Design and synthesis of diazine-based panobinostat analogues for HDAC8 inhibition

• Sivaraman Balasubramaniam,
• Sajith Vijayan,
• Liam V. Goldman,
• Xavier A. May,
• Kyra Dodson,
• Sweta Adhikari,
• Fatima Rivas,
• Davita L. Watkins and
• Shana V. Stoddard

Beilstein J. Org. Chem. 2020, 16, 628–637, doi:10.3762/bjoc.16.59

• chemical synthesis details can be found in Supporting Information File 1. HDAC8 enzymatic activity assay A fluorogenic assay (BPS Bioscience, catalog # 50008) was performed to evaluate the inhibition potential of the designed inhibitors. The assay was carried out using the supplier’s instructions. TOI1

SnCl₄-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

• Kesatebrhan Haile Asressu and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2019, 15, 2990–2999, doi:10.3762/bjoc.15.295

• , De Meo and co-workers have reported the significant effect of O-substituents on atom C-7 on the reactivity of thiosialoside donors and on the anomeric stereoselectivity of chemical sialylations [21]. Thus, 2,7-anhydro-Neu5Ac can serve as a promising building block for the chemical synthesis of

• backbone of Neu5Ac. Thus, the aim of this study was to cleave the ring of the 2,7-anhydro derivatives with a choice of suitable Lewis acids as catalysts in order to utilize the acetolysis products as building blocks for the chemical synthesis of Neu5Ac-containing glycans. Results and Discussion It is known

Regioselectivity of glycosylation reactions of galactose acceptors: an experimental and theoretical study

• Enrique A. Del Vigo,
• Carlos A. Stortz and
• Carla Marino

Beilstein J. Org. Chem. 2019, 15, 2982–2989, doi:10.3762/bjoc.15.294

• amounts of carbohydrate-containing molecules. Due to the chemical nature of carbohydrates, with multiple possible linkage positions giving rise to different regioisomers, with two possible anomeric configurations, the chemical synthesis of complex oligosaccharides is difficult and a rather time-consuming

Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis

• Alonso Pardo-Vargas,
• Priya Bharate,
• Martina Delbianco and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2019, 15, 2936–2940, doi:10.3762/bjoc.15.288

• chemical synthesis of AM is an attractive alternative. AM polysaccharides as large as 92-mers as well as many shorter AM oligomers have been prepared by solution-phase synthesis [16][17][18][19][20]. These multi-step syntheses are challenging and time-consuming. AGA reduces time and effort to access

Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis

• David C. B. Siebert,
• Roman Sommer,
• Domen Pogorevc,
• Michael Hoffmann,
• Silke C. Wenzel,
• Rolf Müller and
• Alexander Titz

Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286

• sarcosine (Sar) and derivatives. Chemical synthesis of the native sequence ᴅ-Ala-Dha-Sar thioester required revision of the sequential peptide synthesis into a convergent strategy where the thioester with sarcosine was formed before coupling to the Dha-containing dipeptide. Keywords: antibiotic; argyrin

• G reveals that the antibiotic is deeply buried inside the protein’s binding pocket and only a few sites of the molecule can possibly be modified without introducing steric clash with the binding site. Besides the methoxytryptophan which has been addressed by chemical synthesis, one appealing

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

• Lorenzo Sansalone,
• Jun Zhao,
• Matthew T. Richers and
• Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

• designed our photoprobe to take full advantage of high thermodynamic stability of the cis configuration of 4FAB, thus our probe can be pre-set to ON or OFF and used for extended periods without change of function. Experimental Chemical synthesis Full experimental synthetic details can be found in

Synthetic terpenoids in the world of fragrances: Iso E Super^® is the showcase

• Alexey Stepanyuk and
• Andreas Kirschning

Beilstein J. Org. Chem. 2019, 15, 2590–2602, doi:10.3762/bjoc.15.252

• linked with a bouquet of methods to broaden the platform of molecules with favourable olfactory properties. These include chemical synthesis, microbiology and molecular biology associated with biotechnology and combinations based on these methods. Hence also the most recent developments in synthetic

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

• Debasish Pal and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2019, 15, 2563–2568, doi:10.3762/bjoc.15.249

• Debasish Pal Balaram Mukhopadhyay Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Kolkata, Mohanpur, Nadia 741246, India 10.3762/bjoc.15.249 Abstract The total chemical synthesis of the pentasaccharide repeating unit of the O-polysaccharide

Synthesis of novel sulfide-based cyclic peptidomimetic analogues to solonamides

• José Brango-Vanegas,
• Luan A. Martinho,
• Lucinda J. Bessa,
• Andreanne G. Vasconcelos,
• Alexandra Plácido,
• Alex L. Pereira,
• José R. S. A. Leite and
• Angelo H. L. Machado

Beilstein J. Org. Chem. 2019, 15, 2544–2551, doi:10.3762/bjoc.15.247

• represent standard deviations. Cell viability of human fibroblast exposed to compounds 9e (A) and 9g (B) for 24 and 48 hours. The values are expressed as mean ± SEM. ****p < 0.0001, **p < 0.005 and ***p < 0.001 versus DMEM control group. Macrocyclization strategy based on SN2’. Chemical synthesis of the MBH

• adducts 2 and their carboxylic acids 3. Chemical synthesis of the linear peptidomimetics 8. Macrocyclization strategy based on SN2’ reaction to affords the solonamide analogues 9 and their overall yields based on the initial resin’s molarity. Halos of hemolysis or inhibition of hemolysis of S. aureus ATCC

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

• Lei Zhang,
• Greta Linden and
• Olalla Vázquez

Beilstein J. Org. Chem. 2019, 15, 2500–2508, doi:10.3762/bjoc.15.243

• improved mismatch discrimination under physiological conditions than natural ones. Furthermore, PNAs have a straightforward chemical synthesis by Fmoc-based PNA solid-phase synthesis and remarkable stability against nuclease- and protease-mediated degradation [32][33]. In regard to all these beneficial

Current understanding and biotechnological application of the bacterial diterpene synthase CotB2

• Ronja Driller,
• Daniel Garbe,
• Norbert Mehlmer,
• Monika Fuchs,
• Keren Raz,
• Dan Thomas Major,
• Thomas Brück and
• Bernhard Loll

Beilstein J. Org. Chem. 2019, 15, 2355–2368, doi:10.3762/bjoc.15.228

• engineering to optimize product ratios or to alter the native product portfolio of the enzyme [9][26][27]. Furthermore, production by engineered microorganisms considerably reduces the cost compared to total chemical synthesis or extraction from natural sources, since the target compounds are produced from

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• increase the nucleophilic character, and stabilise the fulvene system (see dipolar forms in Scheme 1). Similar results have been observed by other groups [32][96][124][203]. Whilst many of the documented reactions focus on chemical synthesis and characterisation rather than applications, several

Synthesis, enantioseparation and photophysical properties of planar-chiral pillar[5]arene derivatives bearing fluorophore fragments

• Guojuan Li,
• Chunying Fan,
• Guo Cheng,
• Wanhua Wu and
• Cheng Yang

Beilstein J. Org. Chem. 2019, 15, 1601–1611, doi:10.3762/bjoc.15.164

• guest receptors [4][5]. Planar-chiral macrocyclic molecules are particularly interesting in the context of the host–guest complexation properties [6][7][8]. Pillararenes are typical examples of this type of compounds and have attracted considerable attention due to their facile chemical synthesis and

Mechanochemistry II

• José G. Hernández

Beilstein J. Org. Chem. 2019, 15, 1521–1522, doi:10.3762/bjoc.15.154

• strategy for the future of chemical synthesis. In fact, the potential of mechanochemistry in various domains of research, industry and in commercial entities has been recently recognized by the IUPAC after the inclusion of mechanochemistry among the ten chemical innovations that will change our world [2

Efficiency Eff_syn of complex syntheses as multicomponent reactions, its algorithm and calculations based on concrete criteria

• Heiner Eckert

Beilstein J. Org. Chem. 2019, 15, 1425–1433, doi:10.3762/bjoc.15.142

• . Comprehensive efforts are being undertaken in this field, including in large workshops, e.g., [1]. The efficiency of synthesis forms the core for the evaluation of innovations within synthesis chemistry [2][3][4][5][6] and is the indispensable requirement for a radical simplification of chemical synthesis [3

• ]. Concrete and reliable criteria must be available for this purpose, criteria that can be easily determined and measured, and which can also form the basis for an algorithm. The standard evaluation of a chemical synthesis is traditionally based on the overall yield yoa. This is the product of all sequential

• : novel MCR as key step in total synthesis of (+)-20S-camptothecin Another typical example for the simplification of a complex chemical synthesis [2][3] is the total synthesis of the extremely potent antitumor agent (+)-20S-camptothecin (3), which has been a highly effective agent for decades now. This

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

• chemical synthesis [7]. In fact, supramolecular technology has shown great importance in various kinds of functional materials, including natural protein complexes [8][9][10], hydrogels [11][12][13], carbon-based materials [14][15][16][17], self-healing materials [18][19][20][21][22][23], and composite

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

• Edorta Martínez de Marigorta,
• Jesús M. de Los Santos,
• Ana M. Ochoa de Retana,
• Javier Vicario and
• Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

• preparation of heterocyclic compounds. This is mainly due to the need to find new efficient methods in order to save raw materials and work time. Without doubt, multicomponent approaches in chemical synthesis take the advantage of those two saving features. This economical profit is especially interesting for

Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives

• Mikhail V. Makarov and
• Marie E. Migaud

Beilstein J. Org. Chem. 2019, 15, 401–430, doi:10.3762/bjoc.15.36

• reaction conditions for the glycosylation of nicotinamide. Historically, 2,3,5-tri-O-acyl-D-ribofuranosyl halides were used first (so called the halo route) and will be considered in the first place. 2.1.1. Glycosylation with 2,3,5-tri-O-acylribofuranosyl halides: The first works on the chemical synthesis

Synthesis of nonracemic hydroxyglutamic acids

• Dorota G. Piotrowska,
• Iwona E. Głowacka,
• Andrzej E. Wróblewski and
• Liwia Lubowiecka

Beilstein J. Org. Chem. 2019, 15, 236–255, doi:10.3762/bjoc.15.22

• dipeptide containing O-protected (2S,4R)-4-hydroxyglutamic acid 3 (Scheme 19). The cycloadduct 75 can be transformed in a similar manner into non-proteinogenic D-amino acids. From 4-hydroxyproline 4-Hydroxyproline could be used as a starting material in the chemical synthesis of 4-hydroxyglutamic acids when

Synthesis of α-D-GalpN₃-(1-3)-D-GalpN₃: α- and 3-O-selectivity using 3,4-diol acceptors

• Emil Glibstrup and
• Christian Marcus Pedersen

Beilstein J. Org. Chem. 2018, 14, 2805–2811, doi:10.3762/bjoc.14.258

• ] has triggered the interest of carbohydrate chemists since the early days of complex oligosaccharides synthesis. The structure of the pentasaccharide part of the Forssman antigen was resolved in the seventies [3][4] and soon thereafter Paulsen and Bünsch finished the chemical synthesis of the

Novel solid-phase strategy for the synthesis of ligand-targeted fluorescent-labelled chelating peptide conjugates as a theranostic tool for cancer

• Sagnik Sengupta,
• Mena Asha Krishnan,
• Premansh Dudhe,
• Ramesh B. Reddy,
• Bishnubasu Giri,
• Sudeshna Chattopadhyay and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2018, 14, 2665–2679, doi:10.3762/bjoc.14.244

• peptide synthesis (SPPS) as well as in chemical synthesis were purchased from Iris Biotech GmbH, Sigma-Aldrich, Merck and Spectrochem. Dry solvents were prepared by using drying agents and following usual methods. Peptide syntheses were carried out in sintered glass peptide vessels (Chemglass) by standard

Semi-synthesis and insecticidal activity of spinetoram J and its D-forosamine replacement analogues

• Kai Zhang,
• Jiarong Li,
• Honglin Liu,
• Haiyou Wang and
• Lamusi A

Beilstein J. Org. Chem. 2018, 14, 2321–2330, doi:10.3762/bjoc.14.207

• awarded the Presidential Green Chemistry Challenge Award in 1999 and 2008 [12]. At present, spinetoram is obtained from spinosyn J and spinosyn L by a chemical modification. However, the fermentation productivity of spinosyn J and spinosyn L is low. So a chemical synthesis of spinetoram would be helpful

Assessing the possibilities of designing a unified multistep continuous flow synthesis platform

• Mrityunjay K. Sharma,
• Roopashri B. Acharya,
• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2018, 14, 1917–1936, doi:10.3762/bjoc.14.166

• of flow chemistry which is not an easy task. The utilization of the same approach for the synthesis of a wide range of products is very challenging since each product in the chemical synthesis involves different synthesis procedures, different conditions, different phases and different isolation

• components can be used for different chemistries just by changing the flow rates or the operating conditions specific to the chemistry. The components will be arranged on a platform where the order of arrangement can be varied in terms of processing needed for chemical synthesis just by connecting the

Natural and redesigned wasp venom peptides with selective antitumoral activity

• Marcelo D. T. Torres,
• Gislaine P. Andrade,
• Roseli H. Sato,
• Cibele N. Pedron,
• Tania M. Manieri,
• Giselle Cerchiaro,
• Anderson O. Ribeiro,
• Cesar de la Fuente-Nunez and
• Vani X. Oliveira Jr.

Beilstein J. Org. Chem. 2018, 14, 1693–1703, doi:10.3762/bjoc.14.144

• investigated Dec-NH2, its LZ template and single/double substituted derivatives for their ability to selectively kill MCF-7 breast cancer cells. Results and Discussion Peptide design, chemical synthesis, purification and physicochemical analyses Dec-NH2 is a cationic α-helical antimicrobial and antiparasitic

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

• Yuichi Yoshimura,
• Hideaki Wakamatsu,
• Yoshihiro Natori,
• Yukako Saito and
• Noriaki Minakawa

Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137

• associated with the isolation of tumor-associated carbohydrate antigens from natural sources have impeded extensive research. Thus, the most promising approach to the supply of these antigens is to develop a suitable method for their chemical synthesis. To date, various glycosylation reactions capable of