2-Heteroarylethylamines in medicinal chemistry: a review of 2-phenethylamine satellite chemical space

• Carlos Nieto,
• Alejandro Manchado,
• Ángel García-González,
• David Díez and
• Narciso M. Garrido

Beilstein J. Org. Chem. 2024, 20, 1880–1893, doi:10.3762/bjoc.20.163

• activity. 2-Aminoethylthiophene derivatives with therapeutic activity, part 1. 2-Aminoethylthiophene derivatives with therapeutic activity, part 2. 2-Aminoethylthiophene derivatives with therapeutic activity, part 3. 2-Aminoethylpyrrole derivatives with therapeutic activity. Histamine metabolic pathway. 2

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• reports on the biosynthetic pathways from tryptophan to quinoline rings. Through our analysis, we discovered that tryptophan in the primary metabolic pathway is primarily catalyzed by indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase (IDO and TDO), as well as canine urinary tryptophan 3

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

• metabolic enzymes converting glutamate [111]. The bacteria are grown in a modified M9 minimal medium containing the labeled amino acid, all others in unlabeled form, and the corresponding metabolic pathway inhibitors. To our knowledge, this method has not been applied to study the binding of ligands that

Recent advances in Cu-catalyzed C(sp³)–Si and C(sp³)–B bond formation

• Balaram S. Takale,
• Ruchita R. Thakore,
• Elham Etemadi-Davan and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

• functional groups into existing or new drugs. Examples include the incorporation of silicon bioisosteres that help increase lipophilicity, subsequently altering the existing metabolic pathway of a drug due to differences in its physicochemical properties [8]. On the other hand, the trigonal planar nature of

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

• Eric J. N. Helfrich,
• Geng-Min Lin,
• Christopher A. Voigt and
• Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

• lines is achieved through the recombination of module series (trans-AT PKSs) [34], the exchange of large subdomains (NRPSs) [35], and the duplication followed by diversification of entire modules (NRPSs and cis-AT PKSs) [36]. As a result, dysfunctionality is a constant threat for a metabolic pathway

Analysis of sesquiterpene hydrocarbons in grape berry exocarp (Vitis vinifera L.) using in vivo-labeling and comprehensive two-dimensional gas chromatography–mass spectrometry (GC×GC–MS)

• Philipp P. Könen and
• Matthias Wüst

Beilstein J. Org. Chem. 2019, 15, 1945–1961, doi:10.3762/bjoc.15.190

• mevalonate-dependent biosynthesis pathway (MVA) localized in the cytoplasm as well as via the mevalonate-independent 1-deoxy-ᴅ-xylulose 5-phosphate/2-C-methyl-ᴅ-erythritol 4-phosphate metabolic pathway (DOXP/MEP) localized in plastids [5]. In the MVA pathway, which was first described in yeast and animals

• after administration of the precursor [6,6,6-2H3]-(±)-mevalonolactone (d3-MVL) can be found in Supporting Information File 4. Steele et al. described the formation of α-humulene via a trans-humulyl cation [9]. This metabolic pathway could also be confirmed by feeding experiments. Conclusion In summary

The enzymes of microbial nicotine metabolism

• Paul F. Fitzpatrick

Beilstein J. Org. Chem. 2018, 14, 2295–2307, doi:10.3762/bjoc.14.204

• steps in the pyrrolidine pathway. This review summarizes the present status of our understanding of these pathways, focusing on what is known about the individual enzymes involved. Keywords: biodegradation; enzyme mechanism; flavoprotein; metabolic pathway; nicotine; Introduction The toxic alkaloid (S

• -trihydroxypyridine are unclear. The compound can oxidatively dimerize to form nicotine blue [44], which is secreted into the medium. However, this has been proposed to be a byproduct, with the major pathway involving formation of maleamate, maleate, and fumarate [45]. The pyrrolidine pathway The metabolic pathway

From chemical metabolism to life: the origin of the genetic coding process

• Antoine Danchin

Beilstein J. Org. Chem. 2017, 13, 1119–1135, doi:10.3762/bjoc.13.111

Opportunities and challenges for the sustainable production of structurally complex diterpenoids in recombinant microbial systems

• Katarina Kemper,
• Max Hirte,
• Markus Reinbold,
• Monika Fuchs and
• Thomas Brück

Beilstein J. Org. Chem. 2017, 13, 845–854, doi:10.3762/bjoc.13.85

• , fragrances, fuels and fuel additives. Central building blocks of all terpenes are the isoprenoid compounds isopentenyl diphosphate and dimethylallyl diphosphate. Bacteria like Escherichia coli harbor a native metabolic pathway for these isoprenoids that is quite amenable for genetic engineering. Together

• terpene producing Escherichia coli, this review shall give an insight in recent progresses regarding manipulation of mostly diterpene synthases. Keywords: enzyme engineering; heterologous production in E. coli; metabolic pathway optimization; modular biosynthesis; plant diterpenes; Introduction

Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

• Anne-Katrin Späte,
• Verena F. Schart,
• Julia Häfner,
• Andrea Niederwieser,
• Thomas U. Mayer and
• Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

• -azidoacetylmannosamine (ManNAz) and subsequently to the corresponding sialic acid [32][33] following a metabolic pathway known also for the natural sugars [34]. Also, the efficiency by which non-natural GlcNAc and GalNAc derivatives are metabolized is dependent on the type of modification and the cell line. These

Biosynthesis of rare hexoses using microorganisms and related enzymes

• Zijie Li,
• Yahui Gao,
• Hideki Nakanishi,
• Xiaodong Gao and
• Li Cai

Beilstein J. Org. Chem. 2013, 9, 2434–2445, doi:10.3762/bjoc.9.281

• ). Alternatively, it was reported that L-galactose could be biosynthesized by epimerizing D-glucose through a novel but rare metabolic pathway during the biosynthesis of a sulfated L-galactan in the ascidian tunic, requiring a triple epimerization which brings about inversion of the configuration of carbon 2, 3

Coupled chemo(enzymatic) reactions in continuous flow

• Ruslan Yuryev,
• Simon Strompen and
• Andreas Liese

Beilstein J. Org. Chem. 2011, 7, 1449–1467, doi:10.3762/bjoc.7.169

• field and which can be used for the classification of existing biotransformations. One of these principles is that a single reaction step of a given metabolic pathway proceeds in a very specific manner due to the intrinsically high chemo-, regio- and stereoselectivity of the enzyme catalyzing this step

• clustering the enzymes of a given metabolic pathway. Moreover, the clustered enzymes usually form supramolecular complexes enabling so-called “substrate channeling”, where intermediates of sequential metabolic steps are not released into the cytoplasm, but instead are “channeled” from one enzyme to another

Bioorthogonal metabolic glycoengineering of human larynx carcinoma (HEp-2) cells targeting sialic acid

• Arne Homann,
• Riaz-ul Qamar,
• Sevnur Serim,
• Petra Dersch and
• Jürgen Seibel

Beilstein J. Org. Chem. 2010, 6, No. 24, doi:10.3762/bjoc.6.24

• -acetylneuraminic acid (Neu5Ac, 1) and mammalian N-glycolylneuraminic acid (Neu5Gc, 2). N-(1-oxohex-5-ynyl)neuraminic acid (Neu5Hex, 3) is used for bioorthogonal metabolic labelling of human larynx carcinoma (HEp-2) cells. Synthesis of N-(1-oxohex-5-ynyl)neuraminic acid (Neu5Hex 3). Metabolic pathway of Ac4GlcNAz

• kinase; ATP: adenosine triphosphate; PEP: phosphoenolpyruvate; CTP: cytidine triphosphate; PPi: pyrophosphate; DNA: deoxyribonucleic acid; mRNA: messenger ribonucleic acid. Proposed metabolic pathway of Neu5Hex 3 based on known mechanisms of Neu5Gc 2 uptake [5]. TGN: trans-Golgi network, CMP: cytidine