126442-53-3

Upstream product

• 92144-04-2 1-<(tert-butyldimethylsilyl)oxy>-1-(benzyloxy)ethylene 
• 66-25-1 hexanal 
• 33796-86-0 (S)-3-hydroxyoctanoic acid 
• 44987-72-6 (R)-3-hydroxy-octanoic acid 
• 100-39-0 benzyl bromide 
• 78672-90-9 methyl (R)-(-)-3-hydroxydecanoate 
• 5163-67-7 (E)-oct-3-enoic acid 

Relevant academic research and scientific papers

Graphiumins, new thiodiketopiperazines from the marine-derived fungus Graphium sp. OPMF00224

Eight new thiodiketopiperazines, designated as graphiumins A to H (1-8), were isolated along with bisdethiobis(methylthio)-deacetylaranotin (9) and bisdethiobis(methylthio)-deacetylapoaranotin (10) from the culture broth of the marine-derived fungus Graph

Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans

Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 μg/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.

Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds

A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.87.0 mM and 0.16.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.

Total synthesis and structural validation of cyclodepsipeptides solonamide A and B

Microorganisms are an attractive source of new natural products with antimicrobial properties, and the marine environment constitutes a prolific resource of bioactive microorganisms. During a global research expedition (Galathea III), two depsipeptides, solonamide A and solonamide B, were isolated from the marine bacterium Photobacterium halotolerance and were found to inhibit virulence gene expression in the serious human pathogen, Staphylococcus aureus. They act by interfering with the agr quorum sensing system and show resemblance to the endogenous S. aureus quorum sensing peptide, autoinducing peptide I (AIP-I). To enable more comprehensive studies, we embarked on the chemical synthesis of solonamides A and B. The key synthetic steps were formation of the (R)-β-hydroxy-fatty-acids by stereo-selective aldol reactions and a cyclative macrolactamization, which proceeded under highly dilute conditions. Thus, the first total syntheses of the solonamides corroborated the originally assigned structures, and by changing the stereochemistry of the auxiliary in the aldol steps we gained access to the natural products as well as their β3-epimers.

Catalytic asymmetric hydroboration of β,γ-unsaturated Weinreb amides: Striking influence of the borane

Subtle differences in the structure of the borane strongly influence the catalytic efficiency and level of enantioselectivity in the catalytic asymmetric hydroboration of β,γ-unsaturated Weinreb amides.

ASYMMETRIC ALDOL-TYPE REACTION BETWEEN BOTH A CHIRAL KETENE SILYL ACETALS OF ACETIC ACID ESTERS AND ALDEHYDES BY USE OF A CHIRAL PROMOTER

Highly enantioselective aldol-type reaction between achiral ketene silyl acetals of acetic acid esters and achiral aldehydes is successfully carried out by the use of a chiral diamine coordinated tin (II) trifluoromethanesulfonate (tin (II) triflate) and tributyltin fluoride.The structure of this new promoter and the mechanism of the present asymmetric aldol-type reaction are discussed.

Asymmetric Aldol-type Reaction between Both Achiral Ketene Silyl Acetals and Aldehydes by the Use of a Chiral Promoter

Highly enantioselective aldol-type reaction of achiral ketene silyl acetals with achiral aldehydes is carried out by the use of a chiral promoter, a combined use of chiral diamine coordinated tin(II) triflate and tributyltin fluoride.