Synthesis and characterization of water-soluble C₆₀–peptide conjugates

• Yue Ma,
• Lorenzo Persi and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2024, 20, 777–786, doi:10.3762/bjoc.20.71

• biomaterials since related in vitro bioassay systems require water solubility of the chemicals for testing. To overcome this important obstacle, over the past decades, a variety of water-soluble fullerenes have been reported [10]. General approaches towards enhancing the water solubility of fullerenes involve

Possible bi-stable structures of pyrenebutanoic acid-linked protein molecules adsorbed on graphene: theoretical study

• Yasuhiro Oishi,
• Motoharu Kitatani and
• Koichi Kusakabe

Beilstein J. Org. Chem. 2024, 20, 570–577, doi:10.3762/bjoc.20.49

• of molecules based on nanoscience can lead to a better understanding of the behavior of target biomaterials and improve the sensitivity of specific dynamical systems, such as biosensors. In this study, we investigate the behavior of proteins immobilized with linker molecules on graphene substrates

• reflected light of the probe light. For such laser-based biosensors, graphene's conductivity can provide a unique advantage. In fact, the conductivity of multilayered graphene is highly anisotropic. Therefore, the use of multilayer graphene avoids the burning of biomaterials by lasers irradiated from the

Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes

• Martina Mamone,
• Giuseppe Gentile,
• Jacopo Dosso,
• Maurizio Prato and
• Giacomo Filippini

Beilstein J. Org. Chem. 2023, 19, 575–581, doi:10.3762/bjoc.19.42

• Martina Mamone Giuseppe Gentile Jacopo Dosso Maurizio Prato Giacomo Filippini Department of Chemical and Pharmaceutical Sciences, INSTM UdR Trieste, University of Trieste, via Licio Giorgieri 1, 34127 Trieste, Italy Centre for Cooperative Research in Biomaterials (CIC BiomaGUNE), Basque Research

Recommendations for performing measurements of apparent equilibrium constants of enzyme-catalyzed reactions and for reporting the results of these measurements

• Robert N. Goldberg,
• Robert T. Giessmann,
• Peter J. Halling,
• Carsten Kettner and
• Hans V. Westerhoff

Beilstein J. Org. Chem. 2023, 19, 303–316, doi:10.3762/bjoc.19.26

• Robert N. Goldberg Robert T. Giessmann Peter J. Halling Carsten Kettner Hans V. Westerhoff Biosystems and Biomaterials Division, National Institute of Standards and Technology, Gaithersburg, Maryland, 20899, USA Institute for Globally Distributed Open Research and Education (IGDORE), Berlin

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

• Maxime Pypec,
• Laurent Jouffret,
• Claude Taillefumier and
• Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

• the crystal, reminiscent to that found in helical PPII-like structures. Interestingly, peptoids containing N-(methylamino)amides are soluble in water and are capable of forming hydrogen bonds, two interesting characteristics for designing peptidomimetic molecules or biomaterials. Additional efforts

Synthesis and bioactivity of pyrrole-conjugated phosphopeptides

• Qiuxin Zhang,
• Weiyi Tan and
• Bing Xu

Beilstein J. Org. Chem. 2022, 18, 159–166, doi:10.3762/bjoc.18.17

• controlling cell fate. Keywords: cells; enzyme; N-terminal; peptides; pyrroles; self-assembly; Introduction Biomacromolecular assemblies have received considerable attention recently in the field of biomaterials [1][2][3][4][5][6][7], among which peptides are of particular interest because of their unique

Polymer chemistry: fundamentals and applications

• Bernhard V. K. J. Schmidt

Beilstein J. Org. Chem. 2021, 17, 2922–2923, doi:10.3762/bjoc.17.200

• supramolecular chemistry for the assembly of polymer fibers and the synthesis of well-defined polysaccharides. In the direction of materials, cryogels and reinforced hydrogels are discussed, as well as 3D-printed poly(caprolactone) biomaterials. In addition, properties of thermoresponsive materials and self

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• Stimuli-responsive properties are often desirable for biomaterials used in drug-delivery applications. Here, we focus on temperature and solution pH response of cryogels as detailed below. 3.1. Temperature-responsive cryogels This is a property which can easily be applied and manipulated through careful

• , drug delivery and wound healing applications. It should be noted that whilst this section contains reference to tissue engineering, expansive detail on the subject matter is beyond the scope of this review. 5.1. 3D-Bioprinting of cryogels 3D-printing of biomaterials, or bioprinting, enables the control

• systems, progress can be made in achieving stable print structures for the ultra-high standards set by the human body. 5.2. Injectable cryogels Implantable biomaterials are proposed as a viable solution when dealing with issues relating to either the delivery or recruitment of cells. Currently the methods

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• Yudhi D. Kurniawan A'liyatur Rosyidah Research Center for Biomaterials, National Research and Innovation Agency, Cibinong, 16911, Indonesia Research Center for Biology, National Research and Innovation Agency, Cibinong, 16911, Indonesia 10.3762/bjoc.17.157 Abstract In recent years fifteen 5,6

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

• collapsed UCST polymer are promising and open new perspectives for the development of the next generation of smart, degradable biomaterials. In addition to the homopolymers mentioned above, more and more copolymers have been discovered, in which UCST behavior can be induced via hydrogen bonding

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

• Cansu Esen and
• Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

• ][10][11][12]. The potential of hydrogels is beyond biomaterials, currently these aqueous soft materials are prime candidates in agricultural delivery systems as well [13][14]. In the era of sustainability, utilization of sunlight is of great importance [15]. Metal-containing and mostly toxic and non

Enzyme-instructed morphological transition of the supramolecular assemblies of branched peptides

• Dongsik Yang,
• Hongjian He and
• Bing Xu

Beilstein J. Org. Chem. 2020, 16, 2709–2718, doi:10.3762/bjoc.16.221

• biomaterials, especially in cellular environment. Thus, we decided to further explore the molecular space and cell compatibility of enzyme-responsive branched peptides. Here, we report the use of an enzymatic reaction to cleave the branch off branched peptides for inducing the morphological transition of the

Palladium nanoparticles supported on chitin-based nanomaterials as heterogeneous catalysts for the Heck coupling reaction

• Tony Jin,
• Malickah Hicks,
• Davis Kurdyla,
• Sabahudin Hrapovic,
• Edmond Lam and
• Audrey Moores

Beilstein J. Org. Chem. 2020, 16, 2477–2483, doi:10.3762/bjoc.16.201

• abundant amine groups. While groups are starting to investigate the usage of chitin and chitosan-based supports for heterogeneous catalysis, there are still scarce investigations on using these biomaterials on the nanoscale, which can allow for higher accessibility of their functionalities towards better

• FTIR and PXRD showed little to no structural change to the biomaterials after metal deposition. Heck coupling results demonstrate the importance of using ChNCs as opposed to ChsNCs in order to control the redox chemistry of Pd, with full product yield in relatively mild conditions using PdNP@ChNC. TEM

Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio

• Dandan Li,
• Enjuro Harunari,
• Tao Zhou,
• Naoya Oku and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154

• and NMR analyses combined with state-of-the-art chemical approaches should unveil the detailed structure of PHAs and possibly offer a clue to alter the property of these promising biomaterials. Experimental General experimental procedures Optical rotations were recorded on a JASCO P-1030 polarimeter

Self-assembly behaviors of perylene- and naphthalene-crown macrocycle conjugates in aqueous medium

• Xin Shen,
• Bo Li,
• Tiezheng Pan,
• Jianfeng Wu,
• Yangxin Wang,
• Jie Shang,
• Yan Ge,
• Lin Jin and
• Zhenhui Qi

Beilstein J. Org. Chem. 2019, 15, 1203–1209, doi:10.3762/bjoc.15.117

• Xin Shen Bo Li Tiezheng Pan Jianfeng Wu Yangxin Wang Jie Shang Yan Ge Lin Jin Zhenhui Qi Sino-German Joint Research Lab for Space Biomaterials and Translational Technology, School of Life Sciences, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China Institute of Biomedical

A hemicryptophane with a triple-stranded helical structure

• Augustin Long,
• Olivier Perraud,
• Erwann Jeanneau,
• Christophe Aronica,
• Jean-Pierre Dutasta and
• Alexandre Martinez

Beilstein J. Org. Chem. 2018, 14, 1885–1889, doi:10.3762/bjoc.14.162

• a better understanding of the properties of this biological system and giving rise to numerous applications ranging from artificial collagenous biomaterials to peptides for therapeutic uses [3][4][5]. Recently, molecular cages presenting a triple helical structure have aroused a considerable

Superstructures with cyclodextrins: Chemistry and applications IV

• Gerhard Wenz

Beilstein J. Org. Chem. 2017, 13, 2157–2159, doi:10.3762/bjoc.13.215

• useful for transport into HeLa cells [18]. Due to their hydrophilicity, CD-derived superstructures have become more and more interesting for the construction of biomaterials. In particular, interactions between cellular components and CDs might lead to “greener medical applications” as summarized in this

Selective enzymatic esterification of lignin model compounds in the ball mill

• Ulla Weißbach,
• Saumya Dabral,
• Laure Konnert,
• Carsten Bolm and
• José G. Hernández

Beilstein J. Org. Chem. 2017, 13, 1788–1795, doi:10.3762/bjoc.13.173

• reactions involving reactants of poor solubility. This characteristic feature of mechanochemistry has proven fundamental while dealing with chemically induced cleavage of biomaterials such as lignin [11][12], cellulose [13][14][15] or chitin [16]. In regard to lignin chemistry, solution-based lignin

From chemical metabolism to life: the origin of the genetic coding process

• Antoine Danchin

Beilstein J. Org. Chem. 2017, 13, 1119–1135, doi:10.3762/bjoc.13.111

• provide an efficacious mechanism, but this involves surfaces in a straightforward way. Furthermore, it is still essential to associate prebiotic processes with selective steps that would retain only compounds that will evolve further into biomaterials. Surfaces, again, are a natural way forward. In

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

• Loïc Pantaine,
• Vincent Humblot,
• Vincent Coeffard and
• Anne Vallée

Beilstein J. Org. Chem. 2017, 13, 648–658, doi:10.3762/bjoc.13.64

• interest in the past decades because of their potential applications in various areas such as biomaterials, tissue engineering, biosensors and electronics [1][2][3]. The seminal work of Nuzzo and Allara on the adsorption of disulfides on gold surface has triggered numerous research activities in the

Versatile synthesis of end-reactive polyrotaxanes applicable to fabrication of supramolecular biomaterials

• Atsushi Tamura,
• Asato Tonegawa,
• Yoshinori Arisaka and
• Nobuhiko Yui

Beilstein J. Org. Chem. 2016, 12, 2883–2892, doi:10.3762/bjoc.12.287

• Atsushi Tamura Asato Tonegawa Yoshinori Arisaka Nobuhiko Yui Department of Organic Biomaterials, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda, Tokyo 101-0062, Japan 10.3762/bjoc.12.287 Abstract Cyclodextrin (CD)-threaded

• functional PRXs and can be applied to the fabrication of PRX-based supramolecular biomaterials. Keywords: azide group; biomaterials; click chemistry; cyclodextrin; polyrotaxane; Introduction Polyrotaxanes (PRXs) are a class of interlocked polymers that consist of an inclusion complex of cyclodextrins (CDs

• [2 + 3] dipolar cycloaddition reactions, or click reactions [10][11][12]. Indeed, our group has reported on PRXs bearing azide groups at the threading CDs for the introduction of ligands and fluorescent molecules in biomaterials applications [13][14]. PRXs bearing reactive azide or alkynyl groups at

Inhibition of peptide aggregation by means of enzymatic phosphorylation

• Kristin Folmert,
• Malgorzata Broncel,
• Hans v. Berlepsch,
• Christopher H. Ullrich,
• Mary-Ann Siegert and
• Beate Koksch

Beilstein J. Org. Chem. 2016, 12, 2462–2470, doi:10.3762/bjoc.12.240

• binding [43]. Additionally, phosphorylation may be found to direct desired behaviors in the currently intensively studied area of amyloid-based biomaterials. In this report we show the use of the negatively charged phosphate group to control the aggregation process. Using PKA and ATP (adenosine

• those influences is a major challenge to use enzymatic phosphorylation as a tool to control the aggregation process and for the development of new functional biomaterials based on amyloid morphologies. Experimental Peptide synthesis, purification and characterization Peptides were synthesized manually

Dinuclear thiazolylidene copper complex as highly active catalyst for azid–alkyne cycloadditions

• Anne L. Schöffler,
• Ata Makarem,
• Frank Rominger and
• Bernd F. Straub

Beilstein J. Org. Chem. 2016, 12, 1566–1572, doi:10.3762/bjoc.12.151

• conditions [4][5][6]. The CuAAC reaction has found broad application in the preparation of peptide-conjugates [7][8], multicomponent syntheses [9], preparation of hydrogels, microgels and nanogels [10], (anion) supramolecular chemistry [11][12], in medicinal chemistry [13], therapeutics, biomaterials and

Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides

• Madhuri Vangala and
• Ganesh P. Shinde

Beilstein J. Org. Chem. 2015, 11, 2289–2296, doi:10.3762/bjoc.11.249

• ) [4][5][6]. The strong affinity of the nitrogen in oxazoline towards metal makes the chiral derivatives excellent catalysts for asymmetrical transformations [7][8][9][10]. The amphiphilicity and biocompatibility of poly-2-substituted-2-oxazolines gained them recognition as biomaterials for polymer

Synthesis and evaluation of the biostability and cell compatibility of novel conjugates of nucleobase, peptidic epitope, and saccharide

• Dan Yuan,
• Xuewen Du,
• Junfeng Shi,
• Ning Zhou,
• Abdulgader Ahmed Baoum,
• Khalid Omar Al Footy,
• Khadija Omar Badahdah and
• Bing Xu

Beilstein J. Org. Chem. 2015, 11, 1352–1359, doi:10.3762/bjoc.11.145

• they constitute three key types of biomacromolecules–proteins, nucleic acids, and carbohydrates. Inspired by this molecular foundation resulted from evolution, we are developing biomaterials that consist of the covalent conjugates of these three classes of the basic building blocks of life. For example

• incorporation of peptidic epitopes into molecular conjugates that consist of a nucleobase, amino acids, and a saccharide for potentially developing new supramolecular biomaterials. Results and Discussion Molecular design Scheme 1 shows the chemical structures of the conjugates explored in this work. In the NAS

• ). Biostability The existence of proteolytic enzymes [39] in organism limits the applications of peptide-based biomaterials [40] in vivo. To evaluate the biostability of the conjugates 1–8, we incubated them with proteinase K (a powerful protease) in HEPES buffer at 37 °C for 24 h. As shown in Figure 3A