scholarly journals Chemoenzymatic Synthesis of the Antifungal Compound (-)-Pestynol by a Convergent, Sonogashira Construction of the Central Yne-Diene

2018 ◽  
Vol 2019 (1) ◽  
pp. 77-79 ◽  
Author(s):  
Suresh Borra ◽  
Manoj Kumar ◽  
James McNulty ◽  
Daler Baidilov ◽  
Tomas Hudlicky
2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.


Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1040
Author(s):  
Asuka Shirakawa ◽  
Yoshiyuki Manabe ◽  
Koichi Fukase

Asparagine-linked N-glycans on proteins have diverse structures, and their functions vary according to their structures. In recent years, it has become possible to obtain high quantities of N-glycans via isolation and chemical/enzymatic/chemoenzymatic synthesis. This has allowed for progress in the elucidation of N-glycan functions at the molecular level. Interaction analyses with lectins by glycan arrays or nuclear magnetic resonance (NMR) using various N-glycans have revealed the molecular basis for the recognition of complex structures of N-glycans. Preparation of proteins modified with homogeneous N-glycans revealed the influence of N-glycan modifications on protein functions. Furthermore, N-glycans have potential applications in drug development. This review discusses recent advances in the chemical biology of N-glycans.


2021 ◽  
Vol 22 (2) ◽  
pp. 483
Author(s):  
Marija Ivanov ◽  
Abhilash Kannan ◽  
Dejan S. Stojković ◽  
Jasmina Glamočlija ◽  
Ricardo C. Calhelha ◽  
...  

Candidaalbicans represents one of the most common fungal pathogens. Due to its increasing incidence and the poor efficacy of available antifungals, finding novel antifungal molecules is of great importance. Camphor and eucalyptol are bioactive terpenoid plant constituents and their antifungal properties have been explored previously. In this study, we examined their ability to inhibit the growth of different Candida species in suspension and biofilm, to block hyphal transition along with their impact on genes encoding for efflux pumps (CDR1 and CDR2), ergosterol biosynthesis (ERG11), and cytotoxicity to primary liver cells. Camphor showed excellent antifungal activity with a minimal inhibitory concentration of 0.125–0.35 mg/mL while eucalyptol was active in the range of 2–23 mg/mL. The results showed camphor’s potential to reduce fungal virulence traits, that is, biofilm establishment and hyphae formation. On the other hand, camphor and eucalyptol treatments upregulated CDR1;CDR2 was positively regulated after eucalyptol application while camphor downregulated it. Neither had an impact on ERG11 expression. The beneficial antifungal activities of camphor were achieved with an amount that was non-toxic to porcine liver cells, making it a promising antifungal compound for future development. The antifungal concentration of eucalyptol caused cytotoxic effects and increased expression of efflux pump genes, which suggests that it is an unsuitable antifungal candidate.


2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Shabnam Javed ◽  
Zaid Mahmood ◽  
Khalid Mohammed Khan ◽  
Satyajit D. Sarker ◽  
Arshad Javaid ◽  
...  

AbstractAntifungal activity of Monothecabuxifolia methanolic extract and its various fractions were assessed against Macrophominaphaseolina, a soil-borne fungal pathogen of more than 500 vegetal species as well as rare and emerging opportunistic human pathogen. Different concentrations of methanolic extract (3.125 to 200 mg mL−1) inhibited fungal biomass by 39–45%. Isolated n-hexane, chloroform and ethyl acetate fractions suppressed fungal biomass by 32–52%, 29–50% and 29–35%, respectively. Triterpenes lupeol and lupeol acetate (1, 2) were isolated from n-hexane while betulin, β-sitosterol, β-amyrin, oleanolic acid (3–6) were isolated from chloroform fraction. Vanillic acid, protocatechuic acid, kaempferol and quercetin (7–10) were isolated from the ethyl acetate fraction and identified using various spectroscopic techniques namely mass spectroscopy and NMR. Antifungal activity of different concentrations (0.0312 to 2 mg mL−1) of the isolated compounds was evaluated and compared with the activity of a broad spectrum fungicide mancozeb. Different concentrations of mencozeb reduced fungal biomass by 83–85%. Among the isolated compounds lupeol acetate (2) was found the highest antifungal against M.phaseolina followed by betulin (3), vanillic acid (7), protocatechuic acid (8), β-amyrin (5) and oleanolic acid (6) resulting in 79–81%, 77–79%, 74–79%, 67–72%, 68–71% and 68–71%, respectively. Rest of the compounds also showed considerable antifungal activity and reduced M.phaseolina biomass by 41–64%.


2020 ◽  
Vol 59 (45) ◽  
pp. 19825-19829
Author(s):  
Jiabin Zhang ◽  
Ding Liu ◽  
Varma Saikam ◽  
Madhusudhan R. Gadi ◽  
Christopher Gibbons ◽  
...  

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