Asymmetric Synthesis of &amp;#945;-Unsubstituted &amp;#946;-Hydroxy Acids

Alberício, Fernando

doi:10.2174/157017908784221558

Cited by 11 publications

(4 citation statements)

References 84 publications

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“…Several synthetic methodology precedents for the preparation of β-hydroxyalkanoic acids have been reported in the literature due to the ubiquity of this lipid moiety in biomolecules found in Gram negative bacterial cell walls . Access to optically pure β-hydroxyalkanoic acids is afforded by stereoselective reduction of the β-ketoalkanoic esters using Noyori’s catalytic hydrogenation, resolving agents of racemic mixtures, enzymatic reduction, , and recently, the exploitation of Mitsunobu chemistry . In our approach, the lipid units are prepared as racemic mixtures of benzyl β-hydroxyalkanoic esters in two steps: formation of the benzyl β-keto ester using Meldrum’s acid carbonyl chemistry − and reduction of the keto group with NaBH 3 CN under acidic conditions as shown in Scheme .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Four Diastereomers of Monorhamnolipids

et al. 2017

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Rhamnolipids are amphiphilic glycolipids biosynthesized by bacteria that, due to their low toxicity and biodegradability, are potential replacements for synthetic surfactants. The previously limited access to pure materials at the gram scale has hindered extensive characterization of rhamnolipid structure-performance behavior. Here, we present an efficient and versatile synthetic methodology from which four diastereomers of the most common monorhamnolipid, α-rhamnopyranosyl-β-hydroxydecanoyl-β-hydroxydecanoate, are prepared and subsequently characterized. Exploration of their behavior at the air-water interface is reported and analyzed in terms of the absolute configuration of the lipid tail carbinols at pH 4.0 and 8.0. All diastereomers exhibit a minimum surface tension of about 28 mN/m without a significant difference between the protonated (nonionic) or deprotonated (anionic) states. At pH 4.0 (nonionic), all diastereomers have a critical micelle concentration (CMC) in the micromolar range. At pH 8.0 (anionic), CMC values for the (R,R), (S,S), and (S,R) diastereomers are approximately an order of magnitude higher than in their nonionic states, whereas the (R,S) diastereomer exhibits a CMC about five times larger.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Four Diastereomers of Monorhamnolipids

et al. 2017

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“…β‐hydroxy acids or 3‐hydroxy carboxylic acids can be synthesised through various reactions. Spengler and Alberico (2013) [49] reviewed some of the reactions to yield α‐unsubstituted‐β‐hydroxy acids. This review focuses on the synthesis of β‐hydroxy acids as a moiety of depsipeptides and cyclodepsipeptides.…”

Section: Chemical Synthesis Of Precursor Cyclodepsipeptidesmentioning

confidence: 99%

An Overview of the Synthesis of Biologically Active Cyclodepsipeptides

et al. 2022

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Cyclodepsipeptide are a class of natural cyclic peptides that have a wide range of biological activities, hence the potential to be developed as new drug candidates. Cyclodpesipeptides comprise a backbone of amide bonds and at least one ester moiety, thus are complex and challenging to synthesis. Generally, cyclodepsipeptides are synthesised via solid‐phase peptide synthesis, solution‐phase or a combination of solid and solution‐phase. Currently, solid‐phase peptide synthesis is more in demand, but it also has several challenges in its application especially for the cyclodepsipeptide that contains N‐methylated residues, as well as solution‐phase peptide synthesis tends to have a longer reaction step. Therefore, the combination of solid and solution‐phase peptide synthesis is a better alternative. This review discusses the synthetic strategies for cyclodepsipeptides including the preparation of precursor and macrocyclization.

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“…The different reported strategies are listed below and illustrated with a few examples. This section is not exhaustive as other reviews have already been dedicated to this topic …”

Section: Fahfas Are Endogenous Lipidsmentioning

confidence: 99%

Branched Fatty Acyl Esters of Hydroxyl Fatty Acids (FAHFAs), Appealing Beneficial Endogenous Fat against Obesity and Type‐2 Diabetes

Balas

Feillet‐Coudray

Durand

2018

Chemistry A European J

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After a brief overview of the biological significance of FAHFAs, the present Minireview highlights the different strategies developed for their chemical syntheses. The term "FAHFAs" has been introduced in 2014 for fatty acyl esters of hydroxyl fatty acids, found in adipocytes, with antidiabetic properties. However, many other natural products contain this type of branched lipids in their structure. This review was then extended to the synthesis of these subunits, even though the length of the lipid chains and the location of the ester linkages are different, since the developed strategies may be applied to the synthesis of "FAHFA".

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Asymmetric Synthesis of α-Unsubstituted β-Hydroxy Acids

Cited by 11 publications

References 84 publications

Synthesis and Characterization of Four Diastereomers of Monorhamnolipids

Synthesis and Characterization of Four Diastereomers of Monorhamnolipids

An Overview of the Synthesis of Biologically Active Cyclodepsipeptides

Branched Fatty Acyl Esters of Hydroxyl Fatty Acids (FAHFAs), Appealing Beneficial Endogenous Fat against Obesity and Type‐2 Diabetes

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