Natural Products Blog

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

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:

One-pot quadruple/triple reaction sequence: a useful tool for the synthesis of natural products
K. Kashinath and D. Srinivasa Reddy
Org. Biomol. Chem., 2015,13, 970-973
DOI: 10.1039/C4OB02143F, Perspective

Formation of the steroidal C-25 chiral center via the asymmetric alkylation methodology
Yu. V. Ermolovich, V. N. Zhabinskii and V. A. Khripach
Org. Biomol. Chem., 2015,13, 776-782
DOI: 10.1039/C4OB02123A, Paper

Functional importance of the sugar moiety of jasmonic acid glucoside for bioactivity and target affinity
Minoru Ueda, Gangqiang Yang, Yuuki Nukadzuka, Yasuhiro Ishimaru, Satoru Tamura and Yoshiyuki Manabe
Org. Biomol. Chem., 2015,13, 55-58
DOI: 10.1039/C4OB02106A, Communication

Synthesis of fully functionalized aglycone of lycoperdinoside A and B
Balla Chandrasekhar, Sudhakar Athe, P. Purushotham Reddy and Subhash Ghosh
Org. Biomol. Chem., 2015,13, 115-124
DOI: 10.1039/C4OB01716A, Paper

Biosynthesis of 8-hydroxyquinoline-2-carboxylic acid, an iron chelator from the gut of the lepidopteran Spodoptera littoralis
Jelena Pesek, Jiří Svoboda, Martina Sattler, Stefan Bartram and Wilhelm Boland
Org. Biomol. Chem., 2015,13, 178-184
DOI: 10.1039/C4OB01857E, Paper

Synthesis of maculalactone A and derivatives for environmental fate tracking studies
Samuel L. Bader, Michael U. Luescher and Karl Gademann
Org. Biomol. Chem., 2015,13, 199-206
DOI: 10.1039/C4OB02042A, Paper

An enantioselective total synthesis of Sch-725674
Kota Ramakrishna and Krishna P. Kaliappan
Org. Biomol. Chem., 2015,13, 234-240
DOI: 10.1039/C4OB02136C, Paper

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

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:

Non-isoprenoid polyene natural products – structures and synthetic strategies
Katrina S. Madden, Fathia A. Mosa and Andrew Whiting
Org. Biomol. Chem., 2014,12, 7877-7899
DOI: 10.1039/C4OB01337A, Review Article

Catalytic asymmetric synthesis of the pentacyclic core of (−)-nakadomarin A via oxazolidine as an iminium cation equivalent
Nobuya Tsuji, Michael Stadler, Naoya Kazumi, Tsubasa Inokuma, Yusuke Kobayashi and Yoshiji Takemoto
Org. Biomol. Chem., 2014,12, 7919-7922
DOI: 10.1039/C4OB01678E, Communication

A one-pot multicomponent coupling/cyclization for natural product herbicide (±)-thaxtomin A
Jean Paul Bourgault, Amarendar Reddy Maddirala and Peter R. Andreana
Org. Biomol. Chem., 2014,12, 8125-8127
DOI: 10.1039/C4OB01148A, Communication

Regiodivergent and short total synthesis of calothrixins
Dipakranjan Mal, Joyeeta Roy and Kumar Biradha
Org. Biomol. Chem., 2014,12, 8196-8203
DOI: 10.1039/C4OB01309C, Paper

Asymmetric total synthesis of paecilomycin E, 10′-epi-paecilomycin E and 6′-epi-cochliomycin C
Pratik Pal, Nandan Jana and Samik Nanda
Org. Biomol. Chem., 2014,12, 8257-8274
DOI: 10.1039/C4OB01400F, Paper

The first stereoselective total synthesis of neosemburin and isoneosemburin
Gadi Madhusudhan Reddy and Perali Ramu Sridhar
Org. Biomol. Chem., 2014,12, 8408-8414
DOI: 10.1039/C4OB01239A, Paper

ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels–Alder reactions: synthesis of dihydropyran-fused diterpenoids
Chunyong Ding, Lili Wang, Haijun Chen, Christopher Wild, Na Ye, Ye Ding, Tianzhi Wang, Mark A. White, Qiang Shen and Jia Zhou
Org. Biomol. Chem., 2014,12, 8442-8452
DOI: 10.1039/C4OB01040J, Paper

The amphiphilic nature of saponins and their effects on artificial and biological membranes and potential consequences for red blood and cancer cells
Joseph H. Lorent, Joëlle Quetin-Leclercq and Marie-Paule Mingeot-Leclercq
Org. Biomol. Chem., 2014,12, 8803-8822
DOI: 10.1039/C4OB01652A, Review Article

Structures, chemotaxonomic significance, cytotoxic and Na+,K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica
Rong-Rong Zhang, Hai-Yan Tian, Ya-Fang Tan, Tse-Yu Chung, Xiao-Hui Sun, Xue Xia, Wen-Cai Ye, David A. Middleton, Natalya Fedosova, Mikael Esmann, Jason T. C. Tzen and Ren-Wang Jiang
Org. Biomol. Chem., 2014,12, 8919-8929
DOI: 10.1039/C4OB01545B, Paper

The protecting-group directed diastereoselective Nozaki–Hiyama–Kishi (NHK) reaction: total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues
Debendra K. Mohapatra, D. Sai Reddy, N. Arjunreddy Mallampudi, Janardhan Gaddam, Sowjanya Polepalli, Nishant Jain and J. S. Yadav
Org. Biomol. Chem., 2014,12, 9683-9695
DOI: 10.1039/C4OB01811G, Paper

Total synthesis and biological evaluation of the natural product (−)-cyclonerodiol, a new inhibitor of IL-4 signaling
Jens Langhanki, Kristina Rudolph, Gerhard Erkel and Till Opatz
Org. Biomol. Chem., 2014,12, 9707-9715
DOI: 10.1039/C4OB02021A, Paper

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

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:

Nitroso Diels–Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products
Serena Carosso and Marvin J. Miller
Org. Biomol. Chem., 2014, 12, 7445-7468
DOI: 10.1039/C4OB01033G, Review Article

Approaches to the total synthesis of chaetochalasin A
Eric J. Thomas and Mark Willis
Org. Biomol. Chem., 2014, 12, 7537-7550
DOI: 10.1039/C4OB01308E, Paper
From themed collection In Celebration of Richard Taylor’s 65th Birthday

Total synthesis and biological studies of cryptocin and derivatives of equisetin and fusarisetin A
Lili Kong, Mingjin Rao, Jinjie Ou, Jun Yin, Weiqiang Lu, Mingyao Liu, Xiufeng Pang and Shuanhu Gao
Org. Biomol. Chem., 2014, 12, 7591-7597
DOI: 10.1039/C4OB01149J, Paper

A new approach to asymmetric synthesis of infectocaryone
Xiubing Liu, Lingling Hu, Xiaojing Liu, Junhao Jia, Lizhen Jiang, Jiangfeng Lin and Xiaochuan Chen
Org. Biomol. Chem., 2014, 12, 7603-7611
DOI: 10.1039/C4OB01162G, Paper

The first synthesis of the antiangiogenic homoisoflavanone, cremastranone
Bit Lee, Halesha D. Basavarajappa, Rania S. Sulaiman, Xiang Fei, Seung-Yong Seo and Timothy W. Corson
Org. Biomol. Chem., 2014, 12, 7673-7677
DOI: 10.1039/C4OB01604A, Communication

Total synthesis and biological evaluation of atrop-O-benzyl-desmethylabyssomicin C
R. Matovic, F. Bihelovic, M. Gruden-Pavlovic and R. N. Saicic
Org. Biomol. Chem., 2014, 12, 7682-7685
DOI: 10.1039/C4OB01436G, Communication

Linear synthesis of the branched pentasaccharide repeats of O-antigens from Shigella flexneri 1a and 1b demonstrating the major steric hindrance associated with type-specific glucosylation
Jason M. Hargreaves, Yann Le Guen, Catherine Guerreiro, Karine Descroix and Laurence A. Mulard
Org. Biomol. Chem., 2014, 12, 7728-7749
DOI: 10.1039/C4OB01200C, Paper

Theoretical insight into the antioxidant properties of melatonin and derivatives
Jeffrey R. Johns and James A. Platts
Org. Biomol. Chem., 2014, 12, 7820-7827
DOI: 10.1039/C4OB01396D, Paper

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

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?

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:

Biomimetic total synthesis of (±)-yezo’otogirin A
Hiu C. Lam, Kevin K. W. Kuan and Jonathan H. George
Org. Biomol. Chem., 2014,12, 2519-2522
DOI: 10.1039/C4OB00186A, Communication

Complexity generation by chemical synthesis: a five-step synthesis of (−)-chaetominine from L-tryptophan and its biosynthetic implications
Chu-Pei Xu, Shi-Peng Luo, Ai-E Wang and Pei-Qiang Huang
Org. Biomol. Chem., 2014,12, 2859-2863
DOI: 10.1039/C4OB00314D, Communication

A unified strategy for the synthesis of the C1–C14 fragment of marinolic acids, mupirocins, pseudomonic acids and thiomarinols: total synthesis of pseudomonic acid methyl monate C
Y. Sridhar and P. Srihari
Org. Biomol. Chem., 2014,12, 2950-2959
DOI: 10.1039/C4OB00025K, Paper

Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening rearrangement
Dandan Liu, Long Ai, Fan Li, Annan Zhao, Jingbo Chen, Hongbin Zhang and Jianping Liu
Org. Biomol. Chem., 2014,12, 3191-3200
DOI: 10.1039/C4OB00126E, Paper

The nature of persistent conformational chirality, racemization mechanisms, and predictions in diarylether heptanoid cyclophane natural products
Ommidala Pattawong, M. Quamar Salih, Nicholas T. Rosson, Christopher M. Beaudry and Paul Ha-Yeon Cheong
Org. Biomol. Chem., 2014,12, 3303-3309
DOI: 10.1039/C3OB42550A, Paper

Rare Streptomyces sp. polyketides as modulators of K-Ras localisation
Angela A. Salim, Xue Xiao, Kwang-Jin Cho, Andrew M. Piggott, Ernest Lacey, John F. Hancock and Robert J. Capon
Org. Biomol. Chem., 2014,12, 4872-4878
DOI: 10.1039/C4OB00745J, Paper

A total synthesis of (+)-negamycin through isoxazolidine allylation
Roderick W. Bates, Rab’iah Nisha Khanizeman, Hajime Hirao, Yu Shan Tay and Patcharaporn Sae-Lao
Org. Biomol. Chem., 2014,12, 4879-4884
DOI: 10.1039/C4OB00537F, Paper

Mechanistic studies for tri-targeted inhibition of enzymes involved in cholesterol biosynthesis by green tea polyphenols Hu Ge, Jinggong Liu, Wenxia Zhao, Yu Wang, Qingqing He, Ruibo Wu, Ding Li and Jun Xu
Org. Biomol. Chem., 2014,12, 4941-4951
DOI: 10.1039/C4OB00589A, Paper

Iodine-catalyzed aromatization of tetrahydrocarbazoles and its utility in the synthesis of glycozoline and murrayafoline A: a combined experimental and computational investigation
Vivek Humne, Yuvraj Dangat, Kumar Vanka and Pradeep Lokhande
Org. Biomol. Chem., 2014,12, 4832-4836
DOI: 10.1039/C4OB00635F, Communication

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