Oligonucleotide analogues with cationic backbone linkages

• Melissa Meng and
• Christian Ducho

Beilstein J. Org. Chem. 2018, 14, 1293–1308, doi:10.3762/bjoc.14.111

• ' (Figure 5) [72][73][74]. In principle, the NAA-modification is inspired by 'high-carbon' nucleoside structures (i.e., nucleosides having more than five carbon atoms in the sugar unit) found in naturally occurring nucleoside antibiotics [75][76][77]. In muraymycin- and caprazamycin-type nucleoside

• antibiotics, among others, such 'high-carbon' nucleosides are uridine-derived amino acid structures ('glycyluridine', GlyU) [78][79][80], which are aminoribosylated at the 5'-hydroxy group. As part of our ongoing research program on muraymycin nucleoside antibiotics (e.g., muraymycin A1 (44)) and their

Synthesis of the C8’-epimeric thymine pyranosyl amino acid core of amipurimycin

• Pramod R. Markad,
• Navanath Kumbhar and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2016, 12, 1765–1771, doi:10.3762/bjoc.12.165

• ; carbohydrate; peptidyl nucleosides; Introduction Peptidyl nucleoside antibiotics are a class of complex molecules that encompass an extensive array of natural products [1]. The notable structural features of peptidyl nucleosides are responsible for their miscellaneous biological activities such as antitumor

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• replication and folate metabolism [21]. Promising candidates meeting the requirements for new drugs are nucleoside antibiotics, i.e., uridine-derived compounds that address the enzyme translocase I (MraY) as a novel target, thereby interfering with a membrane-associated intracellular step of peptidoglycan

• biosynthesis. This review will focus on muraymycins as a subclass of nucleoside antibiotics, covering their mode of action, synthetic approaches as well as SAR studies on several derivatives. Furthermore, first insights into the biosynthesis of these Streptomyces-produced secondary metabolites will be

• discussed. Review Structures of naturally occurring muraymycins The muraymycins were first isolated in 2002 from a broth of a Streptomyces sp. [22]. McDonald et al. discovered and characterised 19 naturally occurring muraymycins (Figure 1). These compounds belong to the family of nucleoside antibiotics

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• . Biochemical properties of the novel nucleoside analogs are also presented (if provided by the authors). Keywords: multicomponent reaction; nucleoside analog; nucleoside antibiotics; nucleoside construction; nucleoside modification; Introduction Chemical modifications of natural ribose or 2'-deoxyribose

Amino acid motifs in natural products: synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine

• Oliver Ries,
• Martin Büschleb,
• Markus Granitzka,
• Dietmar Stalke and
• Christian Ducho

Beilstein J. Org. Chem. 2014, 10, 1135–1142, doi:10.3762/bjoc.10.113

• . Within the context of our work regarding the total synthesis of muraymycin nucleoside antibiotics, we have developed a synthetic approach towards (2S,3S)-3-hydroxyleucine building blocks. Application of different protecting group patterns led to building blocks suitable for C- or N-terminal

• ], as monosulfuric acid ester [6] or as potential acylation site for fatty acid side chains such as in A- and B-series muraymycin nucleoside antibiotics (Figure 1) [7][8][9]. In the case of these muraymycin congeners, acylation of the 3-hydroxy position with fatty acid side chains, which are ω

• -phase peptide synthesis (SPPS). Furthermore, we have employed such building blocks for the synthesis of protected analogues 15a,b of the tripeptide unit of naturally occurring muraymycin nucleoside antibiotics. We have also established unprecedented protocols for early- and late-stage derivatizations of

(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

• derivatives with tendency to adopt specific compact conformations (foldamers). Linear naturally-occurring SAA homo-oligomers SAAs occur extensively in nature as subunits of oligosaccharides in cell walls such as N-acetylneuraminic 1 and muramic acids 2, as well as in some nucleoside antibiotics (e.g