Search results

Search for "N-terminal" in Full Text gives 104 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

  • Jens Frackenpohl,
  • David M. Barber,
  • Guido Bojack,
  • Birgit Bollenbach-Wahl,
  • Ralf Braun,
  • Rahel Getachew,
  • Sabine Hohmann,
  • Kwang-Yoon Ko,
  • Karoline Kurowski,
  • Bernd Laber,
  • Rebecca L. Mattison,
  • Thomas Müller,
  • Anna M. Reingruber,
  • Dirk Schmutzler and
  • Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

Graphical Abstract
  • (SORHA), Triticum aestivum (TRZAS), and Zea mays (ZEAMX). LpFAT A expression and purification: The fat a03 gene from Lemna paucicostata, in which the N-terminal amino acids representing the chloroplast transit peptide were replaced by an N-terminal 6xHis-tag, was cloned into a pET24 vector [3]. The LpFAT
PDF
Album
Supp Info
Full Research Paper
Published 01 Mar 2024

Elucidating the glycan-binding specificity and structure of Cucumis melo agglutinin, a new R-type lectin

  • Jon Lundstrøm,
  • Emilie Gillon,
  • Valérie Chazalet,
  • Nicole Kerekes,
  • Antonio Di Maio,
  • Ten Feizi,
  • Yan Liu,
  • Annabelle Varrot and
  • Daniel Bojar

Beilstein J. Org. Chem. 2024, 20, 306–320, doi:10.3762/bjoc.20.31

Graphical Abstract
  • confirmed and quantified this binding specificity in solution. Finally, we solved the high-resolution structure of the CMA1 N-terminal domain using X-ray crystallography, supporting our functional findings at the molecular level. Our study provides a comprehensive understanding of CMA1, laying the
  • aligned the individual units of the tandem repeat CBM13 domains, indicated by the N-terminal (34-158) and C-terminal units (162-286) and compared those to the domains of ricin (Figure 1b). R-type lectins have a characteristic Q-x-W structural motif close to their binding site, which is highly conserved
  • around W63 for the N-terminal domain and F273 for the C-terminal domain of CMA1. As binding specificities of melon lectins in general (beyond chitooligosaccharides), and CMA1 in particular, are still unknown, we set out to measure, quantify, and understand the glycan-binding properties of CMA1 in depth
PDF
Album
Supp Info
Full Research Paper
Published 19 Feb 2024

Functions of enzyme domains in 2-methylisoborneol biosynthesis and enzymatic synthesis of non-natural analogs

  • Binbin Gu,
  • Lin-Fu Liang and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1452–1459, doi:10.3762/bjoc.19.104

Graphical Abstract
  • studied. Several 2-methylisoborneol synthases have a proline-rich N-terminal domain of unknown function. The results presented here demonstrate that this domain leads to a reduced enzyme activity, in addition to its ability to increase long-term solubility of the protein. Furthermore, the substrate scope
  • versions of 2MIBSs exhibit a proline-rich N-terminal domain of unknown function that appears disordered in the crystal structure [28]. As a first aspect of this study, we have investigated the possible function of this N-terminal domain. 2MIBS is known to form several methylated monoterpenes as side
  • changed alkylation pattern. Results and Discussion Function of the proline-rich N-terminal domain of 2MIBS S. coelicolor 2MIBS was selected to investigate the function of the proline-rich N-terminal domain (hereafter termed A domain, the C-terminal domain is named as domain B). Based on a sequence
PDF
Album
Supp Info
Letter
Published 22 Sep 2023

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

  • Cécile Alleman,
  • Charlène Gadais,
  • Laurent Legentil and
  • François-Hugues Porée

Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23

Graphical Abstract
PDF
Album
Review
Published 03 Mar 2023

Navigating and expanding the roadmap of natural product genome mining tools

  • Friederike Biermann,
  • Sebastian L. Wenski and
  • Eric J. N. Helfrich

Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178

Graphical Abstract
  • minimally harbors three core domains, responsible for the activation and loading, tethering, and condensation of building blocks and intermediates. The biosynthesis is directional and starts at the N-terminal module with the activation and loading of the first building block onto the assembly line (Figure
PDF
Album
Perspective
Published 06 Dec 2022

On drug discovery against infectious diseases and academic medicinal chemistry contributions

  • Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

Graphical Abstract
  • -bearing substances, endowed with an antibacterial effect [58]. However, this compound was originally patented for a fungicide effect [59] and then found to also inhibit mammalian c-Jun N-terminal kinase [60]. Unsurprisingly, it was also reported in 2022 as a covalent inhibitor for the SARS-CoV-2 main
PDF
Album
Perspective
Published 29 Sep 2022

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

  • Michael Keppler,
  • Sandra Moser,
  • Henning J. Jessen,
  • Christoph Held and
  • Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

Graphical Abstract
  • soluble enzymes and could be easily purified via Ni-NTA affinity chromatography using N-terminal His-tags, the PPK1 enzymes required an N-terminal maltose binding protein (MBP-tag) to improve solubility [46][47]. Trials to cleave the MBP-tag were unsuccessful and resulted in inactive protein aggregates
PDF
Album
Supp Info
Full Research Paper
Published 20 Sep 2022

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

  • Jamshid Amiri Moghaddam,
  • Huijuan Guo,
  • Karsten Willing,
  • Thomas Wichard and
  • Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

Graphical Abstract
  • and amplified sequences were then cloned into an expression pET28 plasmid containing an N-terminal 6-histidine tag sequence. Heterologous production of enzymes was achieved in E. coli BL21 and western blot analysis indicated the accumulation of His-tagged UbiA-297 (35 kD) within concentrated cell
PDF
Album
Supp Info
Full Research Paper
Published 22 Jun 2022

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

Graphical Abstract
  • cells by a naphthyl-capped phosphopeptide (Nap-ffpy, 1), we conjugated the heteroaromatic dipyrrole or tripyrrole motif at the N-terminal of short peptides containing phosphotyrosine or phosphoserine and examined the bioactivity of the resulting phosphopeptides (2–10). Although most of the
  • of 1. These results suggest that a heteroaromatic motif at the N-terminal of peptides likely disfavors the formation of extensive nanofibers or morphological changes during enzymatic self-assembly, thus provide useful insights for the development of phosphopeptides as substrates of phosphatases for
  • 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
PDF
Album
Supp Info
Full Research Paper
Published 31 Jan 2022

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

  • Hendrik Gruß,
  • Rebecca C. Feiner,
  • Ridhiwan Mseya,
  • David C. Schröder,
  • Michał Jewgiński,
  • Kristian M. Müller,
  • Rafał Latajka,
  • Antoine Marion and
  • Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

Graphical Abstract
  • phthaloyl-protected N-terminal alanine was also used for macrocyclisation in peptide stapling [51][52]. Besides addressing the indole C2, the regioselective enzymatic halogenation at C5, C6, or C7 using FAD-dependent tryptophan halogenases opens a broad area of Pd-catalysed late-stage diversifications [53
  • partner β-catenin. The N-terminal FITC-labelled RCM-stapled peptide fStAx-3 was synthesised as tracer for this study and its dissociation constant was determined to be 63 ± 6 nM in a direct fluorescence polarisation assay, which is in agreement with previously reported data [77]. Noteworthy, the isomer
PDF
Album
Supp Info
Full Research Paper
Published 03 Jan 2022

First total synthesis of hoshinoamide A

  • Haipin Zhou,
  • Zihan Rui,
  • Yiming Yang,
  • Shengtao Xu,
  • Yutian Shao and
  • Long Liu

Beilstein J. Org. Chem. 2021, 17, 2924–2931, doi:10.3762/bjoc.17.201

Graphical Abstract
  • -Val5 and N-Me-ᴅ/ʟ-Phe2. Hoshinoamide C includes two N-methyl amino acids: N-Me-ᴅ-Phe2 and N-Me-ᴅ-IIe5. The C-terminal Pro is functionalized as methyl ester, while the N-terminal polypeptide is linked to the long alkyl chain amino acid Aha8/Ana8/Ama7 and p-hydroxybenzoic acid Hba9/Hba8. Hoshinoamides
PDF
Album
Supp Info
Letter
Published 15 Dec 2021

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

  • Nikita Brodyagin,
  • Martins Katkevics,
  • Venubabu Kotikam,
  • Christopher A. Ryan and
  • Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Graphical Abstract
PDF
Album
Review
Published 19 Jul 2021

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

  • Santiago Ramos-Carreño,
  • Ivone Giffard-Mena,
  • Jose N. Zamudio-Ocadiz,
  • Alfredo Nuñez-Rivera,
  • Ricardo Valencia-Yañez,
  • Jaime Ruiz-Garcia,
  • Maria Teresa Viana and
  • Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

Graphical Abstract
  • -dsRNA to form procapsids and CP-RNA complexes [42]. The dsRNA negative charges can be neutralized by the positive N-terminal protein in these procapsids [42]. However, procapsids are not suitable for any treatment because they do not efficiently protect their cargo. The dsRNA in the procapsids may be
PDF
Album
Supp Info
Full Research Paper
Published 01 Jun 2021

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

  • Roslyn M. Ray,
  • Anders Højgaard Hansen,
  • Maria Taskova,
  • Bernhard Jandl,
  • Jonas Hansen,
  • Citra Soemardy,
  • Kevin V. Morris and
  • Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

Graphical Abstract
  • peptides were included in this study and modified with an N-terminal lipid anchor for LNP postinsertion. The design of the lipid anchor includes two palmitoyl chains that are attached through a 1,2-diaminopropanoic acid moiety (Dap) on the N-terminus of each peptide, providing the lipidated peptides
PDF
Album
Supp Info
Full Research Paper
Published 26 Apr 2021

Synthetic strategies of phosphonodepsipeptides

  • Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

Graphical Abstract
  • chlorination. After the treatment of compound 39 with piperidine, the N-terminal free dipeptide was obtained and acylated with hexanedioic anhydride to afford the designed hapten 40 (Scheme 7) [11]. Phosphonodepsioctapeptide 41 was prepared as a variation of the partial sequence of a gene product of erb B-2
PDF
Album
Review
Published 16 Feb 2021

Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement

  • Vladimir Kubyshkin,
  • Rebecca Davis and
  • Nediljko Budisa

Beilstein J. Org. Chem. 2021, 17, 439–460, doi:10.3762/bjoc.17.40

Graphical Abstract
  • starts immediately after the synthesis, inside the ribosome tunnel. The tunnel accommodates between 30 and 40 amino acid residues [93][94]. The trigger factor (gene tig) is a generic chaperone that facilitates the folding of the N-terminal protein section emerging from the ribosome [95]. The proline
  • stability effects when incorporated at the positions Pro-4 and Pro-7, despite the fact that both residues are located in the N-terminal PII helix. This result was interpreted by differences in the local polar interactions created by the carbon–fluorine bond within the interior of the foldon domain [106
PDF
Album
Review
Published 15 Feb 2021

19F NMR as a tool in chemical biology

  • Diana Gimenez,
  • Aoife Phelan,
  • Cormac D. Murphy and
  • Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

Graphical Abstract
  • -structural protein 1 (NS1A) homodimer (Figure 9) [64]. Protein NS1A is a highly conserved virulence factor from influenza virus (H3N2) comprised of an N-terminal double-stranded RNA (dsRNA)-binding domain (RBD) and a multifunctional C-terminal effector domain (ED), each of which can independently form
  • -like environments. Specifically, the N-terminal region of the peptide, which includes the first 4-tfmF-labelled amino acid, was shown to be involved in the most important membrane-binding interactions and conformational changes observed, allowing the protein to adopt a metastable aggregation-prone
PDF
Album
Review
Published 28 Jan 2021

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

Graphical Abstract
  • of the N-terminal of the branch increased the stability of the branched peptides. Moreover, these branched peptides facilitate the delivery of the proteins into cells. This work contributes insights for the development of peptide supramolecular assemblies via enzymatic noncovalent synthesis in
  • cellular environment. Keywords: acetylation; branched peptides; enzyme; nanostructures; N-terminal; responsive; self-assembly; Introduction Peptides, being able to self-assemble to exhibit emergent properties and functions [1][2][3][4][5], have received considerable attentions recently. For example
  • proteolysis to cleave the branch off 1, the micelles turn into nanofibers. Acetylation of the N-terminal of the branch forms 2, which exhibits an enhanced stability towards the proteolysis. In addition, the cleavage also occurs at other sites in the branch of 2, albeit less frequently, due to the acetylation
PDF
Album
Supp Info
Full Research Paper
Published 04 Nov 2020

NMR Spectroscopy of supramolecular chemistry on protein surfaces

  • Peter Bayer,
  • Anja Matena and
  • Christine Beuck

Beilstein J. Org. Chem. 2020, 16, 2505–2522, doi:10.3762/bjoc.16.203

Graphical Abstract
  • using shaped pulses that are specific for the respective side chain nitrogen atom (≈33 ppm for Lys Nζ and ≈85 ppm for Arg Nε). N-terminal glycine residues are also visible in the Lys-specific spectrum because the chemical shifts of the CαH2-NH3+ moiety also match the selected chemical shift range. Not
PDF
Album
Review
Published 09 Oct 2020

GlypNirO: An automated workflow for quantitative N- and O-linked glycoproteomic data analysis

  • Toan K. Phung,
  • Cassandra L. Pegg and
  • Benjamin L. Schulz

Beilstein J. Org. Chem. 2020, 16, 2127–2135, doi:10.3762/bjoc.16.180

Graphical Abstract
  • cysteines was set as a fixed modification, and dynamic modifications included deamidation of asparagine, monooxidised methionine, and the formation of pyroglutamate at N-terminal glutamic acid and glutamine. All variable modifications were set as “Common 1” allowing each modification to be present once on a
PDF
Album
Supp Info
Full Research Paper
Published 01 Sep 2020

Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA

  • Annike Weißenstein,
  • Myroslav O. Vysotsky,
  • Ivo Piantanida and
  • Frank Würthner

Beilstein J. Org. Chem. 2020, 16, 2032–2045, doi:10.3762/bjoc.16.170

Graphical Abstract
  • developed several series of fluorophore–amino acid conjugates, thereby making use of the availability of C- and N-terminal amino acid residues for peptide-bond formation. Also, several short multichromophoric peptide constructs were prepared and studied with regard to their interactions with DNA/RNA [11][12
PDF
Album
Supp Info
Full Research Paper
Published 19 Aug 2020

A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA

  • Ekaterina A. Bryushkova,
  • Erik R. Gandalipov and
  • Julia V. Nuzhina

Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100

Graphical Abstract
  • the N-terminal domain (NTD). In vitro studies demonstrated that the progressive expansion of the length of the CAG repeat in NTD decreased its transactivation function. Exons 2 and 3 code the central DNA-binding domain and exons 4 to 8 code the C-terminal ligand-binding domain [14][15]. There are
PDF
Album
Supp Info
Full Research Paper
Published 27 May 2020

Fluorinated phenylalanines: synthesis and pharmaceutical applications

  • Laila F. Awad and
  • Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

Graphical Abstract
  • 148 in variable yields with partial racemization. Phthalimido and trifluoroacetyl N-terminal protecting groups (R1 = Phth or TFA) and unprotected C-terminal derivatives (R2 = H) provided the most efficient outcomes (80 and 67% yield, respectively). An N-acetyl group was also suitable as protecting
  • group for the reaction providing the desired product with 57% yield. Also, methyl and ethyl esters as C-terminal protecting groups in combination with phthalimino as the N-terminal protecting group, were both successfully explored. However, when the trifluoroacetyl amide was used as a substrate the
PDF
Album
Review
Published 15 May 2020

Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides

  • Sabrina Müller,
  • Jannik Paulus,
  • Jochen Mattay,
  • Heiko Ihmels,
  • Veronica I. Dodero and
  • Norbert Sewald

Beilstein J. Org. Chem. 2020, 16, 60–70, doi:10.3762/bjoc.16.8

Graphical Abstract
  • required because this allowed for an alignment between hydrogen-bonding groups in long polyamides and in the minor groove of DNA [41]. The Fmoc-protected heterocyclic amino acids 2 were obtained from N-methylpyrrole and N-methylimidazole, respectively (Scheme 2A). The N-terminal N-methylpyrrole and N
  • -methylimidazole units were introduced by employing diamino derivatives 3 (Scheme 2A) [40]. Moreover, it turned out that coupling the subsequent building block to an N-terminal Im building block was problematic because the amino group of the imidazole derivative 2b is a weak nucleophile, and therefore the Fmoc–Py
PDF
Album
Supp Info
Full Research Paper
Published 09 Jan 2020

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

Graphical Abstract
  • , acid-mediated deprotection of the Boc group and final coupling to Boc-ᴅ-alanine. Fully protected tripeptides were transformed by base hydrolysis into the free carboxylic acids, followed by activation of the unprotected C-terminus as a SNAc thioester. Subsequent cleavage of the N-terminal Boc protecting
PDF
Album
Supp Info
Full Research Paper
Published 05 Dec 2019
Other Beilstein-Institut Open Science Activities