Recent highlights in biosynthesis research using stable isotopes

• Jan Rinkel and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2015, 11, 2493–2508, doi:10.3762/bjoc.11.271

• products and are remarkably diverse in structure, bioactivity, and use. Prominent examples such as the antimalaria drug artemisinin (28) from Artemisia annua, ingenol (29) and its derivatives from Euphorbia ingens [56], or the anticancer drug paclitaxel (30) feature highly functionalized polycyclic carbon

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• bioavailability of the anticancer drug CPT. In a second step, interaction with mucus and the GI uptake of nanocapsules will be evaluated using artificial mucus model and in vivo animal studies. Scanning electron microphotographs of A) 6OCAPRO nanocapsules and B) CS-6OCAPRO nanocapsules. In vitro release profiles

Synthetic strategies for the fluorescent labeling of epichlorohydrin-branched cyclodextrin polymers

• Milo Malanga,
• Mihály Bálint,
• István Puskás,
• Kata Tuza,
• Tamás Sohajda,
• László Jicsinszky,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3007–3018, doi:10.3762/bjoc.10.319

• used for layer-by-layer film formation [12]. The synthesis and characterization of a nanosized quaternary ammonium β-CD polymer with high load capacity of the anticancer drug doxorubicin has been described as well as its application as drug delivery carriers across the blood–brain barrier [13]. The

Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier

• Kayoko Hayashida,
• Taishi Higashi,
• Daichi Kono,
• Keiichi Motoyama,
• Koki Wada and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292

• such as polyethylene glycol (PEG). On the other hand, PEGylated liposomes have been utilized as a representative anticancer drug carrier. However, little is known about the formation of CD PPRX with PEGylated liposome. In the present study, we first report the formation of CD PPRX with PEGylated

Linear-g-hyperbranched and cyclodextrin-based amphiphilic block copolymer as a multifunctional nanocarrier

• Yamei Zhao,
• Wei Tian,
• Guang Yang and
• Xiaodong Fan

Beilstein J. Org. Chem. 2014, 10, 2696–2703, doi:10.3762/bjoc.10.284

• MP1–MP3, lonidamine (LND) as a hydrophobic anticancer drug was selected (Supporting Information File 1, Scheme S4). The encapsulation efficiency (EE) and loading content (LC) of LND-loaded micelles (DLMP1, DLMP2, and DLMP3) are presented in Table 2. It was found that the EE and LC of DLMP3 were

Synthesis and characterization of a hyper-branched water-soluble β-cyclodextrin polymer

• Francesco Trotta,
• Fabrizio Caldera,
• Roberta Cavalli,
• Andrea Mele,
• Carlo Punta,
• Lucio Melone,
• Franca Castiglione,
• Barbara Rossi,
• Monica Ferro,
• Vincenza Crupi,
• Domenico Majolino,
• Valentina Venuti and
• Dominique Scalarone

Beilstein J. Org. Chem. 2014, 10, 2586–2593, doi:10.3762/bjoc.10.271

• at 450 nm, consistent with the formation of a SF/polymer complex. The solubilization capacity of the new branched β-CD polymer was also evaluated toward a very poor water soluble anticancer drug, i.e., paclitaxel, showing a great improvement in dispersion in water (data not shown). Conclusion A new

Design, automated synthesis and immunological evaluation of NOD2-ligand–antigen conjugates

• Marian M. J. H. P. Willems,
• Gijs G. Zom,
• Nico Meeuwenoord,
• Ferry A. Ossendorp,
• Herman S. Overkleeft,
• Gijsbert A. van der Marel,
• Jeroen D. C. Codée and
• Dmitri V. Filippov

Beilstein J. Org. Chem. 2014, 10, 1445–1453, doi:10.3762/bjoc.10.148

• respect to the second conjugation site, i.e., the isoglutamine residue, it has been reported that condensation of this acid with an unnatural amine does not affect the immunological properties of MDP [34]. A conjugate of the anticancer drug Paclitaxel with MDP has been described using this conjugation

Carbohydrate PEGylation, an approach to improve pharmacological potency

• M. Eugenia Giorgi,
• Rosalía Agusti and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 1433–1444, doi:10.3762/bjoc.10.147

• conjugated with both paclitaxel, a potent anticancer drug, and alendronate, a bone-targeting biphosphonate, in order to obtain strong bone tropism and fast drug release [12]. An enzymatic method using a microbial transglutaminase was described for PEGylation of human growth hormone [13]. Glycans have been

Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines

• Jian-bo Xie,
• Jian Luo,
• Timothy R. Winn,
• David B. Cordes and
• Guigen Li

Beilstein J. Org. Chem. 2014, 10, 746–751, doi:10.3762/bjoc.10.69

• Abstract A new approach to the anticancer drug Velcade was developed by performing asymmetric borylation of an imine anchored with a chiral N-phosphinyl auxiliary. Throughout the 7-step synthesis, especially in the imine’s synthesis and in the asymmetric borylation reactions, operations and work-up were

• reported so far [14][15][16][17][18][19][20]. Among the resulting products from the above methods, (R)-(1-amino-3-methylbutyl)boronic acid served as the key mechanism-based pharmacophore in the anticancer drug Velcade, which was the first FDA approved proteasome inhibitor, and has been in clinical use for

• different conditions. Moreover, the GAP auxiliaries have been proven to be easily deprotected under several conditions for re-use. Herein, we report the synthesis of the anticancer drug Velcade and its derivatives of chiral α-aminoboronic esters via GAP chemistry. Simple operations are needed during

Synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and its enantiomer: a non-proteinogenic amino acid segment of the linear pentapeptide microginin

• Rajendra S. Rohokale and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2014, 10, 667–671, doi:10.3762/bjoc.10.59

• anticancer drug taxol [9]. Due to the biological importance of (2S,3R)-AHDA, the enantioselective synthesis of its chiral core is a challenge task. This fact led to several approaches for the stereoselective synthesis of (2S,3R)-AHDA including (i) the enantioselective introduction of amino- and hydroxy

Modulating the activity of short arginine-tryptophan containing antibacterial peptides with N-terminal metallocenoyl groups

• H. Bauke Albada,
• Alina-Iulia Chiriac,
• Michaela Wenzel,
• Maya Penkova,
• Julia E. Bandow,
• Hans-Georg Sahl and
• Nils Metzler-Nolte

Beilstein J. Org. Chem. 2012, 8, 1753–1764, doi:10.3762/bjoc.8.200

• antibacterial and hemolysis studies. Discussion Ruthenium is one of the most promising metals in anticancer drug candidates [54][55][56][57], with two Ru-compounds even in clinical trials [58][59][60][61][62]. Surprisingly however, its potential in antibacterial research has not been explored so far. In this

Biosynthesis and function of secondary metabolites

• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2011, 7, 1620–1621, doi:10.3762/bjoc.7.190

• awarded the Nobel Prize in 1945. The discovery of new bioactive natural products is still a fascinating field in organic chemistry as demonstrated by the recent paradigms of the anticancer drug epothilon, the immunosuppressant rapamycin, or the proteasome inhibitor salinosporamide, to name but a few of

Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

• Lukas Hintermann,
• Mauro Perseghini and
• Antonio Togni

Beilstein J. Org. Chem. 2011, 7, 1421–1435, doi:10.3762/bjoc.7.166

• of a β-ketoester substructure (Figure 1c) [16]. Fluorinated agrochemicals and drugs are now produced industrially on a large scale by a range of methods, including reactions with notoriously reactive fluorine gas in the production of the anticancer drug fluorouracil (Figure 1d) [17]. However, many