Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex

• Maurizio Iannuzzi,
• Thomas Hohmann,
• Michael Dyrks,
• Kilian Haoues,
• Katarzyna Salamon-Krokosz and
• Beate Koksch

Beilstein J. Org. Chem. 2025, 21, 659–669, doi:10.3762/bjoc.21.52

• -trifluoromethylphenylalanine ([2.3.5.6F]TfMePhe, 2) and bis(trifluoromethyl)phenylalanine (bisTfMePhe, 3) (Scheme 1). Neither amino acid has, to our knowledge, been described in the context of peptide chemistry yet. In general, fluorinated aromatic amino acids are essential building blocks that allow a modification of

• , which have yet to be described in the context of peptide chemistry. The several CF3 groups employ a strong inductive effect on the aromatic ring structure, making these amino acids highly interesting building blocks for modification of aromatic–aromatic interactions in the context of protein folding

Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation

• Perry van der Heide,
• Michele Retini,
• Fabiola Fanini,
• Giovanni Piersanti,
• Francesco Secci,
• Daniele Mazzarella,
• Timothy Noël and
• Alberto Luridiana

Beilstein J. Org. Chem. 2024, 20, 3274–3280, doi:10.3762/bjoc.20.271

• , forming a new C(sp3)–C(sp3) bond. The reaction can be performed in a phosphate-buffered saline (PBS) solution and shows post-functionalization prospects through pathways involving classical peptide chemistry. Keywords: dehydroalanine; Giese-type reaction; hydroalkylation; photocatalysis; water

A versatile way for the synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH₄/I₂ system

• Lin Chen,
• Xuan Zhou,
• Zhiyong Chen,
• Changxu Wang,
• Shunjie Wang and
• Hanbing Teng

Beilstein J. Org. Chem. 2022, 18, 1032–1039, doi:10.3762/bjoc.18.104

• particularly suitable for peptide chemistry since protecting groups are often required in peptide synthesis [52][53]. These multistep reaction methods are conducive to avoid overmethylation products. Although procedures for the synthesis of monomethylamines have been developed over the past years, the starting

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• amino acids and peptide scaffolds compatible with the transformation. The late-stage oxidation of proline 76 to 5-hydroxyproline furnished interesting intermediates, giving access to relevant motifs in peptide chemistry (Scheme 27C). Sesquiterpenes are known to present complex polycyclic structures with

Selected peptide-based fluorescent probes for biological applications

• Debabrata Maity

Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247

• Attribution 3.0 Unported Licence, https://creativecommons.org/licenses/by/3.0/. Published by The Royal Society of Chemistry. Acknowledgements The author would like to thank late Prof. Dr. Carsten Schmuck for his exceptional contribution to Supramolecular Chemistry and Peptide Chemistry research.

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

• demonstrate the enormous influence of branching on the overall yield yoa and synthesis efficiency Effsyn. Fragment strategy: fragment linking in peptides synthesis In synthetic peptide chemistry, amino acids are sequentially built up to form long oligo/polypeptides. For reasons of transparency, we have

Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

• Razieh Navari,
• Saeed Balalaie,
• Saber Mehrparvar,
• Fatemeh Darvish,
• Frank Rominger,
• Fatima Hamdan and
• Sattar Mirzaie

Beilstein J. Org. Chem. 2019, 15, 874–880, doi:10.3762/bjoc.15.85

• Razieh Navari Saeed Balalaie Saber Mehrparvar Fatemeh Darvish Frank Rominger Fatima Hamdan Sattar Mirzaie Peptide Chemistry Research Center, K. N. Toosi University of Technology, P. O. Box 15875-4416, Tehran, Iran, Tel: +98-21-23064226, Fax: +98-21-22889403 Medical Biology Research Center

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

• Eszter Lajkó,
• Sarah Spring,
• Rózsa Hegedüs,
• Beáta Biri-Kovács,
• Sven Ingebrandt,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

• Kaiserslautern, Amerikastraße 1, 66482 Zweibrücken, Germany Research Group of Peptide Chemistry, Hungarian Academy of Sciences, Eötvös Loránd University, Pázmány Péter sétány 1/A, 1117 Budapest, Hungary Eötvös Loránd University, Faculty of Science, Institute of Chemistry, Pázmány Péter sétány 1/A, 1117 Budapest

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

• mechanistic considerations are highlighted in the text when appropriate. Keywords: C–H functionalisation; heterocycles; late-stage functionalisation; medicinal chemistry; organic dyes; organic photocatalysts; peptide chemistry; photoredox catalysis; Review 1 Introduction 1.1 Main advantages of

Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

• Livia Polgár,
• Eszter Lajkó,
• Pál Soós,
• Orsolya Láng,
• Marilena Manea,
• Béla Merkely,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

• , Nagyvárad tér 4., Budapest, 1089, Hungary University of Konstanz, Department of Chemistry and Zukunftskolleg, Universitätsstrasse 10, 78467 Konstanz, Germany Eötvös Loránd University, Faculty of Science, Institute of Chemistry, Pázmány P. stny 1/A Budapest, 1117, Hungary MTA-ELTE Research Group of Peptide

• Chemistry, Pázmány P. stny 1/A, Hungarian Academy of Science, Budapest, 1117, Hungary 10.3762/bjoc.14.136 Abstract Background: Cardiomyopathy induced by the chemotherapeutic agents doxorubicin and daunorubicin is a major limiting factor for their application in cancer therapy. Chemotactic drug targeting

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

• Research Group of Peptide Chemistry, Hungarian Academy of Sciences, Eötvös Loránd University, Pázmány P. stny. 1/A, H-1117 Budapest, Hungary 10.3762/bjoc.14.80 Abstract Cancer is the second leading cause of death affecting nearly one in two people, and the appearance of new cases is projected to rise by

Development of novel cyclic NGR peptide–daunomycin conjugates with dual targeting property

• Andrea Angelo Pierluigi Tripodi,
• Szilárd Tóth,
• Kata Nóra Enyedi,
• Gitta Schlosser,
• Gergely Szakács and
• Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 911–918, doi:10.3762/bjoc.14.78

• Andrea Angelo Pierluigi Tripodi Szilard Toth Kata Nora Enyedi Gitta Schlosser Gergely Szakacs Gabor Mezo Eötvös Loránd University, Faculty of Science, Institute of Chemistry, Pázmány P. stny. 1/A, H-1117 Budapest, Hungary MTA-ELTE Research Group of Peptide Chemistry, Hungarian Academy of Sciences

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

• Sabine Schuster Beata Biri-Kovacs Balint Szeder Viktor Farkas Laszlo Buday Zsuzsanna Szabo Gabor Halmos Gabor Mezo MTA-ELTE Research Group of Peptide Chemistry, Hungarian Academy of Sciences, Eötvös L. University, 1117 Budapest, Hungary Institute of Chemistry, Eötvös L. University, 1117 Budapest

Fluorogenic PNA probes

• Tirayut Vilaivan

Beilstein J. Org. Chem. 2018, 14, 253–281, doi:10.3762/bjoc.14.17

• of protease activities (Figure 10B) [82]. The advantages of using PNA as the switch over DNA would be the excellent biological stability and the compatibility of PNA with peptide chemistry. Obviously, the ease of the opening of the beacon could be fine-tuned to accommodate the different strengths of

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• diethyl phosphonate groups [204], other mild conditions, developed in the context of peptide chemistry, were reported. It is based on the use of trimethylsilyl trifluoromethanesulfonate (TMS-OTf) as silylating agent, trifluoroacetic acid (TFA) as acidic reagent, and dimethylsulfide (DMS) and m-cresol to

Intramolecular glycosylation

• Xiao G. Jia and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

• which can be formed more readily than a glycosidic bond. ... The glycosylation reaction then becomes an intramolecular process and hence could be expected to proceed more easily.” The authors then refer to a known phenomenon in the field of peptide chemistry “where two components to be coupled had been

From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

• Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

• – combining peptide chemistry and supramolecular chemistry I learned a great deal of things during my postdoc and it was a great experience for me. However, one thing I learned was that I did not want to start out my independent career trying to design and synthesize a functional molecule (receptor, enzyme

Assembly of synthetic Aβ miniamyloids on polyol templates

• Sebastian Nils Fischer and
• Armin Geyer

Beilstein J. Org. Chem. 2015, 11, 2646–2653, doi:10.3762/bjoc.11.284

• strands, which are expected to push the esterification towards quantitative conversion. Compound 5 combines side-chain cis-diol functionality for boronic ester formation and the potential of controlled oligomerization by peptide chemistry. Azido ester 5 is a precursor of the dipeptide Hot=Tap, which

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

• Tor E. Kristensen

Beilstein J. Org. Chem. 2015, 11, 446–468, doi:10.3762/bjoc.11.51

• recognized procedure for large-scale preparation of many useful side-chain derivatives of hydroxyamino acids and related compounds. Such derivatives are useful in peptide chemistry and drug development, as amino acid amphiphiles for asymmetric catalysis, and as amino acid acrylic precursors for preparation

• chemistry, as a set of specialized techniques, useful for certain applications in peptide chemistry or in the synthesis of medicinal compounds from tyrosine or L-DOPA, besides, of course, the preparation and study of such O-acylated amino acids in itself. The employment of acidic O-acylations of

Synthetic strategies for the fluorescent labeling of epichlorohydrin-branched cyclodextrin polymers

• Milo Malanga,
• Mihály Bálint,
• István Puskás,
• Kata Tuza,
• Tamás Sohajda,
• László Jicsinszky,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3007–3018, doi:10.3762/bjoc.10.319

• -Cl. Nitrobenzofurazan is a green dye that is well-known in the field of peptide chemistry since it was first applied as a fluorogenic reagent for amino acids [28]. The high reactivity of the 4-chloro-7-nitrobenzofurazan towards amines and its peculiar spectroscopic properties make this molecule a

Synthesis of nanodiamond derivatives carrying amino functions and quantification by a modified Kaiser test

• Gerald Jarre,
• Steffen Heyer,
• Elisabeth Memmel,
• Thomas Meinhardt and
• Anke Krueger

Beilstein J. Org. Chem. 2014, 10, 2729–2737, doi:10.3762/bjoc.10.288

• bound amino groups are most versatile for the grafting of larger moieties onto the surface of nanoparticles. Typically, they are used for the formation of amides using protocols from peptide chemistry or in reductive aminations [1][2]. Additionally, amino groups have an influence on the surface polarity

Molecular architecture with carbohydrate functionalized β-peptides adopting 3₁₄-helical conformation

• Nitin J. Pawar,
• Navdeep S. Sidhu,
• George M. Sheldrick,
• Dilip D. Dhavale and
• Ulf Diederichsen

Beilstein J. Org. Chem. 2014, 10, 948–955, doi:10.3762/bjoc.10.93

• for carbohydrate and peptide chemistry. Therefore, sugar units are introduced by side-chain ligation and labeling strategies on the peptide scaffold or were established by incorporation of sugar-β-amino acids by solid-phase peptide synthesis (SPPS) [36][37]. Sugar amino acid building blocks have

Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker

• Mayeul Collot,
• Steffen Eller,
• Markus Weishaupt and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 97–105, doi:10.3762/bjoc.9.13

• issues. Cleavage of the linker by hydrogenolysis results in a free amine functionality for the immobilization of oligosaccharides on glycan arrays or for the synthesis of glycoconjugates. Hydrogenolysis on a solid support has been used previously in peptide chemistry [37]. In the early 1980s, catalytic

A novel high-yield synthesis of aminoacyl p-nitroanilines and aminoacyl 7-amino-4-methylcoumarins: Important synthons for the synthesis of chromogenic/fluorogenic protease substrates

• Xinghua Wu,
• Yu Chen,
• Herve Aloysius and
• Longqin Hu

Beilstein J. Org. Chem. 2011, 7, 1030–1035, doi:10.3762/bjoc.7.117

• was highly chemoselective, mild, and free of racemization in the coupling step [20]; was compatible with common protecting groups used in peptide chemistry including Fmoc, Boc, Cbz, and Trt; and more importantly, worked very efficiently for electron-deficient aromatic azides substituted with an

• solvents. Most importantly, the protecting groups commonly used in amino acid and peptide chemistry, such as Fmoc, Boc, Cbz, and Trt, are all well-tolerated under the present conditions. This selenocarboxylate/azide amidation strategy represents a convenient and high-yield synthesis of Nα-protected

• amino acids or their corresponding commercially available N-hydroxysuccinimide esters. The method involved the in situ formation of selenocarboxylate intermediate of protected amino acids and the subsequent non-nucleophilic amidation with an azide. Common protecting groups used in amino acid/peptide

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

• José L. Jiménez Blanco,
• Fernando Ortega-Caballero,
• Carmen Ortiz Mellet and
• José M. García Fernández

Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20

• , carbamate and thiourea-linked sugars The replacement of amide groups by pseudoamide (NH–C = X)–Y; X, Y = O, N, S) has been widely used in peptide chemistry to induce well-defined secondary structures. In carbohydrate chemistry, the incorporation of pseudoamide-type intersaccharide linkages has an additional