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

• allows the conjugation of the cleavable side chain, and tyrosine provides additional aromatic–aromatic interactions, as shown in a recent cryo-EM structure (PDB: 6X5I) [41]. Based on the above rationale, the DEDDDLLIG sequences attach to the ε-amine of the lysine residue of the tetrapeptide Nap-ffky to

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

• Shahboz Yakubov and
• Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

• report [207], Lectka and co-workers achieved selective monofluorination of the benzylic C–H bonds of phenylalanine- and tyrosine-like residues in peptides under visible-light photosensitization. After screening a variety of sensitizers, such as 1,2,4,5-tetracyanobenzene, AQN, 1,4-dicyanobenzene, 1

Synthesis, docking study and biological evaluation of ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones as potential inhibitors of the mycobacterial galactan synthesis targeting the galactofuranosyltransferase GlfT2

• Marek Baráth,
• Jana Jakubčinová,
• Zuzana Konyariková,
• Stanislav Kozmon,
• Katarína Mikušová and
• Maroš Bella

Beilstein J. Org. Chem. 2020, 16, 1853–1862, doi:10.3762/bjoc.16.152

• share the common binding interactions described above. However, the 1bα binding mode slightly differed from the modes of the other compounds. In this case the PO4 and hydroxy group on C5 interacted with a metal ion and the hydroxy groups on C2 and C3 created the hydrogen bond with the tyrosine Y236

Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

• Dharmender Singh,
• Vipin Kumar and
• Virender Singh

Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146

• a variety of biological activities such as anticancer [24], inhibition of tyrosine phosphatase 1B, antioxidant properties, etc. [25][26][27]. Due to their numerous applications, they have found diverse uses such as thioindigo-like dyes, photoresponsive devices, and photoswitchable biomolecules [28

A dynamic combinatorial library for biomimetic recognition of dipeptides in water

• Florian Klepel and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2020, 16, 1588–1595, doi:10.3762/bjoc.16.131

• slightly alkaline buffer (pH 7.4). An excess of our target molecules, the simple dipeptides AA, FF and YY (Y for tyrosine), were added to one sample each. An additional sample without dipeptide addition served as reference. After several hours of stirring in an open vial the thiol functions of the

Oxime radicals: generation, properties and application in organic synthesis

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Alexander S. Budnikov and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

• oxidation of N-hydroxyguanidines and amidoximes [28], oxidation of tyrosine phenolic moiety in the presence of NO [29][30][31][32][33]. This review focuses on the synthetic use of oxime radicals. Most of the works on this topic have been published over the past ten years. In most cases, these are

Copper catalysis with redox-active ligands

• Agnideep Das,
• Yufeng Ren,
• Cheriehan Hessin and
• Marine Desage-El Murr

Beilstein J. Org. Chem. 2020, 16, 858–870, doi:10.3762/bjoc.16.77

• a neighboring tyrosine radical ligand for the shuttling of overall two protons and two electrons. This peculiar mechanism is enabled by transient storage of electronic density on the tyrosine ligands and perfectly illustrates the central role of ancillary pro-radical ligands in biological systems

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

• Man-Man Wang,
• Hao Huang,
• Lei Shu,
• Jian-Min Liu,
• Jian-Qiu Zhang,
• Yi-Le Yan and
• Da-Yong Zhang

Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25

• . Keywords: aryloxyacetic acid; herbicidal activity; 4-hydroxyphenylpyruvate dioxygenase; modification; synthesis; Introduction 4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD), which belongs to the family of non-heme FeII-containing enzymes, is a vital enzyme for tyrosine catabolism. This enzyme

Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2 + 2] cycloaddition and cycloreversion

• Sarah Kölsch,
• Heiko Ihmels,
• Jochen Mattay,
• Norbert Sewald and
• Brian O. Patrick

Beilstein J. Org. Chem. 2020, 16, 111–124, doi:10.3762/bjoc.16.13

• deactivation of a stilbene tyrosine kinase inhibitor by a [2 + 2] photocycloaddition [59]. As the quinolizinium ion has been established as a versatile platform for the development of DNA intercalators [60], we identified styryl-substituted quinolizinium derivatives as a promising basis for the search for

Installation of -SO₂F groups onto primary amides

• Jing Liu,
• Shi-Meng Wang,
• Njud S. Alharbi and
• Hua-Li Qin

Beilstein J. Org. Chem. 2019, 15, 1907–1912, doi:10.3762/bjoc.15.186

• binding sites (Figure 1) [20]. The smallest member of this family, methyl sulfonyl fluoride (MSF), is known as a selective and irreversible inhibitor of acetylcholinesterase (AChE) [21][22]. The sulfonyl fluoride inhibitors NSC 127755 was found for specifically modifying tyrosine-31 of DHFR in chicken

Molecular basis for the plasticity of aromatic prenyltransferases in hapalindole biosynthesis

• Takayoshi Awakawa and
• Ikuro Abe

Beilstein J. Org. Chem. 2019, 15, 1545–1551, doi:10.3762/bjoc.15.157

• , and the other PTases, but W119 is conserved or substituted with tyrosine among all of the aligned PTases (Figure 6). The aromatic amino acids around W119 are also important to support the aromatic substrates and cationic intermediates in the X-ray structural studies of CloQ and EpzP [28][30]. The

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

• András György Németh,
• György Miklós Keserű and
• Péter Ábrányi-Balogh

Beilstein J. Org. Chem. 2019, 15, 1523–1533, doi:10.3762/bjoc.15.155

• ), a new quinazolinone derivative in 40% yield (Scheme 6). Notably, these heterocycles are known for their use as antitumor [101], anticonvulsant [102] or epidermal growth factor receptor tyrosine kinase inhibitory agents [103], JNK inhibitors [104] or 5-HT3 antagonists [105]. Earlier, a one-pot

New sesquiterpenoids from the South China Sea soft corals Clavularia viridis and Lemnalia flava

• Qihao Wu,
• Yuan Gao,
• Meng-Meng Zhang,
• Li Sheng,
• Jia Li,
• Xu-Wen Li,
• Hong Wang and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2019, 15, 695–702, doi:10.3762/bjoc.15.64

• further support of the assigned structure for 6 (Figure 1). Thus, compound 6 was determined as a C-1 isomer of ent-1-hydroxyalloaromadendrene (6a), namely, claaromadendrene. In bioassays, all the isolated compounds were tested for protein tyrosine phosphase-1B (PTP1B) and NF-κB inhibitory activity. In the

Synthesis of the polyketide section of seragamide A and related cyclodepsipeptides via Negishi cross coupling

• Jan Hendrik Lang and
• Thomas Lindel

Beilstein J. Org. Chem. 2019, 15, 577–583, doi:10.3762/bjoc.15.53

• -bromoabrine unit of 1 could be replaced by phototryptophan [7], whereas photo β-phenylalanine [8] could replace the β-tyrosine moiety. For photoaffinity labelling studies with seragamides and geodiamolides, D-photophenylalanine could be incorporated. In this paper we describe, as the first step of such an

• A (2), we synthesized the tripeptide section. The assembly of the iodotyrosine moiety commenced with D-3-iodotyrosine that was obtained in 63% yield from D-tyrosine upon treatment with iodine (1 equiv, added via syringe pump over 90 min to avoid diiodination) in aqueous ammonia [43] (Scheme 4). This

New standards for collecting and fitting steady state kinetic data

• Kenneth A. Johnson

Beilstein J. Org. Chem. 2019, 15, 16–29, doi:10.3762/bjoc.15.2

• to determine when titrating with a known concentration of a substrate analog [13]. In addition, many proteins show a change in fluorescence (tyrosine and tryptophan residues) upon substrate binding, affording accurate measurements of the stoichiometry and dissociation constant for binding from an

Lectins of Mycobacterium tuberculosis – rarely studied proteins

• Katharina Kolbe,
• Sri Kumar Veleti,
• Norbert Reiling and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

• can be attributed to π-interactions with tyrosine residues located at the rim of the carbohydrate binding pocket (Figure 3) [64][75]. Importantly, adhesion of Mtb was observed to both mycobacterial- and host-specific carbohydrates indicating that cell surface-localized mycobacterial lectins may be

• was originally published in the thesis of K. Kolbe [12] and has been slightly modified for this article). Structure of FimH CRD with a docked azobenzene mannobioside showing the aromatic aglycon and the tyrosine residues, Y48 and Y137, of the protein in close proximity. The figure is a slightly

Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

• Akın Sağırlı and
• Yaşar Dürüst

Beilstein J. Org. Chem. 2018, 14, 3011–3017, doi:10.3762/bjoc.14.280

• bioactivities, such as anticancer [1], antimicrobial [2], antifungal [3], anti-inflammatory [4], tyrosine kinase inhibition [5] and histamine H3 antagonism properties [6]. In addition, these five-membered heterocycles were widely used as components of organic light emitting diodes (OLEDs), polymers, liquid

N-Acylated amino acid methyl esters from marine Roseobacter group bacteria

• Hilke Bruns,
• Lisa Ziesche,
• Nargis Khakin Taniwal,
• Laura Wolter,
• Thorsten Brinkhoff,
• Jennifer Herrmann,
• Rolf Müller and
• Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276

• Loktanella sp. D3 showed no antagonistic activity [29]. This observation fits well with the detection of antimicrobial or cytotoxic NAVME 9 and NABMEs 7 and 8 only in Roseovarius sp. D12_1.68. Bacteria are known to produce acylated amino acids, although the number reported so far is small, including tyrosine

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

• Nadia Bouzayani,
• Jamil Kraїem,
• Sylvain Marque,
• Yakdhane Kacem,
• Abel Carlin-Sinclair,
• Jérôme Marrot and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

• (3d), (L)-cysteine phenylhydrazide (3g), (L)-tyrosine phenylhydrazide (3j), (L)-alanine 4-chlorophenylhydrazide (3k), (L)-phenylglycine 4-chlorophenylhydrazide (3l) and (L)-phenylalanine 4-chlorophenylhydrazide (3m) were synthesized for the first time in this work. Verardo et al. [29] have shown that

Olefin metathesis catalysts embedded in β-barrel proteins: creating artificial metalloproteins for olefin metathesis

• Daniel F. Sauer,
• Johannes Schiffels,
• Takashi Hayashi,
• Ulrich Schwaneberg and
• Jun Okuda

Beilstein J. Org. Chem. 2018, 14, 2861–2871, doi:10.3762/bjoc.14.265

• movement of the catalyst with shorter spacer within the channel seems advantageous for the turnover. Additionally, a few potentially coordinating residues (glutamic acid and tyrosine) are further away from the active site when the shorter spacer is utilized [60]. Structural expansions of β-barrel proteins

Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles

• Takashi Go,
• Akane Morimatsu,
• Hiroaki Wasada,
• Genzoh Tanabe,
• Osamu Muraoka,
• Yoshiharu Sawada and
• Mitsuhiro Yoshimatsu

Beilstein J. Org. Chem. 2018, 14, 2722–2729, doi:10.3762/bjoc.14.250

• compounds operate by inhibiting proteins or enzymes that regulate cell cycles, including cyclin-dependent kinases [9], tyrosine kinase [10], glycogen-synthase kinase and mitochondrial malate dehydrogenase [11]. These interesting biological activities led us to develop one-pot sequential or cascade protocols

Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections

• Matthew B. Calvert,
• Varsha R. Jumde and
• Alexander Titz

Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239

• interact with the tyrosine gate formed by Tyr48 and Tyr137 [15][16], as well as form hydrogen bonds and electrostatic interactions with the Arg98/Glu50 salt bridge of the protein. Taking this coordination geometry into consideration for further ligand optimization, it was found important to focus on the

• aglycon part of the mannosides. The attachment of lipophilic aglycons to an α-linked mannose residue was identified to increase the binding potency tremendously due to the opening of a lipophilic cleft on FimH, the tyrosine gate [15]. Various alkyl mannosides 1 (Figure 1) were analyzed and n-heptyl

• mannoside (1b) revealed the highest potency, as a result of it having the optimal length to bind to the tyrosine gate. Lindhorst and co-workers have demonstrated that mannosides with an extended aromatic aglycon could further improve the interaction as shown for compounds 2 and 3. Their relative inhibitory

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• group report are scaffolds and moieties seen in typical medicinal chemistry syntheses. There are numerous examples of amino acid-derived substrates, either as the methoxybenzene electrophile (tyrosine type derivatives) or as the nucleophile (histidine and related structures such as the depicted triazole

Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester

• Takao Shoji,
• Hiroki Fukutomi,
• Yohei Okada and
• Kazuhiro Chiba

Beilstein J. Org. Chem. 2018, 14, 1946–1955, doi:10.3762/bjoc.14.169

• compatibility is of immense versatility since synthesized peptide fragments, which are cleaved from their supports thus freeing the C-terminus, could directly be conjugated to the 5’-terminus of oligonucleotides via tyrosine, serine, or threonine side chains. In order to demonstrate such a versatile conjugation