Computational toolbox for the analysis of protein–glycan interactions

• Ferran Nieto-Fabregat,
• Maria Pia Lenza,
• Angela Marseglia,
• Cristina Di Carluccio,
• Antonio Molinaro,
• Alba Silipo and
• Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

• proteins versatility places them at the core of almost every biological event, including cell–cell communication and regulation of immune responses. In the majority of cases, these mechanisms are significantly influenced by the molecular interactions occurring between glycans and receptor proteins. A well

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

• States 10.3762/bjoc.14.151 Abstract Quorum sensing (QS) is a cell–cell communication mechanism that enables bacteria to assess their population density and alter their behavior upon reaching high cell number. Many bacterial pathogens utilize QS to initiate an attack on their host, thus QS has attracted

Acyl-group specificity of AHL synthases involved in quorum-sensing in Roseobacter group bacteria

• Lisa Ziesche,
• Jan Rinkel,
• Jeroen S. Dickschat and
• Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 1309–1316, doi:10.3762/bjoc.14.112

• on surfaces [3]. They can produce a variety of secondary metabolites, including antibiotics [4][5], volatile compounds [6][7], oligohydroxybutyrates [8] and a range of N-acylhomoserine lactones (AHLs) [8][9][10]. AHLs are quorum-sensing signaling compounds that are used for cell–cell communication to

Versatile synthesis of the signaling peptide glorin

• Robert Barnett,
• Daniel Raszkowski,
• Thomas Winckler and
• Pierre Stallforth

Beilstein J. Org. Chem. 2017, 13, 247–250, doi:10.3762/bjoc.13.27

• evolutionary transition [1]. This transition has occurred not only once, in fact more than 25 independent instances of this event are known. The resulting increase in biological complexity requires fine-tuned differentiation and cell–cell communication mechanisms. The social amoebae are exquisite organisms to

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• ], and recently it was reported that so called photopyrones (8–15) act as signaling molecules in the cell–cell communication system of the bacterium Photorhabdus luminescens (Figure 1) [14]. Since the biological activities of α-pyrones are very diverse, these compounds are in the focus of synthetic

• function for α-pyrones within bacteria was discovered. The so called photopyrones (8–15, Figure 1) represent extracellular signals involved in cell–cell communication [14]. Photorhabdus luminescens, an entomopathogenic bacterium species, excretes these molecules, and binding of the latter to the respective

Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives

• Maroš Bella,
• Miroslav Koóš and
• Chun-Hung Lin

Beilstein J. Org. Chem. 2015, 11, 1547–1552, doi:10.3762/bjoc.11.170

• processes, such as cell–cell communication, signal transduction, activation and response of the immune system etc. [1][2]. On the other hand, an uncontrolled glycosylation caused by genetic mutations of GTs leads to structural changes in various glycoconjugates which contribute to many mammalian diseases [3

A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis

• Darko Kresovic,
• Florence Schempp,
• Zakaria Cheikh-Ali and
• Helge B. Bode

Beilstein J. Org. Chem. 2015, 11, 1412–1417, doi:10.3762/bjoc.11.152

• including a novel derivative. Moreover this novel class of ketosynthases is only distantly related to other pyrone-forming enzymes identified in the biosynthesis of the potent antibiotics myxopyronin and corallopyronin. Keywords: cell–cell communication; ketosynthase; photopyrones; pseudopyronines; quorum

• [5] and selective COX-2 inhibitors [6]. Recently, it was shown that photopyrones (Figure 1) are signaling molecules in a new cell–cell communication system in the entomopathogenic bacterium Photorhabdus luminescens. The system consists of endogenously produced photopyrones as signaling molecules and

• possible that pseudopyronines might also serve as a communication signal in strain GM30 and other Pseudomonas strains, which are generally rich in cell–cell communication signals [31][32][33][34][35]. In summary we have shown that two unusual ketosynthases are responsible for the formation of photopyrones

Synthesis of carbohydrate-scaffolded thymine glycoconjugates to organize multivalency

• Anna K. Ciuk and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2015, 11, 668–674, doi:10.3762/bjoc.11.75

• on the cell surface that are essential for cell–cell communication [1][2][3][4]. During the last two decades it has become clear that there is not one mechanism underlying multivalency effects in glycobiology, but that there are a multitude of biological processes involving multivalency in one or the

Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives

• Paola Bonaccorsi,
• Maria Luisa Di Gioia,
• Antonella Leggio,
• Lucio Minuti,
• Teresa Papalia,
• Carlo Siciliano,
• Andrea Temperini and
• Anna Barattucci

Beilstein J. Org. Chem. 2013, 9, 2410–2416, doi:10.3762/bjoc.9.278

• chemistry. Moreover, they have been investigated for their potential applications in molecular recognition, showing powerful complexation abilities toward different kinds of organic guests [3][4]. Many biological processes, such as cell–cell communication, immune response and cancer metastasis, are

An easily accessible sulfated saccharide mimetic inhibits in vitro human tumor cell adhesion and angiogenesis of vascular endothelial cells

• Grazia Marano,
• Claas Gronewold,
• Martin Frank,
• Anette Merling,
• Christian Kliem,
• Sandra Sauer,
• Manfred Wiessler,
• Eva Frei and
• Reinhard Schwartz-Albiez

Beilstein J. Org. Chem. 2012, 8, 787–803, doi:10.3762/bjoc.8.89

• as well as by interfering with the oligosaccharides of the respective integrin. Further studies are needed to show whether GSF indeed interacts with oligosaccharide binding sites on cells and therefore contributes to the inhibition of cell–cell communication. As expected from the results of the

Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations

• Baptiste Thomas,
• Michele Fiore,
• Isabelle Bossu,
• Pascal Dumy and
• Olivier Renaudet

Beilstein J. Org. Chem. 2012, 8, 421–427, doi:10.3762/bjoc.8.47

• : chemoselective ligation; click chemistry; cyclopeptide; heteroglycocluster; oxime; Introduction Multivalent interactions between carbohydrates and proteins play key roles in diverse biological events, including fertilization, cell–cell communication, host–pathogen interactions, immune response and cancer

(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

• proteins [5][6][7], cell–cell communication [8] and immune response to pathogens [7][9][10][11]. However, the application of oligosaccharides as potential therapeutic agents has its main drawback in the low instability of natural carbohydrates in biological systems. In addition, solid phase synthesis of