Synthesis of new chiral ionic liquids from α-hydroxycarboxylic acids

Poterała, Marcin; Plenkiewicz, Jan

doi:10.1016/j.tetasy.2011.01.024

Cited by 17 publications

(16 citation statements)

References 32 publications

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“…The α-hydroxy carboxylic acid 4 was prepared from L-isoleucine by published protocol. 42 The esterification of N -Boc- O -Me-tyrosine with acid 4 provided ester 5 in 96% yield by Mitsunobu reaction (Ph 3 P/DEAD). 43 The Boc group of ester 5 was removed using 4 M HCl in ethyl acetate.…”

Section: Resultsmentioning

confidence: 99%

Apratyramide, a Marine-Derived Peptidic Stimulator of VEGF-A and Other Growth Factors with Potential Application in Wound Healing

Cai¹,

Salvador‐Reyes

Zhang

et al. 2017

ACS Chem. Biol.

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A novel linear depsipeptide enriched with tyrosine-derived moieties, termed apratyramide, was isolated from an apratoxin-producing cyanobacterium. The structure was determined using a combination of NMR spectroscopy, mass spectrometry, and chiral analysis of the acid hydrolyzate and confirmed by total synthesis. Apratyramide up-regulated multiple growth factors at the transcript level in human keratinocyte (HaCaT) cells and induced the secretion of vascular endothelial growth factor A (VEGF-A) from HaCaT cells, suggesting the compound's potential wound-healing properties through growth factor induction. Transcriptome analysis and sequential validation supported the hypothesis and indicated its mode of action (MOA) through the unfolded protein response (UPR) pathway, which is functionally related to wound healing and angiogenesis. The conditioned medium of HaCaT cells treated with apratyramide induced angiogenesis in vitro. An ex vivo rabbit corneal epithelial model was applied to confirm the VEGF-A induction in this wound-healing model.

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Section: Resultsmentioning

confidence: 99%

Apratyramide, a Marine-Derived Peptidic Stimulator of VEGF-A and Other Growth Factors with Potential Application in Wound Healing

Cai¹,

Salvador‐Reyes

Zhang

et al. 2017

ACS Chem. Biol.

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“…ILA was synthesized from L-Ile as described by Poterała and Plenkiewicz (2011). SAG for establishing the standard curve in HPLC analyses was kindly provided by Shigeo Tanaka (Tanaka et al, 1990).…”

Section: Chemicalsmentioning

confidence: 99%

Novel Plant Immune-Priming Compounds Identified via High-Throughput Chemical Screening Target Salicylic Acid Glucosyltransferases in Arabidopsis

et al. 2012

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Plant activators are compounds, such as analogs of the defense hormone salicylic acid (SA), that protect plants from pathogens by activating the plant immune system. Although some plant activators have been widely used in agriculture, the molecular mechanisms of immune induction are largely unknown. Using a newly established high-throughput screening procedure that screens for compounds that specifically potentiate pathogen-activated cell death in Arabidopsis thaliana cultured suspension cells, we identified five compounds that prime the immune response. These compounds enhanced disease resistance against pathogenic Pseudomonas bacteria in Arabidopsis plants. Pretreatments increased the accumulation of endogenous SA, but reduced its metabolite, SA-O-β-d-glucoside. Inducing compounds inhibited two SA glucosyltransferases (SAGTs) in vitro. Double knockout plants that lack both SAGTs consistently exhibited enhanced disease resistance. Our results demonstrate that manipulation of the active free SA pool via SA-inactivating enzymes can be a useful strategy for fortifying plant disease resistance and may identify useful crop protectants.

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“…CILs can also act as a tool for organizing the structure of solid polymeric electrolytes (SPE), playing the triple role as plasticizer, solvent for the ions, and medium. Most of the described optically active ILs are prepared from easily accessible natural chiral substrates [40]. The use of ILs in so-called “green chemistry”, as for example solvents in inorganic or organic syntheses or as a replacement for many hazardous and volatile organic solvents, raises the question about the toxicity of newly designed compounds.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

Borowiecki¹,

Milner-Krawczyk²,

Plenkiewicz³

2013

Beilstein J. Org. Chem.

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SummaryRacemic 1-(β-hydroxypropyl)azoles were prepared by solvent-free direct regioselective ring opening of 1,2-propylene oxide with imidazole or 1,2,4-triazole. Lipase-catalyzed transesterification of alcohols with vinyl acetate resulted in kinetic enantiomers resolution. Separated (S)-enantiomers of (+)-1-(1H-imidazol-1-yl)propan-2-ol and (+)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol were quaternized with alkyl bromides or iodides, yielding novel optically active ionic liquids. Racemic salts were tested against a wide range of microorganisms.

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Synthesis of new chiral ionic liquids from α-hydroxycarboxylic acids

Cited by 17 publications

References 32 publications

Apratyramide, a Marine-Derived Peptidic Stimulator of VEGF-A and Other Growth Factors with Potential Application in Wound Healing

Apratyramide, a Marine-Derived Peptidic Stimulator of VEGF-A and Other Growth Factors with Potential Application in Wound Healing

Novel Plant Immune-Priming Compounds Identified via High-Throughput Chemical Screening Target Salicylic Acid Glucosyltransferases in Arabidopsis

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

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