Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• -tuberculosis mycobacteria [42]; while antitumour [43] and antifouling [44] activities have also been published. Conclusion In summary, we report here the UHPLC–MS profiling of 39 Verongida sponge extracts from NatureBank, which led to large-scale extraction and mass-directed isolation studies on an Ianthella

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• new drugs to treat tuberculosis is also of interest. The starting point was probably CGI-17341 (20), a mutagenic compound reported by Ciba-Geigy in 1989 for its effect on mycobacteria [150]. And this substance owes its origin to the many nitroimidazole derivatives known for their anti-infective

• effects such as metronidazole (21), which is still used to treat anaerobic infections [151]. In any case, pretomanid (18), first mentioned in 1996 and reported [152] for its effect on mycobacteria growth in 2000, was developed by the TB alliance and approved for use in human in 2019. Again, this was the

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• α(1–6)-Man backbone, facilitating the deprotection and purification steps [157]. Naturally occurring mannosides, such as lipomannans found on the cell surface of mycobacteria, normally consist of a α(1–6)-mannan core substituted with α(1–2) branches, commonly introduced exploiting orthogonal PGs

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

• Rosana Ribić,
• Ranko Stojković,
• Lidija Milković,
• Mariastefania Antica,
• Marko Cigler and
• Srđanka Tomić

Beilstein J. Org. Chem. 2019, 15, 1805–1814, doi:10.3762/bjoc.15.174

• muramyl peptides induce significantly higher activation of NOD2 than MDP [29][30]. Mycobacteria present in complete Freund’s adjuvant, and related Actinomycetes, produce N-glycolyl MDP by the hydroxylase action on MDP (N-acetylmuramic acid within the peptidoglycan). The influence of structural

Synthesis and biological activity of methylated derivatives of the Pseudomonas metabolites HHQ, HQNO and PQS

• Sven Thierbach,
• Max Wienhold,
• Susanne Fetzner and
• Ulrich Hennecke

Beilstein J. Org. Chem. 2019, 15, 187–193, doi:10.3762/bjoc.15.18

• cytochromes in Mycobacteria than HQNO and therefore the methylation of HQNO can be seen as detoxification strategy [16]. Considering the natural occurrence of N- as well as O-methylated AQs in plants and the use of methylation of HQNO in Mycobacteria as detoxification reaction, we decided to investigate the

Lectins of Mycobacterium tuberculosis – rarely studied proteins

• Katharina Kolbe,
• Sri Kumar Veleti,
• Norbert Reiling and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

• ). In this paper we review previous studies on the carbohydrate-binding characteristics of mycobacteria and related Mtb proteins, discussing their potential relevance to Mtb infection and pathogenesis. Keywords: adhesion; carbohydrates; fimbriae; lectins; Mycobacterium tuberculosis; pili; Introduction

• has already been studied and reviewed in detail [21][39], we focus this review on the rarely studied mycobacterial lectins and their roles in recognizing glycosides on the surfaces of host immune and epithelial cells. Review Glycosides on the surfaces of mycobacteria and their host cell Eukaryotic

• )-branched α-D-arabinofuranoside-containing polymers [52]. LAM can further be peripherally modified, also known as ”capping“, the nature of which differs between mycobacterial species. In pathogenic mycobacteria, such as Mtb, LAM is capped to various degrees with one to three α-D-mannopyranosides [53], while

The design and synthesis of an antibacterial phenothiazine–siderophore conjugate

• Abed Tarapdar,
• James K. S. Norris,
• Oliver Sampson,
• Galina Mukamolova and
• James T. Hodgkinson

Beilstein J. Org. Chem. 2018, 14, 2646–2650, doi:10.3762/bjoc.14.242

• azotochelin. Catechol-based siderophores can act as xenosiderophores and be recognised for uptake by Gram-negative bacteria and mycobacteria [14][15]. Most commonly benzyl protecting groups are used in the synthesis of catechol siderophores and cleaved in the final step by palladium catalysed hydrogenation

• antibiotic delivery. A library of mono-, bis- and tris-catechol phenothiazine–siderophore conjugates are currently being prepared using this route. Their synthesis and MIC values against pathogenic mycobacteria, Gram-negative bacteria and Gram-positive bacteria, along with compound 11, will be reported in

Mechanochemistry of nucleosides, nucleotides and related materials

• Olga Eguaogie,
• Joseph S. Vyle,
• Patrick F. Conlon,
• Manuela A. Gîlea and
• Yipei Liang

Beilstein J. Org. Chem. 2018, 14, 955–970, doi:10.3762/bjoc.14.81

• grinding stones (15–20 mm in diameter), 100 g of dried tissue powder and petroleum ether (200–450 mL) [73][74][75]. As early as 1903, low temperature grinding was applied to disrupting refractory mycobacteria (using zirconia components under cooling in liquid air) [76] and subsequently mechanised using a

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

• extracellular mycobacteria are observed in all, the early, the pre-ulcerative and the ulcerative disease stage without being accompanied by granuloma formation [5]. The ulcers expand over time and can spread over the entire extremities. However, ulceration is normally not accompanied by pain and fever although

• all patients that distinctly differed from tuberculosis. However, the germ gave the typical acid-fast stain common to all mycobacteria. As reported by Fenner et al., MacCallum later suggested the name Mycobacterium ulcerans [17]. Initial attempts to cultivate the bacterium failed until it was realized

• (mycolactones C (2), D (3), E (6) and its minor oxo-metabolite (7), F (8) and dia-F (9), S1 (4) and S2 (5)) (Figure 2) were discovered in extracts from different M. ulcerans strains and closely related mycobacteria. Given their close genetic relationship [44], it has been suggested that all currently known

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

• Darcy J. Atkinson,
• Briar J. Naysmith,
• Daniel P. Furkert and
• Margaret A. Brimble

Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226

• fermentation industrially and is used as an antibiotic feed additive for pigs [26] and chickens [27] under the trade name enradin®. Minosaminomycin Minosaminomycin (9, Figure 3) was isolated in 1974 from a culture broth of Streptomyces MA514-A1 [28]. It was found to be active against Mycobacteria (M. smegmatis

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

• Guozheng Huang,
• Simon Schramm,
• Jörg Heilmann,
• David Biedermann,
• Vladimír Křen and
• Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

• (kernels) of H. wightiana, contains besides hydnocarpin mainly cyclopentenoic fatty acids [16], which show pronounced antibiotic activity and inhibit multiplication of mycobacteria [17]. Combination of these antibiotics together with hydnocarpin (MDR inhibitor) helped to treat such a persistent disease

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

• Shino Manabe and
• Yukishige Ito

Beilstein J. Org. Chem. 2016, 12, 328–333, doi:10.3762/bjoc.12.35

• occurrence of multiple-drug-resistant (MDR), extensive-drug-resistant (EDR), and totally drug-resistant (TDR) pathogens has increased the need for new drug candidates for treating tuberculosis. Mycothiol (MSH) 1 is the main low-molecular-weight thiol found in most actinomycetes, including Mycobacteria and

• mycobacteria for protection against foreign electrophilic agents such as oxidants, radicals, and drugs. In the detoxification pathway, MSH reacts with alkylating reagents and the resulting S-conjugates are subsequently cleaved at the amide bond by MSH S-conjugate amidase (Scheme 1) [4][5][6][7][8][9][10

Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals

• Éva Rajnavölgyi,
• Renáta Laczik,
• Viktor Kun,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

• depends on the type, number and position of the substituents [18][19]. For example, water soluble palmitic acid and myristic acid complexed by RAMEB could be used for cultivation of otherwise non-cultivable leprosy-derived psychrophilic mycobacteria [20]. The methylated β-CDs are used as cholesterol

The volatiles of pathogenic and nonpathogenic mycobacteria and related bacteria

• Thorben Nawrath,
• Georgies F. Mgode,
• Bart Weetjens,
• Stefan H. E. Kaufmann and
• Stefan Schulz

Beilstein J. Org. Chem. 2012, 8, 290–299, doi:10.3762/bjoc.8.31

• mycobacteria, as well as by mycobacteria-related Nocardia spp., were analyzed. Bacteria were cultivated on solid and in liquid media, and headspace samples were collected at various times during the bacterial lifecycle to elucidate the conditions giving optimal volatile emission. Emitted volatiles were

• fatty-acid derivatives were released by pathogenic/nonpathogenic mycobacteria, while the two Nocardia spp. (N. asteroides and N. africana) emitted the sesquiterpene aciphyllene. Pathogenic Mycobacterium tuberculosis strains grown on agar plates produced a distinct bouquet with different volatiles, while

• liquid cultures produce less compounds but sometimes an earlier onset of volatile production because of their steeper growth curves under this conditions. This behavior differentiates M. tuberculosis from other mycobacteria, which generally produced fewer compounds in seemingly lower amounts. Knowledge

Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• of a 3,4-butanediacetal-protected mannoside. The azidooctyl groups of these synthetic mannans were elaborated to fluorescent glycoconjugates and squaric ester derivatives useful for further conjugation studies. Keywords: fluorescently-labelled sugars; glycoconjugates; lipomannan; mycobacteria

• cell wall biosynthesis (e.g., thiacetazone, isoniazid, ethambutol, pyrazinamide, and ethionamide) with the cell wall of the tubercule bacillus being widely agreed as a promising target for new drugs [4][5]. The cell wall of all mycobacteria is especially rich in lipids and polysaccharides, with the

• group. Chemical structures of (A) a representative PIM, AcPIM5 and (B) a mannan fragment of LM from mycobacteria. Boxes denote the relationship of PIMs and LM to trisaccharide fragments synthesized in this study. Target di- and trisaccharide glycoconjugate fragments of PIMs and LM. ORTEP plot of single