Author Archive

Editor’s Collection: Christian Hackenberger

The Organic & Biomolecular Chemistry Editor’s collection is a showcase of some of the best articles published in the journal, hand selected by our Associate Editors and Editorial Board members. For this inaugural selection, Associate Editor Christian Hackenberger has highlighted some of his favourite recent works. Take a look at what he thought of the articles below, and find out more about the research and the researchers behind the papers in our interviews with the authors.

Christian’s Selection:

Hierarchical self-assembly of an azobenzene dyad with inverted amide connection into toroidal and tubular nanostructures

Christian’s comments: “Small things can make a difference! Check out this very interesting paper by Yagai et al on how inverting an amide bond in foldable azobenzene dyads changes the thermal stability of self-assembled toroids and nanotubes! Amazing! This paper is part of our collection Supramolecular chemistry in OBC.

 

Find out more in our interview with the authors

 

Rapid sodium periodate cleavage of an unnatural amino acid enables unmasking of a highly reactive α-oxo aldehyde for protein bioconjugation

Christian‘s comments: “Now available site-specifically! This contribution by Fascione and coworkers expands the use of Strain-Promoted Alkyne-Nitrone Cycloaddition (SPANC) ligation to modify internal α-oxo aldhehydes in proteins. Particularly remarkable is that this work describes a rare example of site-specifically incorporated aldehyde into proteins via amber stop codon suppression. Well done folks!

 

Find out more in our interview with the authors

 

Site-selective modification of proteins using cucurbit[7]uril as supramolecular protection for N-terminal aromatic amino acids

Christian‘s comments: “A supramolecular protecting group in peptide and protein chemistry! This paper I handled myself and I agree with the reviewers that this is a nice piece of work. Appel and coworkers make clever use of cucurbit[7]uril, which blocks the nucloephilicity of an N-terminal phenylalanine. Quite handy for the selective modification of the N-terminal glycine of the A-chain in insulin!

Find out more in our interview with the authors

 

Disulphide-mediated site-directed modification of proteins

Christian’s comments: “Gothelf and Clo from Aarhus University and Novo Nordisk report in this paper the modification of lysines in pharmaceutically relevant proteins and antibody fragments. What is special about their work is that only lysines are modified in proximity to solvent-exprosed disulfides by clever design of a bifunctional reagent, which consits of a rebridging moiety, a masked thiol and an amine reactive group. One can only wish that more of such innovative collaborations between industry and academia are reported.

Find out more in our interview with the authors

 

The Curious Yellow Colouring Matter of the Iceland Poppy

Christian’s comments: “And finally an awesome historical overview on an intruiging yellow colored natural product, the nudicaulin. This flavoalkaloid was named by Sir Robert Robinson in 1939. Devlin and Sperry take the reader through a fascinating journey on the first structural assignment, synthesis strategies, biosynthesis and biological role. A must read not only for the natural product chemists among us!

Find out more in our interview with the authors

 

Meet the Editor:

Christian P. R. Hackenberger completed his graduate studies in chemistry at the universities of Freiburg and UW Madison and his doctoral studies in 2003 at the RWTH Aachen. After a postdoctoral position at MIT, he started his own group at the Freie Universität Berlin in 2005. In 2012, he was appointed Leibniz-Humboldt Professor for Chemical Biology at the Leibniz-Research Institute for Molecular Pharmacology and the Humboldt Universität zu Berlin.

His group works on the development of new chemoselective and bioorthogonal reactions, the identification and analysis of novel PTMs, the engineering of protein-based pharmaceuticals and novel approaches to functional protein synthesis and delivery, in particular for the labeling and modification of different antibody formats. He is co-founder of the recently founded company ‘Tubulis’, which ventures into engineering better tolerable cancer drugs based on protein- and antibody-drug conjugates.

Christian is an Associate Editor for Organic & Biomolecular Chemistry since 2015 and on the Advisory board of Chemical Science and RSC Chemical Biology. His research group can be followed on Twitter @PhosphorusFive.

Outside his chemistry life he enjoys all forms of sport (Federer!), foodie (Ottolenghi!) and cultural (Theatre! Contemporary Art! Opera!) activities.

 

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Outstanding Reviewers for Organic & Biomolecular Chemistry in 2019

We would like to highlight the Outstanding Reviewers for Organic & Biomolecular Chemistry in 2019, as selected by the editorial team, for their significant contribution to the journal. The reviewers have been chosen based on the number, timeliness and quality of the reports completed over the last 12 months.

We would like to say a big thank you to those individuals listed here as well as to all of the reviewers that have supported the journal. Each Outstanding Reviewer will receive a certificate to give recognition for their significant contribution.

 

Prof. Dr. Jeroen Dickschat, University of Bonn, ORCHID: 0000-0002-0102-0631

Dr Jianlin Han, Nanjing Forestry University, ORCHID: 0000-0002-3817-0764

Professor Erhong Hao, Anhui Normal University, ORCHID: 0000-0001-7234-4994

Dr Mohammed Hasan, Tallinn University of Technology, ORCHID: 0000-0001-5683-6673

Prof. Dr. Hans-Joachim Knölker, Technische Universität Dresden, ORCHID: 0000-0002-9631-5239

Dr Rafal Loska, Polish Academy of Sciences, ORCHID: 0000-0002-0823-4675

Professor Vaibhav P. Mehta, Marwadi University, ORCHID: 0000-0003-4426-3374

Dr Tej Narayan Poudel, University of Minnesota, ORCHID: 0000-0002-0390-107X

Professor Akhilesh K. Verma, University of Delhi, ORCHID: 0000-0001-7626-5003

Dr Chunxiang Wang, Takeda Pharmaceutical Co Ltd, ORCHID: 0000-0002-8669-1767

 

We would also like to thank the Organic & Biomolecular Chemistry board and the organic chemistry community for their continued support of the journal, as authors, reviewers and readers.

 

If you would like to become a reviewer for our journal, just email us with details of your research interests and an up-to-date CV or résumé.  You can find more details in our author and reviewer resource centre

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OBC proudly supports the Chemical Biology and Physiology Conference

Organic & Biomolecular Chemistry and our sister journals, Chemical Science and RSC Advances, are proud to sponsor the upcoming Chemical Biology and Physiology Conference, 12-15 December 2019 at Oregon Health & Science University.

The Chemical Biology and Physiology Conference series is a biennial international conference focused on the growing intersection of Chemical Biology and Physiology, bringing together leading scientists from around the world to promote the inspiration and collaboration to stimulate cutting edge research in this exciting research nexus. The fantastic speaker line up includes Benjamin Cravatt, Laura Kiessling, Tom Muir, Jennifer Heemstra and more. This year’s topics of focus include Chemical Physiology, Imaging, Glyco Chemical Biology, Nucleotide Chemical Biology, Optical Tools and Protein Magic.

To find out more and register before the abstract deadline (October 31) or final deadline (November 15), visit www.ohsu.edu/chembiophys2019.

 

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OBC Highlights: A transition metal-free strategy for the desulfonative borylation of benzyl sulfones

Compounds containing carbon-boron bonds are of high significance because they can be used as the precursors for various reactions such as 1,2-metallate rearrangements, deborylative nucleophilic addition reactions and the formation of carbon-oxygen and carbon-nitrogen bonds through hydrolysis and aminolysis respectively. Sulfones are useful for increasing the functionality of a molecule by alkylation and arylation (scheme 1), however till date there have been very few reports regarding the transformation of carbon-sulfonyl bonds to carbon-boron bonds. The transformation of sulfonyl groups to boryl groups under metal free organocatalysis is still a challenging task.

Scheme 1: Sequential functionalization of benzylic sulfones

In their recent OBC publication, Prof Cathleen M. Crudden et.al. of Queen’s University, Ontario developed a beautiful protocol for the transition metal-free desulfonative borylation of benzyl sulfones using simple pyridine derivatives as catalysts (scheme 2). They reported the borylation of cyclic sulfones to afford functionalized sulfones and sulfonamides through a sulfinate intermediate which could be trapped with electrophiles. As they chose benzhydryl phenyl sulfone (1a) as a model substrate for their optimization, they reported the formation of the desired dibenzylic boronic (2a) ester along with diphenylmethane (3a) as a by-product. By using trifluorotoluene as a solvent instead of ethereal solvents, they optimized their conditions, resulting in an enhanced formation of 2a and supressed formation of 3a.

 

Scheme 2: Pyridine-promoted desulfonative borylation of benzyl sulfones

The reaction was well tolerated by a range of benzhydryl sulfones bearing both electron-neutral and electron-rich aryl groups with good yields. Even sterically hindered ortho-substituted aryl groups also afforded the desired products with lower yields. Unfortunately, benzhydryl sulfones bearing electron-withdrawing substituents such as trifluoromethyl, esters, cyano, allyl and iodide groups were not tolerated the transformation. Crudden et. al. executed control experiments in order to understand the reaction mechanism, finding that the sulfone bearing terminal olefin did not afford any product and also that TEMPO ((2,2,6,6-Tetramethylpiperidin-1-yl)oxyl) completely inhibited borylation. Based on these observations, they proposed a single electron transfer mechanism for borylation based on the work from Tuttle and Zhang and Jiao.

In conclusion, Crudden et al. succeeded in developing a desulfonylative borylation of alkyl sulfon es through 4-arylpyridine catalysis which yields synthetically useful benzylic boron compounds.

Read their full article now.

About the Blog Writer: A. Vamshi Krishna is currently pursuing a Ph.D. in organic chemistry with Prof. D. B. Ramachary at University of Hyderabad. His research mainly focuses on asymmetric supramolecular-organocatalysis, where he synthesises highly functionalized biologically active novel scaffolds with excellent selectivities and yields. His passion for scientific writing made him become a blog writer.

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OBC Highlight: Trifluoromethylated proline analogues through highly diastereoselective formal (3+2) cycloadditions

Amino acids form the fundamental building blocks of proteins and peptides and largely control the biochemical and biophysical properties of a living organism. Incorporation of fluorine in amino acids has been an area of wide interest, because replacement of a hydrogen atom with a fluorine atom leads to a significant change in the electronic properties of a substrate and could potentially lead to a wide variation in its biological activity. The most common functional group introduced in this regard is the trifluoromethyl (-CF3) group, which provides an alternative to the -CH3 group in terms of its electronic properties. One very commonly available source of the -CF3 group is ethyl 3,3,3-trifluoromethyl pyruvate, which was utilized very elegantly by Professor Mario Waser and his group in their recent report published from the Johannes Kepler University, Linz to form α-trifluoromethylated proline derivatives, which are potentially very interesting surrogates for naturally occurring proline.

Scheme 1: Diastereoselective formal (3+2) cyclization to form α-CF3 proline derivatives

Benzyl imine derived from ethyl 3,3,3-trifluoromethyl pyruvate was treated with benzylidene indanedione (1) in the presence of LiOH to form the spirocyclic α-trifluoromethyl proline derivative 3 as the sole diastereomer (Scheme 1). It was observed that simple ammonium salts used as phase transfer catalysts could improve the conversion drastically and benzyl triethylammonium bromide (TEBAB) was found to be the best reagent for the same. This transformation exhibits a wide substrate scope with different acceptors and donors alike, while maintaining very good diastereoselectivities.

Mechanistically, the transformation is driven by the formation of the stable 2-azaallyl carbanions (4 and 4’), which by virtue of its two resonating forms could form the two different spirocyclic regioisomers 3 and 5 (Scheme 2). It was observed that the α-nucleophilic attack on the Michael acceptor 1 proceeded exclusively and there was no trace of the γ-adduct for any of the substrates. The remarkable levels of diastereoselectivity of the α-adducts adds to the ingenuity of the method.

Scheme 2: Formal (3+2) cyclization modes leading to α-CF3 proline derivatives

This is indeed a very useful and efficient method for the construction of an unprecedented class of α-trifluoromethylated proline derivatives which can easily be incorporated in peptide chains for biological studies. There is however, room for improvement in this methodology, as the efforts towards enantioselective formation of the trifluoromethylated proline derivatives were unfortunately met with failures. The authors used cinchona alkaloid derived chiral phase transfer catalysts, which resulted in unsatisfactory enantioselectivities. A successful enantioselective protocol towards the formation of fluorinated amino acids would drive this field of research even further in future.

About the blog writer: Satrajit Indu is a recent PhD graduate from Indian Institute of Technology Bombay. His doctoral work in the group of Prof. Krishna P. Kaliappan was mainly focused on the total synthesis of complex natural products and development of new catalytic methods aimed for achieving interesting chemical transformations. A keen interest in organic chemistry coupled with an urge to communicate with the scientific community has driven him to take up blog writing.

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OBC Highlight: Planarized and structurally constrained B,N-phenylated dibenzoazaborine: diversity in electronic properties

Polycyclic aromatic hydrocarbons (PAHs) containing heteroatoms have recently been grabbing the attention of scientists as they exhibit intriguing photophysical properties and can be widely used as building blocks for π-conjugated materials due to the effect of heteroatoms on the electronic properties of the system.

PAHs are often employed in OLEDs. Over the last few years, these PAHs have been synthesized in several different ways. Kawashima et.al synthesized different acene-like π-extended dibenzoborines such as compound B which show fascinating photophysical properties. More recently, Hatakeyama et.al have reported the synthesis of various PAHs that contain multiple 1,4-azaborine rings, such as compound C, which show excellent thermally activated delayed fluorescence. By investigating these types of molecules in more detail, their electronic properties can be improved to make better OLEDs.

a) Representative examples of previously reported dibenzoazaborine-based pi-conjugated compounds and b) planarized B,N-phenylated dibenzoazaborine 1 together with reference compounds 2-4

a) Representative examples of previously reported dibenzoazaborine-based pi-conjugated compounds and b) planarized B,N-phenylated dibenzoazaborine 1 together with reference compounds 2-4

a) UV-vis absorption and b) fluorescence spectra of 1 (red), 2 (blue), 3 (green) and 4 (orange) in THF.

a) UV-vis absorption and b) fluorescence spectra of 1 (red), 2 (blue), 3 (green) and 4 (orange) in THF.

In their recent OBC publication, Professor Shigehiro Yamaguchi of the Institute of Transformative Bio- Molecules, Nagoya University et al. explored in detail the relation between the structure of materials and their electronic structures. They mainly focused on the correlation between the ring-fusion mode, where two cyclic rings fused in a planar manner, and the degree of structural constraint within the dibenzoazaborine skeleton. As constraining molecules into a planar fashion can extend π-conjugation and increase chemical stability, Shigehiro planarized the B-, N- phenyl groups in dibenzoazaborine to synthesize a new family of planarized triarylboranes with a carbazole substructure, confirming this structure by single-crystal X-ray diffraction analysis. They studied the photophysical properties of 1 and compared it with compunds 2-4. Compound 1 showed an intense absorption band at λabs= 402 nm unlike compounds 2-4 which showed λabs at 389 and 371, 400, 404 and 387 nm respectively. The fluorescence spectra of compound 1 showed an intense deep blue emission with a full width at half maximum (FWHM) of 27 nm which is due to its rigid structure. The optimized structure of 1 with respect to DFT calculations matched with the experimentally determined crystal structure. They report the time dependent DFT calculations which prove compound 1 to have the highest oscillator strength (f) amongst compounds 1-4, resulting in the largest molar absorption coefficient (ε). This clearly represents that it absorbs light strongly at the given wavelength. They also studied the electrochemical properties of 1-4 using cyclic voltammetry which resulted in one reversible reduction wave irrespective of the structural constraint showing that there are no electronic effects imposed on the structural constraint.

In conclusion, Shigehiro et al. succeeded in synthesizing structurally constrained, planarized dibenzoazaborines and investigating their photophysical and electronic effects.

Read their full article at https://rsc.li/2Xw8uoA.

Blog writer description: I am A. Vamshi Krishna, pursuing a PhD in organic chemistry with Prof. D. B. Ramachary at the University of Hyderabad. My research mainly focuses on asymmetric supramolecular-organocatalysis where we synthesise highly functionalized biologically active novel scaffolds with excellent selectivity and yields. I am passionate about scientific writing.

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Organic & Biomolecular Chemistry welcomes new Associate Editor Elizabeth Krenske

New OBC Associate Editor Elizabeth Krenske

We are delighted to welcome Dr Elizabeth Krenske to the OBC team as an Associate Editor. Elizabeth is an Associate Professor at the University of Queensland, Australia, where her research focuses on the computational study of organic reactions and modelling of drug molecules and interactions.

After starting out her career in chemistry as an undergraduate at the University of Queensland, Elizabeth undertook a PhD in the field of synthetic main-group chemistry at The Australian National University’s Research School of Chemistry, under the supervision of Professor S. Bruce Wild. She spent a further two years carrying out postdoctoral research at the Australian National University, before receiving a Fulbright Scholarship and commencing postdoctoral studies at UCLA with Ken Houk. Elizabeth returned to Australia in 2009 as an Australian Research Council (ARC) Australian Postdoctoral Fellow at the University of Melbourne, and moved to The University of Queensland in 2012 as an ARC Future Fellow. She is currently an Associate Professor and Strategic Research Fellow in the University of Queensland School of Chemistry and Molecular Biosciences. To find out more about Elizabeth and her research, visit her webpage or browse some of her recent publications below.

 

Elizabeth’s recent publications:

 

The fate of copper catalysts in atom transfer radical chemistry

Polym. Chem., 2019, 10, 1460-1470

 

Asymmetric synthesis of multiple quaternary stereocentre-containing cyclopentyls by oxazolidinone-promoted Nazarov cyclizations

Chem. Sci., 2018, 9, 4644-4649

 

Synthesis of spirocyclic orthoesters by ‘anomalous’ rhodium(II)-catalysed intramolecular C–H insertions

Org. Biomol. Chem., 2018, 16, 256-261

 

Claisen rearrangements of benzyl vinyl ethers: theoretical investigation of mechanism, substituent effects, and regioselectivity

Org. Biomol. Chem., 2017, 15, 7887-7893

 

An unprecedented stereoselective base-induced trimerization of an α-bromovinylsulfone

Org. Biomol. Chem., 2017, 15, 5529-5534

 

Submit your research to Elizabeth now!
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OBC Highlight: A new atom and mass efficient synthetic route for tamoxifen

Nowadays, chemists are increasingly interested in revealing simpler methodologies for the synthesis of various drugs with high selectivity and purity. Transition metal catalysis has opened a wide window for the synthesis of different natural products and drugs with greater ease.

Z-Tamoxifen is one such drug, which is used in the treatment of breast cancer. Although there are many well-established synthetic procedures for the synthesis of Z-tamoxifen by various research groups such as T. Stiidemann et.al. and P. L. Coe et.al. etc., there are disadvantages to current methods, such as the use of multiple synthetic steps and generation of stoichiometric amounts of waste. Thus, there is a need to overcome these drawbacks.

In their recent OBC publication, Prof. Ben L. Feringa et.al. of Stratingh Institute for Chemistry, University of Groningen, Nijenborgh develop a fantastic two step protocol for the synthesis of Z-tamoxifen from commercially available starting materials. Usually, the transmetallation of anions formed by carbolithiation of (diphenyl)acetylenes with magnesium, boron, zinc or aluminium results in an active cross coupling partner, but with low atom efficiency. Here, Feringa et.al., for the first time proposed the direct cross coupling of the formed organolithium reagent with aryl halides in the presence of an active palladium nanoparticle based catalyst, cutting down the number of synthetic steps required to two, with excellent selectivities and yields. They report the thorough screening of reaction conditions such as solvent, temperature, catalyst loading etc. and explain the effect of various reaction parameters. The 0.67 atom economy and 22% RME achieved in the study is twice as good as the previously reported best protocol, and the scientists found that THF gave the desired product without encouraging any side reactions. Another advantage of this reaction is that the formed side product (lithium halide) can be easily removed.

Hence, Prof. Ben L. Feringa laid a new efficient pathway for the synthesis of biologically important Z-tamoxifen through his works.

Read their full article now.

 

About the Blog Writer: A. Vamshi Krishna is currently pursuing a PhD  in Organic chemistry with Prof. D. B. Ramachary at University of Hyderabad. His research mainly focuses on asymmetric supramolecular catalysis and organocatalysis, where he synthesises highly functionalized biologically active novel scaffolds with excellent selectivities and yields. He is passionate about scientific writing.

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Editor’s Choice: Santanu’s recommended articles

Professor Santanu Mukherjee (Indian Institute of Science, Bangalore), recently joined the Organic & Biomolecular Chemistry team as an Associate Editor. Santanu works in the field of asymmetric catalysis, with a focus on the discovery of new enantioselective transformations. His research group investigates hydrogen bonding, Lewis base and bifunctional catalysis, and more recently, he has focused on iridium-catalyzed asymmetric allylic substitution reactions.

 

To find out more about Santanu, take a look at our recent blog welcoming him to the team.

 

Santanu has picked out a selection of his personal favourite recent OBC articles which you can read now for free*

 

Santanu’s Recommended OBC Articles:

 

Catalyst-controlled positional-selectivity in C–H functionalizations

Virendra Kumar Tiwari and Manmohan Kapur

 

 

 

An enantioselective synthesis of α-alkylated pyrroles via cooperative isothiourea/palladium catalysis

W. Rush Scaggs, Toya D. Scaggs and Thomas N. Snaddon

 

Organocatalytic asymmetric synthesis of highly substituted pyrrolidines bearing a stereogenic quaternary centre at the 3-position

Soumendranath Mukhopadhyay and Subhas Chandra Pan

 

Total synthesis of incargranine A

Patrick D. Brown and Andrew L. Lawrence

 

 

 

 

Studies toward the synthesis of strevertenes A and G: stereoselective construction of C1–C19 segments of the molecules

Tapan Kumar Kuilya, Subhendu Das, Dhiman Saha and Rajib Kumar Goswami

 

Formal [4 + 2] benzannulation of 2-alkenyl indoles with aldehydes: a route to structurally diverse carbazoles and bis-carbazoles

Ankush Banerjee, Avishek Guin, Shuvendu Saha, Anushree Mondal and Modhu Sudan Maji

 

Vinylogous acyl triflates as an entry point to α,β-disubstituted cyclic enones via Suzuki–Miyaura cross-coupling

Daria E. Kim, Yingchuan Zhu and Timothy R. Newhouse

 

 

 

 

*Access is free until 28/02/2019 through a registered RSC account.

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OBC warmly welcomes Professor Anthony Davis as our new Editorial Board Chair

We are delighted to announce the appointment of Prof. Anthony Davis as the new Organic & Biomolecular Chemistry Editorial Board Chair. Tony returns to the Board after serving for many years as an Editorial Board member and we are very pleased to welcome him to his new role as Chair.

 

Tony is a Professor of Supramolecular Chemistry at the University of Bristol, with research focusing on anion recognition and transport, carbohydrate recognition, and crystal engineering. He started his chemistry career at Oxford University, obtaining both his undergraduate degree and D.Phil (in the group of Dr Gordon Whitham), followed by two years of postdoctoral work under the supervision of Prof. Jack Baldwin. He joined the group of Prof. Albert Eschenmoser in 1981, working as a Royal Society European Exchange Fellow, before becoming a Lecturer in Organic Chemistry at Trinity College, Dublin, in 1982. In September 2000, he moved to his current institution, and you can find out more about his current group on the research group webpage.

 

Tony is also a co-founder of Ziylo, a biotechnology company focusing on the development of new treatments for diabetes patients, which was recently sold to Novo Nordisk. A second company spun out of Ziylo, Carbometrics, continues to work on carbohydrate sensing.

 

Prof. Davis is the recipient of numerous awards including the Tilden Medal and the RSC Award for Physical Organic Chemistry. He has published hundreds of articles, and you can see a selection of his great work below.

 

Upon becoming Chair, Tony commented, “OBC is a cornerstone of organic chemical publishing, and I’m delighted to take on this responsibility.”

 

Read some of Tony’s latest publications:

Maltodextrin recognition by a macrocyclic synthetic lectin

Chem. Commun., 2018, 54, 8649-8652

 

Anion transport by ortho-phenylene bis-ureas across cell and vesicle membranes

Org. Biomol. Chem., 2018, 16, 1083-1087

(Included in the 2018 OBC HOT article collection)

 

Enantioselective carbohydrate recognition by synthetic lectins in water

Chem. Sci., 2017, 8, 4056-4061

 

Synthesis and evaluation of a desymmetrised synthetic lectin: an approach to carbohydrate receptors with improved versatility

Org. Biomol. Chem., 2016, 14, 1930-1933

(Included in the 2016 OBC HOT article collection)

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