their review detailing the anticancer activity of steroids.




In this issue:

Hot off the press
Robert A. Hill and Andrew Sutherland
DOI: 10.1039/C2NP90051C

A personal selection of 33 recent papers is presented covering various aspects of current developments in bioorganic chemistry and novel natural products such as breitfussin A from the Arctic hydrozoan Thuiaria breitfussi.

Biosynthesis of thiopeptide antibiotics and their pathway engineering
Qi Zhang and Wen Liu
DOI: 10.1039/C2NP20107K

A Highlight including advances during 2009–2012 in understanding the generality and specificity of thiopeptide biosynthesis, and on this basis, in expanding the structural diversity by pathway engineering.

 α-Haloaldehydes: versatile building blocks for natural product synthesis
Robert Britton and Baldip Kang
DOI: 10.1039/C2NP20108A

This Highlight summarizes the organocatalytic processes available for the enantioselective preparation of α-haloaldehydes and their stereoselective conversion into natural products.

Marine natural products
John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro and Michèle R. Prinsep
DOI: 10.1039/C2NP20112G

The much awaited Marine Natural Products review article! Included is an example of the development of genome mining for the discovery of new compounds from marine microbes leading to the finding of salinosporamide K from Salinispora pacifica.

Missed the previous ones? Catch up with the past 5 years of this series:
Marine Natural Products – 2012
Marine Natural Products – 2011
Marine Natural Products – 2010
Marine Natural Products – 2009
Marine Natural Products – 2008

Anticancer steroids: linking natural and semi-synthetic compounds
Jorge A. R. Salvador, João F. S. Carvalho, Marco A. C. Neves, Samuel M. Silvestre, Alcino J. Leitão, M. Manuel C. Silva and M. Luisa Sá e Melo
DOI: 10.1039/C2NP20082A

Steroids, a widespread class of natural compounds, have shown great therapeutic value for a broad array of pathologies. This overview is focused on their anticancer activity, which is very representative of a rich structural diversity and ability to interact with various biological targets and pathways.

Want to see your work in NPR?

Reviews, Highlights and Viewpoints in NPR are generally solicited by members of the editorial board; however we are happy to consider submission enquiries from authors. If you are interested in writing an article for NPR please contact the editorial office with a brief synopsis.

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Organic natural guanidines on the cover of NPR Issue 12, 2012

Welcome to NPR Issue 12, 2012

This month sees the work of Roberto Berlinck et al. on the cover, with a review showcasing naturally occurring guanidine compounds. Spanning natural guanidines from terrestrial, marine and freshwater microorganisms, marine invertebrates, sponges, or higher plants, the article highlights the newly isolated compounds along with their synthesis and biological properties.

The chemistry and biology of organic guanidine derivatives
Roberto G. S. Berlinck, Amaro E. Trindade-Silva and Mario F. C. Santos

This is the latest review on the topic, however this area is updated regularly. Why not also read some of the previous editions of this review, covering the time periods 2005/07, 2008/09.

Issue 12 also features the latest Hot of the Press, and reviews covering:

The impact of the United Nations Convention on Biological Diversity on natural products research
Gordon M. Cragg, Flora Katz, David J. Newman and Joshua Rosenthal
DOI: 10.1039/C2NP20091K

Investigations of the marine flora and fauna of the Fiji Islands
Klaus-Dieter Feussner, Kavita Ragini, Rohitesh Kumar, Katy M. Soapi, William G. Aalbersberg, Mary Kay Harper, Brad Carte and Chris M. Ireland
DOI: 10.1039/C2NP20055D

Ursane-type pentacyclic triterpenoids as useful platforms to discover anticancer drugs
Jorge A. R. Salvador, Vânia M. Moreira, Bruno M. F. Gonçalves, Ana S. Leal and Yongkui Jing
DOI: 10.1039/C2NP20060K

We hope you enjoy the issue!

And why not publish with us too? If you are interested in writing an article for NPR, please contact us at the editorial office.

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Top ten most accessed articles in July 2012

This month sees the following articles in Natural Product Reports that are in the top ten most accessed:

The generation of “unNatural” products: Synthetic biology meets synthetic chemistry  
Rebecca J. M. Goss, Sreejith Shankar and Antoine Abou Fayad  
Nat. Prod. Rep., 2012, 29, 870-889
DOI: 10.1039/C2NP00001F

Hot off the Press 
Robert A. Hill and Andrew Sutherland  
Nat. Prod. Rep., 2012, 29, 829-833
DOI: 10.1039/C2NP90024F 

Strained cyclophane natural products: Macrocyclization at its limits 
Tanja Gulder and Phil S. Baran  
Nat. Prod. Rep., 2012, 29, 899-934
DOI: 10.1039/C2NP20034A

Plants as sources of new antimicrobials and resistance-modifying agents  
Ana Cristina Abreu, Andrew J. McBain and Manuel Simões  
Nat. Prod. Rep., 2012, 29, 1007-1021
DOI: 10.1039/C2NP20035J

Marine natural products  
John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro and Michèle R. Prinsep  
Nat. Prod. Rep., 2012, 29, 144-222
DOI: 10.1039/C2NP00090C 

Natural products from Cephalotaxus sp.: chemical diversity and synthetic aspects  
Hajer Abdelkafi and Bastien Nay  
Nat. Prod. Rep., 2012, 29, 845-869
DOI: 10.1039/C2NP20037F 

Isolation, biological activity, synthesis, and medicinal chemistry of the pederin/mycalamide family of natural products  
R. Adam Mosey and Paul E. Floreancig  
Nat. Prod. Rep., 2012, 29, 980-995
DOI: 10.1039/C2NP20052J 

Diterpenoids of terrestrial origin  
James R. Hanson  
Nat. Prod. Rep., 2012, 29, 890-898
DOI: 10.1039/C2NP20051A 

The nonribosomal synthesis of diketopiperazines in tRNA-dependent cyclodipeptide synthase pathways  
Pascal Belin, Mireille Moutiez, Sylvie Lautru, Jérôme Seguin, Jean-Luc Pernodet and Muriel Gondry
Nat. Prod. Rep., 2012, 29, 961-979
DOI: 10.1039/C2NP20010D 

Diversity of P450 enzymes in the biosynthesis of natural products  
Larissa M. Podust and David H. Sherman  
Nat. Prod. Rep., 2012, 29, 1251-1266
DOI: 10.1039/C2NP20020A

Why not take a look at the articles today and blog your thoughts and comments below.

Fancy submitting an article to Natural Product Reports? Then why not submit to us today or alternatively email us your suggestions.

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Our selection of Natural Products in OBC and MedChemComm

Organic & Biomolecular Chemistry, our sister journal, publishes many articles that cover a variety of natural product chemistry.

We try to keep you updated here, although your best bet is for you to sign up to OBC’s e-alert (free service), and receive the tables of content directly in your inbox every time an issue is published.

The latest natural products’ related articles have been collated here:

Chemoenzymatic synthesis, structural study and biological activity of novel indolizidine and quinolizidine iminocyclitols
Livia Gómez, Xavier Garrabou, Jesús Joglar, Jordi Bujons, Teodor Parella, Cristina Vilaplana, Pere Joan Cardona and Pere Clapés

Synthesis of the O-linked hexasaccharide containing β-D-Galf-(1→2)-β-D-Galf in Trypanosoma cruzi mucins
Gustavo A. Kashiwagi, Verónica M. Mendoza, Rosa M. de Lederkremer and Carola Gallo-Rodriguez

Modification in the side chain of solomonsterol A: discovery of cholestan disulfate as a potent pregnane-X-receptor agonist
Valentina Sepe, Raffaella Ummarino, Maria Valeria D’Auria, Gianluigi Lauro, Giuseppe Bifulco, Claudio D’Amore, Barbara Renga, Stefano Fiorucci and Angela Zampella

Synthesis and biological activity of simplified belactosin C analogues
Armin de Meijere, Vadim S. Korotkov, Alexander V. Lygin, Oleg V. Larionov, Viktor V. Sokolov, Tine Graef and Mazen Es-Sayed

Alkadienyl and alkenyl itaconic acids (ceriporic acids G and H) from the selective white-rot fungus Ceriporiopsis subvermispora: a new class of metabolites initiating ligninolytic lipid peroxidation
Hiroshi Nishimura, Midori Sasaki, Hirofumi Seike, Masaharu Nakamura and Takashi Watanabe

Asymmetric synthesis of (+)-vertine and (+)-lythrine
Laëtitia Chausset-Boissarie, Roman Àrvai, Graham R. Cumming, Laure Guénée and E. Peter Kündig

Total synthesis and structural elucidation of ent-micropyrone and (+)-ascosalipyrone
Claire Gregg and Michael V. Perkins

Have you read the Natural Products themed issue from MedChemComm? Guest edited by Professor Christopher Walsh and Dr Sylvie Garneau-Tsdodikova, the issue contains some of the newest discoveries in the field, along with 9 review articles that will lead the reader through exciting natural products research. Let us know what you think!

    

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Top ten most accessed articles in February

This month sees the following articles in Natural Product Reports that are in the top ten most accessed:

Marine natural products
John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro and Michèle R. Prinsep
Nat. Prod. Rep., 2012, 29, 144-222
DOI: 10.1039/C2NP00090C

Natural products as kinase inhibitors
Jing Liu, Yi Hu, David L. Waller, Junfeng Wang and Qingsong Liu
Nat. Prod. Rep., 2012, 29, 392-403
DOI: 10.1039/C2NP00097K

Electrophilic and nucleophilic enzymatic cascade reactions in biosynthesis
Barbara T. Ueberbacher, Mélanie Hall and Kurt Faber
Nat. Prod. Rep., 2012, 29, 337-350
DOI: 10.1039/C2NP00078D

Advances in Aspergillus secondary metabolite research in the post-genomic era
James F. Sanchez, Amber D. Somoza, Nancy P. Keller and Clay C. C. Wang
Nat. Prod. Rep., 2012, 29, 351-371
DOI: 10.1039/C2NP00084A

Hot off the press
Robert A. Hill and Andrew Sutherland
Nat. Prod. Rep., 2012, 29, 129-133
DOI: 10.1039/C1NP90052H

The chemical ecology of cyanobacteria
Pedro N. Leão, Niclas Engene, Agostinho Antunes, William H. Gerwick and Vitor Vasconcelos
Nat. Prod. Rep., 2012, 29, 372-391
DOI: 10.1039/C2NP00075J

Influenza neuraminidase: A druggable target for natural products
Ulrike Grienke, Michaela Schmidtke, Susanne von Grafenstein, Johannes Kirchmair, Klaus R. Liedl and Judith M. Rollinger
Nat. Prod. Rep., 2012, 29, 11-36
DOI: 10.1039/C1NP00053E

Key achievements in the total synthesis of vibsane-type diterpenoids
Jeffrey Y. W. Mak and Craig M. Williams
Nat. Prod. Rep., 2012, 29, 440-448
DOI: 10.1039/C2NP00067A

Triptolide: structural modifications, structure–activity relationships, bioactivities, clinical development and mechanisms
Zhao-Li Zhou, Ya-Xi Yang, Jian Ding, Yuan-Chao Li and Ze-Hong Miao
Nat. Prod. Rep., 2012, 29, 457-475
DOI: 10.1039/C2NP00088A

The taxonomy, biology and chemistry of the fungal Pestalotiopsis genus
Xiao-Long Yang, Jing-Ze Zhang and Du-Qiang Luo
Nat. Prod. Rep., 2012, Advance Article
DOI: 10.1039/C2NP00073C

Why not take a look at the articles today and blog your thoughts and comments below.

Fancy submitting an article to Natural Product Reports? Then why not submit to us today or alternatively email us your suggestions.

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Enzymatic cascade reactions in biosynthesis on the cover of NPR issue 3, 2012

Welcome to NPR issue 3, 2012!

This month’s cover features the work of Kurt Faber et al. at the University of Graz, Austria, with a review on the enzyme-initiated cascade reactions for the ring formation of cyclic terpenoids and polyethers. The authors provide a mechanistic analysis of enzymatic cascade reactions leading to biomimetic strategies for natural product synthesis. 

Also in the issue, read Clay C. C. Wang‘s review article on the  impact of whole genome sequencing on Aspergillus secondary metabolite research:

Pedro N. Leão and coworkers provide insights into the chemical ecology of cyanobacteria, highlighting both evolutionary and chemotaxonomical studies:

Qingsong Liu et al. review the history of several classes of natural products as kinase inhibitors, analyzing their structural binding information and highlighting their therapeutic development potential:

Why not also read on the didemnin family of marine depsipeptides in this review article by Madeleine M. Joullié et al..  The authors highlight the long-standing study of didemnins and its critical application towards the understanding of the molecular mechanism of action of tamandarins and their potential use as therapeutic agents:

 We hope that you enjoy this issue!

View the issue

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Natural Products in OBC

Organic & Biomolecular Chemistry, our sister journal, publishes many articles that cover natural product chemistry.

We will try to keep you updated, although the safest bet is for you to sign up to OBC’s e-alert (free service) and receive the table of content directly in your inbox every time an issue is published.

The latest natural products’ related articles from OBC issue 9 have been collated here:

Studies of the H–D exchange mechanism of malonganenone B
Peter G. K. Clark, Matthias Lein and Robert A. Keyzers

Unexpected enzyme-catalyzed regioselective acylation of flavonoid aglycones and rapid product screening
Eleni Kyriakou, Alexandra Primikyri, Pantelis Charisiadis, Maria Katsoura, Ioannis P. Gerothanassis, Haralambos Stamatis and Andreas G. Tzakos

Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: confirmation of the relative stereochemistry
Norazah B. Basar, Hao Liu, Devendra Negi, Hasnah M. Sirat, Gareth A. Morris and Eric J. Thomas

An iterative Shimizu non-aldol approach for the stereoselective synthesis of C13-C22 fragment of callystatin A
Sandip A. Pujari and Krishna P. Kaliappan

Organocatalytic stereoselective synthesis of passifloricin A
Pradeep Kumar, Menaka Pandey, Priti Gupta and Dilip D. Dhavale

Stereocontrolled asymmetric synthesis of syn-E-1,4-diol-2-enes using allyl boronates and its application in the total synthesis of solandelactone F
Anna Robinson and Varinder K. Aggarwal

Enantioselective synthesis of the carbocyclic nucleoside (−)-abacavir
Grant A. Boyle, Christopher D. Edlin, Yongfeng Li, Dennis C. Liotta, Garreth L. Morgans and Chitalu C. Musonda


 

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