Search results

Search for "tyrosine" in Full Text gives 143 result(s) in Beilstein Journal of Organic Chemistry.

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

Graphical Abstract
  • . 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
PDF
Album
Supp Info
Full Research Paper
Published 19 Feb 2020

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

Graphical Abstract
  • 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
PDF
Album
Supp Info
Full Research Paper
Published 23 Jan 2020

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

Graphical Abstract
  • 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
PDF
Album
Supp Info
Letter
Published 09 Aug 2019

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

Graphical Abstract
  • , 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
PDF
Album
Review
Published 11 Jul 2019

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

Graphical Abstract
  • ), 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
PDF
Album
Supp Info
Full Research Paper
Published 10 Jul 2019

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

Graphical Abstract
  • 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
PDF
Album
Supp Info
Full Research Paper
Published 15 Mar 2019

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

Graphical Abstract
  • -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
PDF
Album
Supp Info
Full Research Paper
Published 28 Feb 2019

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

Graphical Abstract
  • 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
PDF
Album
Review
Published 02 Jan 2019

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

Graphical Abstract
  • 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
PDF
Album
Review
Published 02 Jan 2019

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

Graphical Abstract
  • 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
PDF
Album
Supp Info
Full Research Paper
Published 10 Dec 2018

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

Graphical Abstract
  • 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
PDF
Album
Supp Info
Full Research Paper
Published 03 Dec 2018

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

Graphical Abstract
  • (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
PDF
Album
Supp Info
Full Research Paper
Published 26 Nov 2018

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

Graphical Abstract
  • 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
PDF
Album
Review
Published 19 Nov 2018

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

Graphical Abstract
  • 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
PDF
Album
Supp Info
Full Research Paper
Published 29 Oct 2018

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

Graphical Abstract
  • 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
PDF
Album
Review
Published 11 Oct 2018

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

Graphical Abstract
  • 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
PDF
Album
Review
Published 03 Aug 2018

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

Graphical Abstract
  • 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
PDF
Album
Supp Info
Full Research Paper
Published 27 Jul 2018

Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH

  • Femke Beiroth,
  • Tomas Koudelka,
  • Thorsten Overath,
  • Stefan D. Knight,
  • Andreas Tholey and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163

Graphical Abstract
  • binding site, undergoing interactions with the protein surface, which add to affinity. Especially CH–π or π–π interactions of a sugar ligand with the side chains of Y48 and Y137, called the “tyrosine gate” [19][20], are known to considerably increase the affinity of a specific mannoside for FimH
  • force field and 30 different conformers of each ligand were docked into two different X-ray structures of FimH (for details see Supporting Information File 1). These two crystal structures differ in the conformation of the tyrosine gate, formed by Y48 and Y137 positioned at the entrance of the
  • alcohol as the simplest tyrosine mimic. Mass-spectrometric analysis indicated the desired crosslinked product as well as insertion into water in both cases (cf. Supporting Information File 1, Table S5). Hence, carbene formation upon irradiation of diazirine 3 was ensured and thus we continued further
PDF
Album
Supp Info
Full Research Paper
Published 24 Jul 2018

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

  • Fateh V. Singh,
  • Priyanka B. Kole,
  • Saeesh R. Mangaonkar and
  • Samata E. Shetgaonkar

Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152

Graphical Abstract
  • ) for spirocyclization of N-protected tyrosine 14 to spirolactone 16. The spirocyclization reaction was carried out in methanol using stoichiometric amounts of PIDA (15) and spirolactone 16 was isolated in 35% yield (Scheme 2). Probably, the cyclization reaction proceeded via dearomatizaion of phenolic
  • acid and 4-iodophenylacetic acid in two steps (Figure 2). Both polymer-supported reagents 17a and 17b were used in similar spirocyclizations of tyrosine 14. Both tyrosine 14a and N-protected tyrosine derivatives 14b,c were used as starting material and results of their spirolactonization are summarized
  • in Table 1 (Scheme 3). The spirolactonization products 16 were isolated in excellent yields when reactions were performed with substrates 14 (R = NH2) having free amino group (Table 1, entries 1 and 2). Notably, the poor yields were observed during the spirolactonization of N-protected tyrosine
PDF
Album
Review
Published 17 Jul 2018

Defining the hydrophobic interactions that drive competence stimulating peptide (CSP)-ComD binding in Streptococcus pneumoniae

  • Bimal Koirala,
  • Robert A. Hillman,
  • Erin K. Tiwold,
  • Michael A. Bertucci and
  • Yftah Tal-Gan

Beilstein J. Org. Chem. 2018, 14, 1769–1777, doi:10.3762/bjoc.14.151

Graphical Abstract
  • of the chain-length for effective binding, while the tyrosine substitution results suggest that the binding pockets within the ComD2 receptor cannot accommodate polar/electron-rich substituents. Structural analysis of CSP1 analogs Next, we wanted to assess the impact our modifications to the CSP1
PDF
Album
Supp Info
Full Research Paper
Published 16 Jul 2018

Novel unit B cryptophycin analogues as payloads for targeted therapy

  • Eduard Figueras,
  • Adina Borbély,
  • Mohamed Ismail,
  • Marcel Frese and
  • Norbert Sewald

Beilstein J. Org. Chem. 2018, 14, 1281–1286, doi:10.3762/bjoc.14.109

Graphical Abstract
  • cryptophycin analogues. The O-methyl group of the unit B D-tyrosine analogue was replaced by an O-(allyloxyethyl) moiety, an O-(hydroxyethyl) group, or an O-(((azidoethoxy)ethoxy)ethoyxethyl) substituent. While the former two maintain cytotoxicity in the subnanomolar range, the attachment of the triethylene
  • -tyrosine. Different chains for unit B have been investigated, albeit the elongation of the methoxy group is still unknown. Therefore, in the current study, we embarked on the synthesis of novel cryptophycin analogues containing different substituents at the phenolic hydroxy group of the unit B. We intended
  • preparation of the two different spacers that were later connected to the phenol. Starting from triethylene glycol (3) or 2-allyloxyethanol (7) tosylations and nucleophilic displacements by azide or iodide substitution provided 6 and 9 in good yields. O-Alkylation of Boc-protected 3-chlorinated D-tyrosine 10
PDF
Album
Supp Info
Full Research Paper
Published 01 Jun 2018

Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis

  • Dan Liu,
  • Ya-Li Guo,
  • Jin Qu and
  • Chi Zhang

Beilstein J. Org. Chem. 2018, 14, 1112–1119, doi:10.3762/bjoc.14.97

Graphical Abstract
  • moderate yield (Table 1, entries 3 and 4). Notably, it is unnecessary to protect the hydroxy group of serine, threonine, or tyrosine in advance in the synthesis of these four peptides. The presence of an unprotected hydroxy group does not affect the coupling efficiency, which is consistent with peptide
PDF
Album
Supp Info
Full Research Paper
Published 22 May 2018

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

Graphical Abstract
  • ., pentetreotide (DTPA-d-Phe-c[Cys-Phe-d-Trp-Lys-Thr-Cys]-Thr-ol) [71]. Epidermal growth factor (EGF): Epidermal growth factor receptor (EGFR) is a transmembrane protein belonging to the ErbB family of receptor tyrosine kinases which consists of 4 structurally-related members: EGFR/HER1 (ErbB-1), HER2/neu (ErbB-2
PDF
Album
Review
Published 26 Apr 2018

Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery

  • Sabine Schuster,
  • Beáta Biri-Kovács,
  • Bálint Szeder,
  • Viktor Farkas,
  • László Buday,
  • Zsuzsanna Szabó,
  • Gábor Halmos and
  • Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64

Graphical Abstract
  • macromolecules such as mRNA and DNA [10][11]. More precisely, anthracyclines act as topoisomerase II toxins inhibiting DNA transcription and replication. They stabilize a DNA topoisomerase-II intermediate in which the DNA strands are separated and a specific tyrosine residue of the topoisomerase II is covalently
  • linked to the DNA by formation of a tyrosine phosphodiester [10][11][12]. Moreover, anthracyclines provide a beneficial auto-fluorescence allowing the performance of fluorescence based studies like confocal laser scanning microscopy (CLSM) and fluorescence-activated cell sorting (FACS) to investigate the
PDF
Album
Supp Info
Full Research Paper
Published 04 Apr 2018

Mannich base-connected syntheses mediated by ortho-quinone methides

  • Petra Barta,
  • Ferenc Fülöp and
  • István Szatmári

Beilstein J. Org. Chem. 2018, 14, 560–575, doi:10.3762/bjoc.14.43

Graphical Abstract
  • such intermediates. By selecting the appropriate reaction conditions (various pH and temperatures), they were able to alkylate free amino acids, e.g., glycine (Gly), L-serine (Ser), L-cysteine (Cys), L-lysine (Lys), L-tyrosine (Tyr) and glutathione (Glu) in aqueous solution to isolate 55 (Scheme 8
PDF
Album
Review
Published 06 Mar 2018
Other Beilstein-Institut Open Science Activities