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Search for "amino acid" in Full Text gives 550 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

New variochelins from soil-isolated Variovorax sp. H002

  • Jabal Rahmat Haedar,
  • Aya Yoshimura and
  • Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

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  • serine (Ser), a β-hydroxyaspartic acid (Hya), and a unique γ-amino acid biosynthetically originating from an arginine and a methyl malonate (4-amino-7-guanidino-3-hydroxy-2-methylheptanoic acid), with the amino group acylated by a saturated fatty acid. Subsequent HMBC and MS/MS analyses indicated that
  • C45H79O17N11, as suggested by the HRESIMS data (m/z 1044.5603 for the [M − H]− ion), indicating the loss of two methylene groups (C2H4) from 1. In addition, the MS/MS fragmentation profile of 3 was consistent with those of 1 and 2, except for the loss of 28 mass units in the N-terminal Nγ-acyl-γ-amino acid
  • ][18]. The absolute configurations of the amino acid constituents, Pro, Ser and two modified ornithine residues, in 3–5 were assigned as ʟ, ᴅ, and ʟ, respectively (Figures S25, S33, and S41, Supporting Information File 1). The geometry of the olefins in 4 and 5 was determined to be Z based on the 13C
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Published 02 Apr 2024

Palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines

  • Geng-Xin Liu,
  • Xiao-Ting Jie,
  • Ge-Jun Niu,
  • Li-Sheng Yang,
  • Xing-Lin Li,
  • Jian Luo and
  • Wen-Hao Hu

Beilstein J. Org. Chem. 2024, 20, 661–671, doi:10.3762/bjoc.20.59

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  • -light-mediated palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines, affording unsaturated γ- and ε-amino acid derivatives with diverse structures. In this methodology, the diazo compound readily transforms into a hybrid α-ester
  • -amino acid derivative. This approach proceeds under mild and simple reaction conditions and shows high functional group tolerance, especially in the incorporation of various bioactive molecules. The studies on scale-up reactions and diverse derivatizations highlight the practical utility of this
  • temperature (rt), the desired unsaturated ε-AA derivative 4a was obtained in 75% isolated yield (Table 1, entry 1). Isolation and NMR analysis demonstrated that this model reaction provided amino acid 4a with good E-selectivity and excellent regioselectivity (E/Z = 91:9, 1,4-/1,2-addition >20:1). Control
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Published 27 Mar 2024

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

  • Michael O. Akintubosun and
  • Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

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  • . Interestingly, this cluster is separated into two groups. All the sequences that group with Hyg17 are found in identical hygromycin A biosynthetic clusters. The second group has 12 of the 29 Hyg genes with greater than 30% amino acid identity (Figure 4b and Supporting Information File 1, Table S2). The strains
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Published 14 Mar 2024

Recent developments in the engineered biosynthesis of fungal meroterpenoids

  • Zhiyang Quan and
  • Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 578–588, doi:10.3762/bjoc.20.50

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  • sequential reaction to produce the spirolactone 27. In contrast, PrhA dehydrogenates H-1 of 26 to form the heptadiene 28. Comparing the active centers, only three amino acid residues differ between AusE and PrhA: L150(AusE)/V150(PrhA), S232(AusE)/A232(PrhA), and V241(AusE)/M241(PrhA). By swapping these
  • preandiloid C (58), and generates a radical leading to the construction of the bicyclo[2.2.2]octane skeleton of andiconin (59) (Figure 8) [36][37]. Two amino acid pairs, M119/N121 and A228/A230, in its substrate-binding pocket were mutated by saturation mutagenesis using degenerate primers, resulting in an
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Published 13 Mar 2024

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

  • Rattiya Janthanom,
  • Yuta Kikuchi,
  • Hiroki Kanto,
  • Tomoyasu Hirose,
  • Arisu Tahara,
  • Takahiro Ishii,
  • Arinthip Thamchaipenet and
  • Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

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  • HCl. The obtained amino acid (alanine) and authentic amino acids were modified using Nα-(5-fluoro-2,4-dinitrophenyl)-ᴅ-leucinamide (ᴅ-FDLA). The LC–MS analysis of ᴅ-FDLA derivatives revealed that the chiral center of the amino acid in 1 had ʟ configuration (Figure S7, Supporting Information File 1
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Published 29 Feb 2024

Development of a chemical scaffold for inhibiting nonribosomal peptide synthetases in live bacterial cells

  • Fumihiro Ishikawa,
  • Sho Konno,
  • Hideaki Kakeya and
  • Genzoh Tanabe

Beilstein J. Org. Chem. 2024, 20, 445–451, doi:10.3762/bjoc.20.39

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  • arm in an adjacent peptidyl carrier protein (PCP). The amino acid loaded on the PCP then undergoes coupling with the amino acid loaded on the downstream PCP in the condensation (C) domain. Finally, the linear peptide on the PCP in the last module is either hydrolyzed or cyclized by a thioesterase (TE
  • activities against the A-domain of MbtA, a component of mycobactin synthetase and antimicrobial activities against M. tuberculosis [7]. In addition, aminoacyl (AA)-AMS has been designed to inhibit the amino acid-activating A-domains in NRPSs and has been found to be a tight-binding inhibitor (Figure 2b) [8
  • probes (AA-AMS-BPyne) can selectively label the A-domains corresponding to the amino acid of the ligand in both recombinant enzymes and proteomes. We recently reported that these probes can be used to label the A-domains of endogenous NRPSs in live bacterial cells [17][18][19]. The intracellular labeling
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Published 26 Feb 2024

Discovery of unguisin J, a new cyclic peptide from Aspergillus heteromorphus CBS 117.55, and phylogeny-based bioinformatic analysis of UngA NRPS domains

  • Sharmila Neupane,
  • Marcelo Rodrigues de Amorim and
  • Elizabeth Skellam

Beilstein J. Org. Chem. 2024, 20, 321–330, doi:10.3762/bjoc.20.32

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  • 2 was determined by Marfey’s method. A biosynthetic gene cluster (BGC) encoding unguisins B and J was compared to characterized BGCs in other Aspergillus sp. Since the unguisin family of heptapetides incorporate different amino acid residues at different positions of the peptide, the A and C domains
  • heptapeptides isolated predominantly from Aspergillus sp. [1][2][3][4][5][6][7][8]. Distinctive features of these cyclic peptides include the non-proteinogenic amino acid γ-aminobutyric acid (GABA) and the incorporation of up to five ᴅ-amino acids (Figure 1) [1][2][3][4][5][6][7][8]. The amino acids at
  • , 7.33, 7.07 and 6.97 ppm, exhibiting key 1H,1H-COSY and HMBC correlations, suggested a tryptophan aromatic amino acid portion (Figure 3). The other six amino acid residues were assigned based on 2D NMR spectra (1H-1H COSY, HSQC and HMBC) as Ala (2 equiv), Phe (1 equiv), Leu (1 equiv), Val (1 equiv), and
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Published 19 Feb 2024

Catalytic multi-step domino and one-pot reactions

  • Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

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  • . Zhang, Ma, and W. Zhang reflects the state of the art in the α-amino acid-based [3 + 2] cycloaddition reactions of N–H-type azomethine ylides in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse bioactive heterocyclic compounds and natural products [9]. Computational studies
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Editorial
Published 08 Feb 2024

Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

  • Milandip Karak,
  • Cian R. Cloonan,
  • Brad R. Baker,
  • Rachel V. K. Cochrane and
  • Stephen A. Cochrane

Beilstein J. Org. Chem. 2024, 20, 220–227, doi:10.3762/bjoc.20.22

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  • mixture which were then purified to give the desired α-anomers. Thioglycosides 1c, 1d, and 1f were isolated purely as β-anomers due to anchimeric assistance from the C2 N-acetyl or N-Troc groups. In glycosyl acceptors, the first amino acid of the lipid II pentapeptide, Ala, was incorporated as a 2
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Published 06 Feb 2024

Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

  • Youlong Du,
  • Haibo Mei,
  • Ata Makarem,
  • Ramin Javahershenas,
  • Vadim A. Soloshonok and
  • Jianlin Han

Beilstein J. Org. Chem. 2024, 20, 212–219, doi:10.3762/bjoc.20.21

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  • over 50% of agricultural chemicals contain at least one fluorine atom, among which architectural motifs containing fluorine and amino acid residues are a fast-growing segment of modern pharmaceuticals [10][11][12][13]. Fluoroalkyldiazo compounds belong to the most versatile and valuable reagents in
  • example, Wan and co-workers developed a cascade reaction of α-diazo esters, nitriles, and carboxylic acids via the generation of nitrile ylides and Mumm rearrangement affording unsymmetric diacyl α-amino acid esters as products (Scheme 1a) [39]. In 2017, Zhang, Hu, and co-workers developed a Cu-catalyzed
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Published 02 Feb 2024

Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway

  • Seiji Kawai,
  • Akito Yamada,
  • Yohei Katsuyama and
  • Yasuo Ohnishi

Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1

Graphical Abstract
  • ) [13]. CmaA2 and CmaA3 showed relatively high amino acid sequence similarity to AvaA2 and AvaA3, respectively (≈50% identity; see Table S2 in Supporting Information File 1). In contrast, low similarities were observed between CmaA2 and AvaA3, and between CmaA3 and AvaA2 (Table S2, Supporting
  • CmaA2 and CmaA3 for CmaA1) is a matter of interest. The fact that AvaA1 and CmaA1 recognized CmaA3 and AvaA3, respectively, as partner ACP suggests that there are some important residues conserved between AvaA3 and CmaA3 for the ligase–ACP interaction. Indeed, two amino acid residues (Trp38 and His41 of
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Published 02 Jan 2024

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

  • Xiaofeng Zhang,
  • Xiaoming Ma and
  • Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

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  • with arylaldehydes are much less explored. The [3 + 2] adducts of α-amino acids could be used for a second [3 + 2] cycloaddition as well as for other post-condensation modifications. This article highlights our recent work on the development of α-amino acid-based [3 + 2] cycloaddition reactions of N–H
  • stereoselectivity which limits the synthetic utility of non-stabilized AMYs of type C. There are over 300 papers on the amino acid-based decarboxylative [3 + 2] cycloadditions of N–R-type AMYs B1 (such as that derived from proline) and B2 [31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49
  • aldehydes and alkenes. The first cycloaddition products 3c or 3d can also be used as intermediates for other transformations to synthesize novel heterocyclic rings via multicomponent, one-pot, and stepwise synthesis [63][64]. Presented in the following sections is our work on the development of amino acid
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Perspective
Published 06 Nov 2023

Tying a knot between crown ethers and porphyrins

  • Maksym Matviyishyn and
  • Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

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  • complexes, the fragment originating from the porphyrinoid could form hydrogen bonds with a carboxyl group, while the crown ether cavity would allow interaction with the protonated amine group of an amino acid molecule. The choice of macrocycle size could enable the recognition of different biomolecules
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Published 27 Oct 2023

Radical chemistry in polymer science: an overview and recent advances

  • Zixiao Wang,
  • Feichen Cui,
  • Yang Sui and
  • Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

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  • amino acid sequence of mfp-1, mfp-3, and mfp-5 (Y: DOPA, K: lysine). B) Scheme showing examples of the adhesive and cohesive properties of catechol-containing proteins. R represents the remainder of the mfp’s. Scheme 3 redrawn from [10]. Activation–deactivation equilibrium in nitroxide-mediated
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Published 18 Oct 2023

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

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  • diphosphate synthase (FPPS) and 2MIBS from Streptomyces coelicolor [26] (Scheme 1B). Crystal structures of both enzymes have been obtained [27][28] and allowed for a deep structure-based investigation of 2MIBS through site-directed mutagenesis [29]. The predicted amino acid sequences of 2MIBS homologs from
  • alignment with the short 2MIBS from Longispora albida DSM 44784 (WP_018349754) the border between domains A and B in the 2MIBS from S. coelicolor was identified. Domain A spans the amino acid residues 1–115 and domain B includes the amino acid residues 115–440. The gene sequences for both domains were
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Published 22 Sep 2023

α-(Aminomethyl)acrylates as acceptors in radical–polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping

  • Angel Palillero-Cisneros,
  • Paola G. Gordillo-Guerra,
  • Fernando García-Alvarez,
  • Olivier Jackowski,
  • Franck Ferreira,
  • Fabrice Chemla,
  • Joel L. Terán and
  • Alejandro Perez-Luna

Beilstein J. Org. Chem. 2023, 19, 1443–1451, doi:10.3762/bjoc.19.103

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  • . Trapping of this enolate would lead to β-amino acid units, a class of compounds that has attracted a great deal of attention [19][20][21][22][23][24]. An obvious possible shortcoming that had to be considered was still that the generated zinc enolate III having a β-amino group could undergo β-elimination
  • . Importantly, the protocol was found to be similarly applicable with enoates 8b (Table 3, entry 6) and 8c (entry 7) having tert-butyl and benzyl ester groups, which, as the methyl ester unit, are typical in the context of amino acid synthesis. ZnBu2 was also amenable to 1,4-addition (Table 3, entry 8), but not
  •  5). Product (RS)-14b (85:15 dr), i.e., a mixture of two enantiomerically pure diastereomers, was obtained from (RS)-tert-butylsulfinamide upon allylation with tert-butyl α-(bromomethyl)acrylate followed by 1,4-addition with Et2Zn. It was then converted into the known β2-amino acid 17 by TFA-promoted
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Published 21 Sep 2023

Functional characterisation of twelve terpene synthases from actinobacteria

  • Anuj K. Chhalodia,
  • Houchao Xu,
  • Georges B. Tabekoueng,
  • Binbin Gu,
  • Kizerbo A. Taizoumbe,
  • Lukas Lauterbach and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1386–1398, doi:10.3762/bjoc.19.100

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  • synthase homologs from diverse actinobacteria that were selected based on a phylogenetic analysis of more than 4000 amino acid sequences were investigated for their products. For four enzymes with functions not previously reported from bacterial terpene synthases the products were isolated and their
  • , Supporting Information File 1). The closest characterised terpene synthase with an amino acid sequence identity of 25% is the (1(10)E,4E,6S,7R)-germacradien-6-ol synthase from Streptomyces pratensis [33]. The recombinant enzyme efficiently converted FPP into one sesquiterpene alcohol whose electron
  • . brevicatena (Table 1, entry 5) showed the highly conserved motifs with a modified aspartate-rich region (86DDHRN) and the NSE triad 227NDLHSMPKE (Figure S33, Supporting Information File 1). This enzyme is closely related to the epi-isozizaene synthase from S. coelicolor (EIZS) [24], but is with an amino acid
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Published 15 Sep 2023

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

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Published 28 Jul 2023
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  • as H-bond donor to the catalyst (see transition state 97, Scheme 22a) [51]. Recently, the same research group documented another aza-Friedel–Crafts reaction between indoles 4 and 95 that frames aza-quaternary stereocenter at the α-carbon of unnatural amino acid derivatives 96. Enantiocontrol was
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Published 28 Jun 2023

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

  • Dileep Kumar Singh and
  • Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

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  • ). This reaction has been successfully used for common amines using acetic acid and water, but benzylamines and benzamides show no reaction under aqueous conditions. In the case of amino acid ester hydrochlorides, the reaction to give pyrrole can be carried out without the need for the two-phase
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Published 27 Jun 2023

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine

  • Alessio Regni,
  • Francesca Bartoccini and
  • Giovanni Piersanti

Beilstein J. Org. Chem. 2023, 19, 918–927, doi:10.3762/bjoc.19.70

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  • selectively targeted by photoredox catalysis to enable unprecedented modification of the amino acid. In this context, it is worth mentioning that the single-electron oxidation of the indole moiety in tryptophan provides the radical cation, which enables selective C-radical generation at the weaker benzylic
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Published 26 Jun 2023

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes

  • Alena V. Dmitrieva,
  • Oleg A. Levitskiy,
  • Yuri K. Grishin and
  • Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41

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  • electrochemically induced oxidative modification of the amino acid side chain. Experimental and DFT studies showed that the additional tert-butyl group increases the dispersion interactions in the Ni coordination environment making the complexes more conformationally rigid and provides a higher level of
  • complex. Solubility of the t-Bu-containing ligand and its Schiff base complexes is increased, facilitating scaling-up the reaction procedure and isolation of the functionalized amino acid. Keywords: asymmetric synthesis; chiral auxiliaries; cysteine derivatives; Ni–Schiff base complexes; voltammetry
  • )) and includes a chiral auxiliary, an amino acid, and a bifunctional linker capable to arrange the components in the Schiff base complex. Such templates provide a significant C–H acidity at the α-amino acid carbon and a possibility for recycling of the chiral auxiliaries (for reviews see [5][14][15][16
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Published 27 Apr 2023

Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

  • Josipa Matić,
  • Tana Tandarić,
  • Marijana Radić Stojković,
  • Filip Šupljika,
  • Zrinka Karačić,
  • Ana Tomašić Paić,
  • Lucija Horvat,
  • Robert Vianello and
  • Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

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  • Biotechnology, Division of Molecular Biology, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia 10.3762/bjoc.19.40 Abstract Two novel conjugate molecules were designed: pyrene and phenanthridine-amino acid units with a different linker length between the aromatic fragments. Molecular
  • formed an exciplex [15], and conjugates formed of pyrene and an amino acid-fluorescent nucleobase derivative qAN1, differing in length and flexibility between fluorophores [16]. Due to pre-organization, both conjugates strongly interacted with ds-DNA/RNA grooves with similar affinity but opposite
  • ), differing only in the linker length between the aromatic units, have been prepared by condensation of two different pyrenecarboxylic acids with phenanthridine-labelled amino acid (Scheme 2). The influence of the linker length on the molecule flexibility, intramolecular conformation, spectroscopic properties
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Published 26 Apr 2023

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

  • Austin Pounder,
  • Eric Neufeld,
  • Peter Myler and
  • William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

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  • desired carboaminated product in slightly diminished yields while azabicyclic alkenes generated the targeted products in excellent yield, albeit with slightly reduced enantioselectivity. To showcase the synthetic capabilities of this methodology, the authors synthesized the non-natural amino acid
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Published 24 Apr 2023

Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

  • Louis Monsigny,
  • Floriane Doche and
  • Tatiana Besset

Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35

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  • described the selective palladium-catalyzed ortho-2,2,2-trifluoroethoxylation of a series of benzaldehydes (Scheme 22, 35 examples) using the amino acid ʟ-valine in the presence of K2S2O8 and TFA at 80 °C [153]. This reaction proved to be highly tolerant to various substituents including a CF3 group at the
  • plausible mechanism. The amino acid acts as an organocatalyst and first reacts with the benzaldehyde 47 to generate the transient directing group (47’). Then, formation of the palladacycle (species R) followed by its oxidation to a Pd(IV) intermediate and a ligand exchange with 2,2,2-trifluoroethanol leads
  • and Wang used a similar approach for the 2,2,2-trifluoroethoxylation of benzaldehydes under palladium catalysis using the amino acid 51 as organic catalyst in the presence of the fluoropyridinium salt 52 (19 examples, up to 88% yield, Scheme 23) [183]. Pleasingly, the methodology was extended to the
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Published 17 Apr 2023
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