Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• which substituents can easily be introduced. From a chemical synthesis point of view, the reactivity difference between the primary and secondary hydroxy groups allows selective functionalization on the narrow or the wider edge of the truncated cone (Table 1). Access to the gamut of functional groups

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

• Vladimir A. Stepchenko,
• Anatoly I. Miroshnikov,
• Frank Seela and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254

• chemical synthesis and investigation of their physicochemical and biological properties (early works are reviewed in [1][2]). Studies on thioxo- and azapyrimidine nucleosides are an inspiring subject of investigation due to their very special biochemical [3][4][5][6][7] and biophysical properties in

• antiviral activity in various experiments [15][16][17][18][19][20][21][22]. Regarding the chemical synthesis of this class of pyrimidine nucleosides various approaches were published (see, e.g., [8][9][10][11][14][15][16][23][24]; reviewed by Vorbrüggen and Ruh-Pohlenz [25]). On the contrary, only few

• differences of tautomeric structures of pyrimidines studied and their recognition by E. coli UP vs TP in the glycoside bond formation: Activation of uracil and thymine as well as their related analogues in the chemical synthesis of nucleosides consists in the trimethylsilylation giving rise to the formation

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

• Kirsty L. Wilson,
• Alan R. Kennedy,
• Jane Murray,
• Ben Greatrex,
• Craig Jamieson and
• Allan J. B. Watson

Beilstein J. Org. Chem. 2016, 12, 2005–2011, doi:10.3762/bjoc.12.187

• solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis. Herein, we describe the scope and limitations of an alternative to DMF derived from renewable sources (CyreneTM) in Sonogashira cross-coupling and Cacchi-type annulations

The in situ generation and reactive quench of diazonium compounds in the synthesis of azo compounds in microreactors

• Faith M. Akwi and
• Paul Watts

Beilstein J. Org. Chem. 2016, 12, 1987–2004, doi:10.3762/bjoc.12.186

• principles of green chemistry [1][2] such as less hazardous chemical synthesis, efficient atom economy, reduction of waste produced, some alternative cleaner methods for the synthesis of azo dyes have been developed. These methods are however only representative of particular coupling agents and diazotized

• in a chemical synthesis, it is important to keep most factors constant especially those pertaining to the geometry of the reactor channel as this can affect the reaction output. Albeit comparable reaction conversions were attained from the two reactor systems investigated, it is worth determining the

Synthesis and NMR studies of malonyl-linked glycoconjugates of N-(2-aminoethyl)glycine. Building blocks for the construction of combinatorial glycopeptide libraries

• Markus Nörrlinger,
• Sven Hafner and
• Thomas Ziegler

Beilstein J. Org. Chem. 2016, 12, 1939–1948, doi:10.3762/bjoc.12.183

• saccharide synthesis makes it sometimes impossible to prepare a certain saccharide or glycoconjugate [9]. Therefore, gaining access to new glycoconjugates which are easily accessible by chemical synthesis and which are able to mimic the interaction between a specific protein and its natural oligosaccharide

• efficient chemical synthesis of a series of novel PNA-based glycopeptoids. We also studied the cis/trans rotamers of these glycopeptoids via temperature-dependent 1H NMR spectroscopy by determining the corresponding coalescence temperatures (Tc = 90–95 °C) and by calculating the specific rotation barrier

A flow reactor setup for photochemistry of biphasic gas/liquid reactions

• Josef Schachtner,
• Patrick Bayer and
• Axel Jacobi von Wangelin

Beilstein J. Org. Chem. 2016, 12, 1798–1811, doi:10.3762/bjoc.12.170

• to oxidation chemistry of utmost sustainability. Under irradiation in the presence of a sensitizer, singlet oxygen can easily be generated from the triplet ground state. Several applications of such photooxidations to chemical synthesis have been reported [71][72][73], in recent years most

Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides

• Mizuki Yamada,
• Mio Matsumura,
• Yuki Uchida,
• Masatoshi Kawahata,
• Yuki Murata,
• Naoki Kakusawa,
• Kentaro Yamaguchi and
• Shuji Yasuike

Beilstein J. Org. Chem. 2016, 12, 1309–1313, doi:10.3762/bjoc.12.123

• -triazoles (Bi), which could be employed as versatile building blocks in chemical synthesis [24]. One drawback of the Cu-catalyzed cycloaddition of alkynylbismuthanes is the requirement of alkyne derivatives based on the phenothiabismuthane 5,5-dioxide framework for stabilization. The utility of

Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines

• Eric Buchy,
• Branko Vukosavljevic,
• Maike Windbergs,
• Dunja Sobot,
• Camille Dejean,
• Simona Mura,
• Patrick Couvreur and
• Didier Desmaële

Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109

• , its coupling with gemcitabine and the Raman spectra of the deuterated GemSQ nanoassemblies, opening the way to perform intracellular imaging of squalenoyl nanomedicine (Figure 1). Results and Discussion Chemical synthesis of squalenic acid-d6 and GemSQ-d6 conjugate In a first approach we decided to

Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(−)-myrtenol nitrate

• Sean P. Bew,
• Glyn D. Hiatt-Gipson,
• Graham P. Mills and
• Claire E. Reeves

Beilstein J. Org. Chem. 2016, 12, 1081–1095, doi:10.3762/bjoc.12.103

• , reinforces the need for chemical synthesis studies on the formation of climate relevant organic nitrates [14]. Even though the atmospheric synthesis of structure diverse C5-IPNs, i.e., 4–10 is thought to be efficient, i.e., up to 15% yield [15] what is not currently fully understood is the mechanism or

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• isolated from Leptosphaeria maculans and named phomapyrone A, as well as from the mediterranean ascoglossan mollusc Ercolania funereal, described as cyercene [51]. Phomenin A displayed phytotoxicity at a concentration of 100 µg/mL. Chemical synthesis approaches enabled then to investigate many more α

• agronomically important pathogens, e.g., complete inhibition of Magnaporthe grisea and Phaeosphaeria nodorum at 67 µg/mL, and Botrytis cinerea was inhibited at 200 µg/mL. 2 Biosynthesis Even though the α-pyrones possessing interesting activities were in the focus of chemical synthesis approaches for a long time

A selective and mild glycosylation method of natural phenolic alcohols

• Mária Mastihubová and
• Monika Poláková

Beilstein J. Org. Chem. 2016, 12, 524–530, doi:10.3762/bjoc.12.51

• had to be optimized. The current paper deals with an efficient, safe and uniform chemical synthesis of various p-hydroxyarylalkyl glycosides, including compounds 1–3. Results and Discussion Preparation of aglycones The synthesis of the appropriate aglycones 6a–c was commenced from readily available

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

• Shino Manabe and
• Yukishige Ito

Beilstein J. Org. Chem. 2016, 12, 328–333, doi:10.3762/bjoc.12.35

• -containing lincosamide antibiotic [19]. Due to the limited availability of MSH from M. smegmatis cell culture (<1.5 mg of MSH from 1 L culture) [20], the chemical synthesis of MSH is highly desired. Bewley et al. and Lee and Rosazza independently reported the synthesis of MSH and determined the absolute

Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

• Tatjana Huber,
• Lara Weisheit and
• Thomas Magauer

Beilstein J. Org. Chem. 2015, 11, 2521–2539, doi:10.3762/bjoc.11.273

• Tatjana Huber Lara Weisheit Thomas Magauer Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstraße 5–13, 81377 Munich, Germany 10.3762/bjoc.11.273 Abstract This review describes strategies for the chemical synthesis of xenicane diterpenoids and structurally

Two strategies for the synthesis of the biologically important ATP analogue ApppI, at a multi-milligram scale

• Janne Weisell,
• Jouko Vepsäläinen and
• Petri A. Turhanen

Beilstein J. Org. Chem. 2015, 11, 2189–2193, doi:10.3762/bjoc.11.237

• the chemical synthesis of ApppI. One is the method Mönkkönen et al. [3] followed in their synthesis which has been first described by Eggerer and Lynen [5] and another method is the chemical synthesis of ApppI described by Vantourout et al. [6]. According to our earlier experiments following the

Design and synthesis of propellane derivatives and oxa-bowls via ring-rearrangement metathesis as a key step

• Sambasivarao Kotha and
• Rama Gunta

Beilstein J. Org. Chem. 2015, 11, 1727–1731, doi:10.3762/bjoc.11.188

• target molecule, eventually to arrive at simple starting materials by working in an opposite direction to a chemical synthesis. The ‘retrosynthetic analysis’ was first introduced by E. J. Corey and defined as “it is a problem solving technique for transforming the structure of a synthetic target molecule

• to a sequence of progressively simpler structures along a pathway which ultimately leads to a simple or commercially available starting materials for a chemical synthesis” [1] . Generally, this type of retrosynthetic analysis has been used to design [2][3][4][5][6] the target molecule. However, a

The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134

• incorporated analysis technique. As the safe use of organometallic reagents has emerged as a key facet of flow chemical synthesis [58], the ITC reported on the design and implementation of a dual injection loop system that could deliver solutions of organometallic reagents (i.e., LiHMDS or n-BuLi) as a pseudo

• chemistry is an increase in reproducibility this seems a rather negative trend. In 2012 researchers from AstraZeneca (Sweden) reported upon a scale-up campaign for their gastroesophageal reflux inhibitor programme. Specifically, flow chemical synthesis was used to efficiently and reliably provide sufficient

• in flow Another example in which flow chemical synthesis was used as the key step in an industrial setting was reported by scientists from Eli Lilly (USA) in 2012. An asymmetric high-pressure hydrogenation towards LY500307 (82) [75] was demonstrated (Scheme 14). As this campaign aimed to produce the

Azobenzene-based inhibitors of human carbonic anhydrase II

• Leander Simon Runtsch,
• David Michael Barber,
• Peter Mayer,
• Michael Groll,
• Dirk Trauner and
• Johannes Broichhagen

Beilstein J. Org. Chem. 2015, 11, 1129–1135, doi:10.3762/bjoc.11.127

• of the synthesized azobenzenes, we found that the electronic structure does not strongly affect inhibition. Taken together, all compounds are strong blockers of hCAII with Ki = 25–65 nM that are potentially photochromic and thus combine studies from chemical synthesis, crystallography and enzyme

Synthesis of photoresponsive cholesterol-based azobenzene organogels: dependence on different spacer lengths

• Yuchun Ren,
• Bin Wang and
• Xiuqing Zhang

Beilstein J. Org. Chem. 2015, 11, 1089–1095, doi:10.3762/bjoc.11.122

• Yuchun Ren Bin Wang Xiuqing Zhang Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province of China, China West Normal University, Nanchong 637009, China 10.3762/bjoc.11.122 Abstract A series of azobenzene–cholesterol organogel compounds (M0–M12) with different spacers were

• of China (2010008), Key Project of Natural Science of Sichuan Educational Department of China (12ZA175), Chemical synthesis and Pollution Control Key Laboratory of Sichuan Province of China (CSCP2013-2), and University research and launch projects of China West Normal University in 2014 (14C003).

N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity

• Agata Walczewska,
• Daria Grzywacz,
• Dorota Bednarczyk,
• Małgorzata Dawgul,
• Andrzej Nowacki,
• Wojciech Kamysz,
• Beata Liberek and
• Henryk Myszka

Beilstein J. Org. Chem. 2015, 11, 869–874, doi:10.3762/bjoc.11.97

• fact that thousands of homogeneous saponins have been characterized, new types of saponins are regularly isolated from nature and their biological activities are evaluated [7][8][9][10][11]. The yields of homogenous saponins isolated from natural sources are rather low. Therefore, chemical synthesis of

CO₂ Chemistry

• Thomas E. Müller and
• Walter Leitner

Beilstein J. Org. Chem. 2015, 11, 675–677, doi:10.3762/bjoc.11.76

• use of carbon dioxide as chemical feedstock. Notably, the use of CO2 for manufacturing materials and chemicals is still in its infancy. Carbon dioxide (CO2) has long stirred the fascination of chemists. A rich chemistry has evolved utilizing this molecule in chemical synthesis [4]. Hitherto the low

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

• Tor E. Kristensen

Beilstein J. Org. Chem. 2015, 11, 446–468, doi:10.3762/bjoc.11.51

• chemical synthesis. In principle, they can function as inexpensive, chiral and densely functionalized starting materials. On the other hand, the use of amino acid starting materials routinely necessitates protective group chemistry, and in reality, large-scale preparations of even the simplest side-chain

Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope

• Manuel Johannes,
• Maximilian Reindl,
• Bastian Gerlitzki,
• Edgar Schmitt and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15

• epitopes. Use of tetanus toxoid (TTox) and bovine serum albumin (BSA) as immunogenic carrier proteins allows application of these conjugates in immunization studies and diagnostic ELISA experiments [44]. Results and Discussion Chemical synthesis of the 4’-fluoro-TF neo-glycoconjugate The synthesis of the 4

NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A–T phosphoramidite building blocks

• Boris Schmidtgall,
• Claudia Höbartner and
• Christian Ducho

Beilstein J. Org. Chem. 2015, 11, 50–60, doi:10.3762/bjoc.11.8

• represents the first step towards a comprehensive set of 'dimeric' NAA-linked X–T phosphoramidites for the automated chemical synthesis of NAA-modified DNA oligonucleotides. Results and Discussion For the synthesis of target phosphoramidites 7, it was planned to employ a similar synthetic strategy as

Nucleic acid chemistry

• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2014, 10, 2928–2929, doi:10.3762/bjoc.10.311

• is of critical importance, carrying the genetic information for all living organisms. Only a few years later appeared the first reports on the chemical synthesis of oligonucleotides with a natural 3'-5' phosphodiester linker by Michelsen and Todd [2]. It took another two decades until the first step

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• ), and v) they are biodegradable and do not pollute the environment. Their main fields of application are: agriculture, food industry, biotechnology, pharmaceutical industry, chemical and biological analysis, chemical synthesis, catalysis, materials, cosmetic industry, environmental protection