Archive for June, 2017

Natural Products in OBC

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 signing up to OBC’s e-alert (free service) means you will receive the tables of content directly in your inbox every time an issue is published.

Hand-picked for you from the latest issues are:

Total synthesis of (+)-herboxidiene/GEX 1A
Alejandro Gómez-Palomino, Miquel Pellicena, Katrina Krämer, Pedro Romea, Fèlix Urpí, Gabriel Aullón and José M. Padrón
DOI: 10.1039/C7OB00072C, Paper


First asymmetric total synthesis of aspergillide D
Bighnanshu K. Jena, G. Sudhakar Reddy and Debendra K. Mohapatra
DOI: 10.1039/C6OB02435A, Paper


Torsional steering as friend and foe: development of a synthetic route to the briarane diterpenoid stereotetrad
Nicholas G. Moon and Andrew M. Harned  
DOI: 10.1039/C7OB00124J, Paper


Computational studies on the cyclization of squalene to the steroids and hopenes
B. Andes Hess
DOI: 10.1039/C7OB00222J, Review Article


Isoafricanol synthase from Streptomyces malaysiensis
Patrick Rabe, Markiyan Samborskyy, Peter F. Leadlay and Jeroen S. Dickschat  
DOI: 10.1039/C7OB00234C, Communication


An efficient Ugi-3CR/aza Diels–Alder/Pomeranz–Fritsch protocol towards novel aza-analogues of (±)-nuevamine, (±)-lennoxamine and magallanesine: a diversity oriented synthesis approach
Óscar Vázquez-Vera, Jorge S. Sánchez-Badillo, Alejandro Islas-Jácome, Manuel A. Rentería-Gómez, Shrikant G. Pharande, Carlos J. Cortes-García, Mónica A. Rincón-Guevara, Ilich A. Ibarra, Rocío Gámez-Montaño and Eduardo González-Zamora  
DOI: 10.1039/C6OB02572B, Paper


Intramolecular macrolactonization, photophysical and biological studies of new class of polycyclic pyrrole derivatives
Suresh Kumar Mondal, Arabinda Mandal, Susanta Kumar Manna, Sk Asraf Ali, Maidul Hossain, Vangala Venugopal, Avijit Jana and Shubhankar Samanta  
DOI: 110.1039/C7OB00160F, Paper


Isolation and structure elucidation of natural products of three soft corals and a sponge from the coast of Madagascar
Marie Pascaline Rahelivao, Tilo Lübken, Margit Gruner, Olga Kataeva, Rahanira Ralambondrahety, Hanta Andriamanantoanina, Marek P. Checinski, Ingmar Bauer and Hans-Joachim Knölker  
DOI: 10.1039/C7OB00191F, Paper


Total synthesis of phenylpropanoid glycoside osmanthuside-B6 facilitated by double isomerisation of glucose–rhamnose orthoesters
Duc Thinh Khong and Zaher M. A. Judeh  
DOI: 10.1039/C7OB00198C, Paper


Biosynthetic 4,6-dehydratase gene deletion: isolation of a glucosylated jadomycin natural product provides insight into the substrate specificity of glycosyltransferase JadS
S. M. Forget, Jungwook Na, N. E. McCormick and D. L. Jakeman
DOI: 10.1039/C7OB00259A, Communication


Syntheses of C17–C27 fragments of 20-deoxybryostatins for assembly using Julia and metathesis reactions
Matthew Ball, Thomas Gregson, Hiroki Omori and Eric J. Thomas  
DOI: 10.1039/C7OB00076F, Paper


Some limitations of an approach to the assembly of bryostatins by ring-closing metathesis
Raphaël Dumeunier, Thomas Gregson, Somhairle MacCormick, Hiroki Omori and Eric J. Thomas  
DOI: 10.1039/C7OB00079K, Paper


Stereochemical investigations of the Tetrahymena cyclase, a model system for euphane/tirucallane biosynthesis
José-Luis Giner and Ju Feng  
DOI: 10.1039/C7OB00296C, Paper


 

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18th International Symposium on the Biology of Actinomycetes (ISBA18)

HeeJu Nah receiving her poster prize certificate

We were pleased to present a prize at the 18th International Symposium on the Biology of Actinomycetes to HeeJu Nah (Department of Biological Engineering, Inha University, Korea) for her poster on:

“Precise Cloning and Heterologous Expression of Natural Product Biosynthetic Gene Cluster Using Streptomyces Artificial Chromosome System.”

The symposium took place in Jeju, Korea on 23 – 27th May 2017.

The International Symposium on the Biology of Actinomycetes is the premier conference in the field, covering all aspects from basic biology through to the applications of the metabolites these fascinating bacteria produce. The conference attracted 582 delegates, with speakers and sponsors from over 30 countries around the world, bringing together both well-established and promising scientists who were keen to discuss Actinobacteria. Actinomycetes are prolific producers of antibiotics and other bioactive natural products, including many compounds used in medicine and agriculture, such as erythromycin, rifampicin, amphotericin, doxorubicin, avermectin and spinosyn.

NPR Board members, Professor Greg Challis, Professor Yeo Joon Yoon and Dr Rebecca Goss were all in attendance at the meeting. Here is what they had to say about the meeting; The 18th meeting in the series featured many exciting talks on the discovery, biosynthesis and bioengineering of actinomycete natural products of direct relevance to readers of NPR. The conference programme included 13 symposia, 3 workshop sessions, 9 plenary lectures and a special lecture by 2015 Nobel Laureate Professor Satoshi Ōmura. Professor Ōmura overviewed the > 400 natural products that his group had isolated, with >20 being of clinical significance. This was particularly impressive, especially when one considers the NMR capability in the early days of his research. This was inspirational to young scientists and students in the field of natural products.

Excitingly, the symposium highlighted the huge acceleration in the field of natural product discovery, enabled by the availability of sequenced actinomycetes genomes, the development of tools for the identification of biosynthetic gene clusters (BGCs) encoded within the genomes, prediction of their products, and the development of technologies enabling access to the products of these previously silent BGCs.

There was a strong strand of fundamental, developmental actinomycetes biology that ran throughout and underpinned the symposium. It is critical to the international community that research into this area remains vibrant and is well supported. Understanding the development and stability of these important antibiotic producers is crucial to optimising and sustaining them for the fermentative production of natural products.

Why not take a look at some related NPR articles here:

Antibiotics from Gram-negative bacteria: a comprehensive overview and selected biosynthetic highlights
J. Masschelein, M. Jenner and G. L. Challis
DOI: 10.1039/C7NP00010C

Opportunities for natural products in 21st century antibiotic discovery
Gerard D. Wright
DOI: 10.1039/C7NP00019G

Symbiosis-inspired approaches to antibiotic discovery
Navid Adnani, Scott R. Rajski and Tim S. Bugni
DOI: 10.1039/C7NP00009J

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Katherine S. Ryan receives NPR Lectureship at 9th US-Japan Seminar on Biosynthesis of Natural Products

Professor Katherine S. Ryan winner of the 2017 Natural Product Reports Emerging Investigator Lectureship delivered her lecture on “A PLP-dependent oxidase in the biosynthesis of indolmycin” at the recent 9th US-Japan Seminar on the Biosynthesis of Natural Products at the UCLA Lake Arrowhead Conference Center in California.  

The Natural Product Reports Emerging Investigator Lectureship is an annual event which is held at an international meeting, the recipient being a researcher who has made a significant contribution to any natural products-related research in their early independent career.

Katherine was selected to receive the lectureship for her significant contributions to understanding the unusual biosynthetic chemistry of antibiotics such as indolmycin and for using modern synthetic biology techniques to rationally generate new bisindole chemistry.

Find out more about Katherine and her research on Katherine’s webpage.

Nominations will be open for the 2018 Natural Product Reports Emerging Investigator Lectureship later this year. This will be announced on our blog so check back here regularly.

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Natural Products in OBC

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 signing up to OBC’s e-alert (free service) means you will receive the tables of content directly in your inbox every time an issue is published.

Hand-picked for you from the latest issues are:

Bioinspired total syntheses of terpenoids
Cedric L. Hugelshofer and Thomas Magauer
DOI: 10.1039/C6OB02488B, Perspective

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Total synthesis and confirmation of the revised structures of jiangrines A, C and D
Zhijiang Zhang and Bo Liu
DOI: 10.1039/C6OB02379G, Paper

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Fluorometabolite biosynthesis: isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus
Axel Bartholomé, Jeffrey E. Janso, Usa Reilly and David O’Hagan
DOI: 10.1039/C6OB02291J, Communication

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Enantiospecific total syntheses of meroterpenoids (−)-F1839-I and (−)-corallidictyals B and D
Dattatraya H. Dethe, Balu D. Dherange, Saghir Ali and Mahesh M. Parsutkar
DOI: 10.1039/C6OB02322C, Communication

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Second-generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions
Ichiro Hayakawa, Keita Saito, Sachiko Matsumoto, Shinichi Kobayashi, Ayaka Taniguchi, Kenichi Kobayashi, Yusuke Fujii, Takahiro Kaneko and Hideo Kigoshi
DOI: 10.1039/C6OB02241C, Paper

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The first total synthesis of the marine acetylenic alcohol, lembehyne B – a selective inducer of early apoptosis in leukemia cancer cells
Lilya U. Dzhemileva, Vladimir A. D’yakonov, Aleksey A. Makarov, Evgeny N. Andreev, Milyausha M. Yunusbaeva and Usein M. Dzhemilev  
DOI: 10.1039/C6OB02346K, Paper

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An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (−)-hapalosin
Chang-Mei Si, Lu-Ping Shao, Zhuo-Ya Mao, Wen Zhou and Bang-Guo Wei  
DOI: 10.1039/C6OB02523D, Paper

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A protecting-group-free synthesis of (+)-nephrosteranic, (+)-protolichesterinic, (+)-nephrosterinic, (+)-phaseolinic, (+)-rocellaric acids and (+)-methylenolactocin
Jothi L. Nallasivam and Rodney A. Fernandes
DOI: 10.1039/C6OB02398C, Paper

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Stepwise cyclopropanation on the polycyclopropanated polyketide formation in jawsamycin biosynthesis
Tomoshige Hiratsuka, Hideaki Suzuki, Atsushi Minami and Hideaki Oikawa
DOI: 10.1039/C6OB02675C, Communication

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A novel withanolide with an unprecedented carbon skeleton from Physalis angulata
Cheng-Peng Sun, Andrei G. Kutateladze, Feng Zhao, Li-Xia Chen and Feng Qiu  
DOI: 10.1039/C6OB02656G, Communication

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Total synthesis and biological activity of dolastatin 16
Loida O. Casalme, Arisa Yamauchi, Akinori Sato, Julie G. Petitbois, Yasuyuki Nogata, Erina Yoshimura, Tatsufumi Okino, Taiki Umezawa and Fuyuhiko Matsuda  
DOI: 10.1039/C6OB02657E, Paper

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New compounds from a hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4
Chengqian Pan, Yutong Shi, Xuegang Chen, Chen-Tung Arthur Chen, Xinyi Tao and Bin Wu  
DOI: 10.1039/C6OB02374F, Paper

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Chemoenzymatic synthesis of unmodified heparin oligosaccharides: cleavage of p-nitrophenyl glucuronide by alkaline and Smith degradation
Xing Zhang, Yongmei Xu, Po-Hung Hsieh, Jian Liu, Lei Lin, Eric P. Schmidt and Robert J. Linhardt  
DOI: 10.1039/C6OB02603F, Paper

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Isoafricanol synthase from Streptomyces malaysiensis
Patrick Rabe, Markiyan Samborskyy, Peter F. Leadlay and Jeroen S. Dickschat  
DOI: 10.1039/C7OB00234C, Communication

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An efficient Ugi-3CR/aza Diels–Alder/Pomeranz–Fritsch protocol towards novel aza-analogues of (±)-nuevamine, (±)-lennoxamine and magallanesine: a diversity oriented synthesis approach
Óscar Vázquez-Vera, Jorge S. Sánchez-Badillo, Alejandro Islas-Jácome, Manuel A. Rentería-Gómez, Shrikant G. Pharande, Carlos J. Cortes-García, Mónica A. Rincón-Guevara, Ilich A. Ibarra, Rocío Gámez-Montaño and Eduardo González-Zamora  
DOI: 10.1039/C6OB02572B, Paper

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Intramolecular macrolactonization, photophysical and biological studies of new class of polycyclic pyrrole derivatives
Suresh Kumar Mondal, Arabinda Mandal, Susanta Kumar Manna, Sk Asraf Ali, Maidul Hossain, Vangala Venugopal, Avijit Jana and Shubhankar Samanta  
DOI: 10.1039/C7OB00160F, Paper

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Natural Products in OBC

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 signing up to OBC’s e-alert (free service) means you will receive the tables of content directly in your inbox every time an issue is published.

Hand-picked for you from the latest issues are:

 

Gold catalysis: synthesis of spiro, bridged, and fused ketal natural products
Rachelle Quach, Daniel P. Furkert and Margaret A. Brimble  
DOI: 10.1039/C7OB00496F, Review Article

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Application of the aza-Diels–Alder reaction in the synthesis of natural products
Min-Hui Cao, Nicholas J. Green and Sheng-Zhen Xu  
DOI: 10.1039/C6OB02761J, Review Article

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ipso-Cyclization: an emerging tool for multifunctional spirocyclohexadienones
Chada Raji Reddy, Santosh Kumar Prajapti, Kamalkishor Warudikar, Ravi Ranjan and Billa Bhargava Rao  
DOI: 10.1039/C7OB00405B, Review Article

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cis or trans with class II diterpene cyclases
Meirong Jia and Reuben J. Peters  
DOI: 10.1039/C7OB00510E, Communication

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Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene
Mikail E. Abbasov, Brandi M. Hudson, Weixu Kong, Dean J. Tantillo and Daniel Romo  
DOI: 10.1039/C6OB02738E, Communication

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Synthesis, SAR and biological studies of sugar amino acid-based almiramide analogues: N-methylation leads the way
Dipendu Das, Hina P. A. Khan, Rahul Shivahare, Suman Gupta, Jayanta Sarkar, Mohd. Imran Siddiqui, Ravi Sankar Ampapathi and Tushar Kanti Chakraborty  
DOI: 10.1039/C6OB02610A, Paper

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JA-Ile-macrolactones uncouple growth and defense in wild tobacco
Guillermo H. Jimenez-Aleman, Ricardo A. R. Machado, Ian T. Baldwin and Wilhelm Boland  
DOI: 10.1039/C7OB00249A, Communication

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Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis
Vishal M. Sheth, Bor-Cherng Hong and Gene-Hsiang Lee  
DOI: 10.1039/C7OB00473G, Communication

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Synthesis of AHMOD-containing aminolipopeptides, unique bioactive peptaibiotics
Louise A. Stubbing, Iman Kavianinia and Margaret A. Brimble  
DOI: 10.1039/C7OB00541E, Review Article

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Enantioselective total synthesis of colomitides and their absolute configuration determination and structural revision
Hongguang Yang, Xiaoyu Liu, Xiaoyu Li, Xiang Shi, Feilong Yang, Xiaozhen Jiao and Ping Xie  
DOI: 10.1039/C7OB00539C, Paper

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Biochemical studies of inositol N-acetylglucosaminyltransferase involved in mycothiol biosynthesis in Corynebacterium diphtheria
Yuchuan Guo, Lizhen Wang, Jiatong Guo, Guofeng Gu and Zhongwu Guo  
DOI: 10.1039/C7OB00555E, Paper

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Dissection of the neocarazostatin: a C4 alkyl side chain biosynthesis by in vitro reconstitution
Li Su, Rui Zhang, Kwaku Kyeremeh, Zixin Deng, Hai Deng and Yi Yu  
DOI: 10.1039/C7OB00617A, Communication

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Rifamorpholines A–E, potential antibiotics from locust-associated actinobacteria Amycolatopsis sp. Hca4
Yong Sheng Xiao, Bo Zhang, Mei Zhang, Zhi Kai Guo, Xin Zhao Deng, Jing Shi, Wei Li, Rui Hua Jiao, Ren Xiang Tan and Hui Ming Ge  
DOI: 10.1039/C7OB00614D, Paper

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Asymmetric synthesis of ent-fragransin C1
Santikorn Chaimanee, Manat Pohmakotr, Chutima Kuhakarn, Vichai Reutrakul and Darunee Soorukram  
DOI: 10.1039/C7OB00749C, Paper

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