An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• aqueous solution is probably well recognized in the literature. Less corrosive and toxic effects and the lack of dangerous vapors make it safe to handle under normal conditions. MSA as a biodegradable chemical is decomposed within 28 days by living organisms and is part of the natural sulfur cycle. During

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

• . The general architecture of PDCs consists of three building blocks: the tumor-homing peptide, the cytotoxic agent and the biodegradable connecting linker. The aim of the current review is to provide a spherical perspective on the basic principles governing PDCs, as also the methodology to construct

Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"

• Karolina Tiara,
• Mykhaylo A. Potopnyk and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2018, 14, 634–641, doi:10.3762/bjoc.14.50

• ] and aza-crown [17][18] derivatives, macrocyclic dilactams [19][20], and ureas [21], were prepared in our laboratory. Sucrose was also used by other groups as a precursor for the preparation of biodegradable polymers [22][23][24] and polymeric nanoparticles [25]. On the other hand, sucrose derivatives

Stimuli-responsive oligonucleotides in prodrug-based approaches for gene silencing

• Françoise Debart,
• Christelle Dupouy and
• Jean-Jacques Vasseur

Beilstein J. Org. Chem. 2018, 14, 436–469, doi:10.3762/bjoc.14.32

• nucleic acids (PNAs), a lipophilic triphenylphosphonium (TPP) cation was attached to the N-terminal extremity of a PNA through a biodegradable carbamate linker containing a disulfide bridge (Scheme 4B) [20]. It was shown that such PNA conjugates entered cells rapidly and efficiently. Furthermore, a 16-mer

• . Therefore, the biodegradable modification present in the prodrug could not be removed in extracellular media but only inside the cells. Two approaches have been reported using reductases or carboxyesterases to trigger transformation of ON prodrugs in native ONs. Although a post-synthesis introduction of the

• methods led to ON prodrugs of therapeutic interest in the antisense approach. A similar conclusion can be drawn from Lönnberg's work reported in 2005 that described the synthesis of homothymidylates and phosphorothioate analogs protected by the biodegradable 2,2-bis(ethoxycarbonyl)-3-(pivaloyloxy)propyl

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• environmental reasons. These issues also led to the quest for biodegradable MOFs, the first being prepared in 2010 by Miller et al. [77]. Another family of MOFs, ZIFs (zeolitic imidazolate frameworks), that involves organic imidazoles as linkers, has been explored for medicinal purposes as a result of the

One-pot synthesis of block-copolyrotaxanes through controlled rotaxa-polymerization

• Jessica Hilschmann,
• Gerhard Wenz and
• Gergely Kali

Beilstein J. Org. Chem. 2017, 13, 1310–1315, doi:10.3762/bjoc.13.127

• properties [6][11][12][13]. One of the most important class of important macrocycles, applied in polyrotaxane chemistry, are cyclodextrins (CDs) because they are nontoxic, biodegradable and available in industrial scale. Furthermore, CDs can be simply functionalized by modification of the hydroxy groups [14

Kinetic analysis of mechanoradical formation during the mechanolysis of dextran and glycogen

• Naoki Doi,
• Yasushi Sasai,
• Yukinori Yamauchi,
• Tetsuo Adachi,
• Masayuki Kuzuya and
• Shin-ichi Kondo

Beilstein J. Org. Chem. 2017, 13, 1174–1183, doi:10.3762/bjoc.13.116

• initiate the polymerization is frequently used to synthesize such a graft polymer [7]. Dextran (Dx), a biodegradable polysaccharide, has been utilized as a graft copolymer backbone. The glycosidic linkages between the α-glucose units of Dx synthesized from Leuconostoc mesenteroides are composed of

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

• Adrián A. Heredia and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2017, 13, 910–918, doi:10.3762/bjoc.13.92

• with DMF and PEG 200, we chose PEG 200 as the solvent for subsequent reactions, which is a non-toxic and inexpensive biodegradable material also used as a sustainable and alternative solvent due to its reusability [39]. Table 2 summarizes the results for the screening and concentration of the base used

Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

• Cristian Peptu,
• Mihaela Balan-Porcarasu,
• Alena Šišková,
• Ľudovít Škultéty and
• Jaroslav Mosnáček

Beilstein J. Org. Chem. 2017, 13, 779–792, doi:10.3762/bjoc.13.77

• Virology, Biomedical Research Center Slovak Academy of Sciences, Dúbravská cesta 9, 84541 Bratislava, Slovakia 10.3762/bjoc.13.77 Abstract Biodegradable oligolactide derivatives based on α-, β- and γ-cyclodextrins (CDs) were synthesized by a green procedure in which CDs play the role of both the initiator

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

Regulation of integrin and growth factor signaling in biomaterials for osteodifferentiation

• Qiang Wei,
• Theresa L. M. Pohl,
• Anja Seckinger,
• Joachim P. Spatz and
• Elisabetta A. Cavalcanti-Adam

Beilstein J. Org. Chem. 2015, 11, 773–783, doi:10.3762/bjoc.11.87

• ); be timed biodegradable; neither cause acute nor chronic inflammation; be easily stored and handled (sterilized); and the last be cost-effective [75][80]. The present delivery systems and methods have been systematically reviewed in recent literature [8][9][81]. In brief, growth factors in living

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

• , making the crystalline hydrochlorides unavailable from MeSO3H medium, thereby complicating the isolation and purification process due to the poor crystallinity of methanesulfonate salts, which in fact, quite frequently are ionic liquids. On the positive side, MeSO3H is biodegradable. In addition to the

Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers

• Thorbjørn Terndrup Nielsen,
• Catherine Amiel,
• Laurent Duroux,
• Kim Lambertsen Larsen,
• Lars Wagner Städe,
• Reinhard Wimmer and
• Véronique Wintgens

Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14

• to dextran backbones. The CPT was bound to the dextran by a cleavable ester linkage that should be biodegradable in vivo. It is demonstrated how the binding with β-CD polymers is affected by the number of CPT units on the polymer backbone and how this association can lead to novel nanoparticles in

Modification of physical properties of poly(L-lactic acid) by addition of methyl-β-cyclodextrin

• Toshiyuki Suzuki,
• Ayaka Ei,
• Yoshihisa Takada,
• Hiroki Uehara,
• Takeshi Yamanobe and
• Keiko Takahashi

Beilstein J. Org. Chem. 2014, 10, 2997–3006, doi:10.3762/bjoc.10.318

• Polytechnic University, 1583 Iiyama, Atsugi 243-0297, Japan; Fax +81-46-242-3000 10.3762/bjoc.10.318 Abstract Poly(L-lactic acid) (PLLA) is a biodegradable plastic and one of the most famous plastics made from biobased materials. However, its physical strength is insufficient compared to general-purpose

• PLLA and enhanced the drawability. Keywords: crystallinity; DSC; methyl-β-cyclodextrin; poly(L-lactic acid); Raman spectroscopy; Introduction Poly(L-lactic acid) (PLLA) has attracted attention because it is a biodegradable polymer derived from carbon-neutral resources. However, its melting point (Tm

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

• thus shown that the CD complexation allows an easy storage, a decrease of the environment toxicity without a significant decrease of the anticholinergic activity. Carbamate insecticides are less damaging for the environment, more biodegradable and less toxic for humans. However, insects become

An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards ‘clickable’ biodegradable polylactide

• Quanxuan Zhang,
• Hong Ren and
• Gregory L. Baker

Beilstein J. Org. Chem. 2014, 10, 1365–1371, doi:10.3762/bjoc.10.139

• family of water-soluble and temperature responsive biodegradable PLA material with tunable lower critical solution temperature (LCST) in a range from 25 to 65 °C was obtained after ‘click’ grafting with a mixture of alkyl and PEG azides. Starting from the same precursor 1 [18], Yu and coworkers have

Nonanebis(peroxoic acid): a stable peracid for oxidative bromination of aminoanthracene-9,10-dione

• Vilas Venunath Patil and
• Ganapati Subray Shankarling

Beilstein J. Org. Chem. 2014, 10, 921–928, doi:10.3762/bjoc.10.90

• important advantage is that it is stable at room temperature. Thus it can be a good alternative for the conventional peracids. In our previous work [11] (Scheme 1), we reported the use of biodegradable deep eutectic mixtures as an alternative solvent to conventional solvents. The reaction selectively gives

Flow synthesis of phenylserine using threonine aldolase immobilized on Eupergit support

• Jagdish D. Tibhe,
• Hui Fu,
• Timothy Noël,
• Qi Wang,
• Jan Meuldijk and
• Volker Hessel

Beilstein J. Org. Chem. 2013, 9, 2168–2179, doi:10.3762/bjoc.9.254

• esterification [27], oxidation and reduction [28], C–C bond formation [29], and polymerization [30]. Recent advancements in the field of enzymatic microreactors include the use of alginate/protamine/silica hybrid capsules with ultrathin membranes [31], monolithic enzyme microreactors [29][32], and biodegradable

A³-Coupling catalyzed by robust Au nanoparticles covalently bonded to HS-functionalized cellulose nanocrystalline films

• Jian-Lin Huang,
• Derek G. Gray and
• Chao-Jun Li

Beilstein J. Org. Chem. 2013, 9, 1388–1396, doi:10.3762/bjoc.9.155

• to their renewable, environmentally benign, naturally abundant, biodegradable and biocompatible nature, as well as their excellent mechanical properties and anticipated low cost [24][25][26]. CNCs are obtained from semicrystalline cellulose derived from wood fibers and plants. Potential applications

C–C Bond formation catalyzed by natural gelatin and collagen proteins

• Dennis Kühbeck,
• Basab Bijayi Dhar,
• Eva-Maria Schön,
• Carlos Cativiela,
• Vicente Gotor-Fernández and
• David Díaz Díaz

Beilstein J. Org. Chem. 2013, 9, 1111–1118, doi:10.3762/bjoc.9.123

• occurring structural protein in animal bones, skin and connective tissue (ca. one-third of the total protein mass in the body). Its low production cost and nontoxic, edible and biodegradable properties have made gelatin a common ingredient in food, pharmaceutical, cosmetic and photographic industries, among

The conjugation of nonsteroidal anti-inflammatory drugs (NSAID) to small peptides for generating multifunctional supramolecular nanofibers/hydrogels

• Jiayang Li,
• Yi Kuang,
• Junfeng Shi,
• Yuan Gao,
• Jie Zhou and
• Bing Xu

Beilstein J. Org. Chem. 2013, 9, 908–917, doi:10.3762/bjoc.9.104

• frequently served as scaffolds for tissue engineering and as carriers for drug delivery [1][2][3][4]. In the applications of drug delivery, it is common to use hydrogels made of biodegradable polymers to encapsulate therapeutic agents for controlled release of drugs by adjusting the pore sizes and

• inherently easily biodegradable. To meet the prerequisites for self-delivery systems, besides biodegradability, the hydrogelators should preserve the pharmacological efficacy of the therapeutic building blocks, any side effects should be minimized and the biocompatibility maximized. Therefore, a convenient

Mechanochemistry assisted asymmetric organocatalysis: A sustainable approach

• Pankaj Chauhan and
• Swapandeep Singh Chimni

Beilstein J. Org. Chem. 2012, 8, 2132–2141, doi:10.3762/bjoc.8.240

• energy [1][2][3][4]. These requirements are fulfilled by preventing or minimizing the use of volatile and toxic solvents and reagents, minimizing chemical wastage, development of atom-economical processes and recyclable supported catalyst that are less toxic, biodegradable and can be used at low loading

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• biodegradable material with negligible toxicity on cell cultures and are well-tolerated after injection in mice. Cyclodextrin-based nanosponges can form complexes with different types of lipophilic or hydrophilic molecules. The release of the entrapped molecules can be varied by modifying the structure to

Preparation of mixed trialkyl alkylcarbonate derivatives of etidronic acid via an unusual route

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

Beilstein J. Org. Chem. 2012, 8, 2019–2024, doi:10.3762/bjoc.8.228

• as biodegradable prodrugs of etidronate [11]. Previously, we also synthesized the first phosphorous end-modified alkyl carbonate derivative of HEBPA by a surprising route [18]. According to a SciFinder search, this is the only reported phosphorous end-modified BP carbonate derivative in the

• biodegradable derivatives of BPs. One rather straightforward way to improve the lipophilicity of these compounds is to prepare alkyl carbonate derivatives of BPs. Alkyl carbonate derivatives of phenol and naphthols have been reported to undergo chemical and enzymatic hydrolysis [21][22] and so they have been

Superstructures with cyclodextrins: Chemistry and applications

• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 1303–1304, doi:10.3762/bjoc.8.148

• macrocyclic cucurbiturils, CDs show a better solubility in water. On top of that, they are also biodegradable. Considering the importance of CDs as demonstrated above, we felt encouraged to summarize some of the latest results achieved in CD research. Contributions from leading research groups dealing with