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Article ; Online: Iron oxide-promoted photochemical oxygen reduction to hydrogen peroxide (H

Freese, Thomas / Meijer, Jelmer T / Brands, Maria B / Alachouzos, Georgios / Stuart, Marc C A / Tarozo, Rafael / Gerlach, Dominic / Smits, Joost / Rudolf, Petra / Reek, Joost N H / Feringa, Ben L

EES catalysis

2023 Volume 2, Issue 1, Page(s) 262–275

Abstract: Hydrogen peroxide ( ... ...

Abstract	Hydrogen peroxide (H
Language	English
Publishing date	2023-11-24
Publishing country	England
Document type	Journal Article
ISSN	2753-801X
ISSN (online)	2753-801X
DOI	10.1039/d3ey00256j
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Purification of omega-3 polyunsaturated fatty acids from fish oil using silver-thiolate chromatographic material and high performance liquid chromatography.

Dillon, James T / Aponte, José C / Tarozo, Rafael / Huang, Yongsong

Journal of chromatography. A

2013 Volume 1312, Page(s) 18–25

Abstract: Omega-3 polyunsaturated fatty acids (ω-3 PUFAs) have become increasingly popular in dietary supplements worldwide and global demand for higher purity ω-3 PUFAs in clinical applications has been rising rapidly in the recent years. Traditional methods for ... ...

Abstract	Omega-3 polyunsaturated fatty acids (ω-3 PUFAs) have become increasingly popular in dietary supplements worldwide and global demand for higher purity ω-3 PUFAs in clinical applications has been rising rapidly in the recent years. Traditional methods for isolating ω-3 PUFAs however, generally require multiple, cumbersome steps to obtain high purity (>95%) products. In this study, we report an efficient liquid chromatography method for purifying individual omega-3 fatty acid ethyl esters (FAEEs), eicosapentaenoic acid (EPA, C20:5) and docosahexaenoic acid (DHA, C22:6), at >95% purity using a silver(I)-mercaptopropyl stationary phase, otherwise known as silver-thiolate chromatographic material (AgTCM). We demonstrate the key variables controlling separation of FAEEs with a silver(I)-thiolate stationary phase and examine important similarities and differences between silver-thiolate and silver-ion chromatography in regards to the separation mechanism taking place. We demonstrate the separation behavior of FAEEs under various conditions such as mobile phase composition, flow rate and sample injection amount. Purification of EPA and DHA was carried out on an analytical and semi-preparative scale and the resulting purity was determined by GC-FID. We report high attainable purity for EPA (>95%) and DHA (>99%) from a single isocratic separation of fish oil FAEEs within 5-10min using a mobile phase of heptane/acetone (95:5, % v/v).
MeSH term(s)	Chromatography, High Pressure Liquid/methods ; Dietary Supplements/analysis ; Fatty Acids, Omega-3/analysis ; Fatty Acids, Omega-3/chemistry ; Fatty Acids, Omega-3/isolation & purification ; Fish Oils/chemistry ; Silver/chemistry ; Sulfhydryl Compounds/chemistry
Chemical Substances	Fatty Acids, Omega-3 ; Fish Oils ; Sulfhydryl Compounds ; Silver (3M4G523W1G)
Language	English
Publishing date	2013-10-18
Publishing country	Netherlands
Document type	Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	1171488-8
ISSN	1873-3778 ; 0021-9673
ISSN (online)	1873-3778
ISSN	0021-9673
DOI	10.1016/j.chroma.2013.08.064
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Article ; Online: Efficient liquid chromatographic analysis of mono-, di-, and triglycerols using silver thiolate stationary phase.

Dillon, James T / Aponte, José C / Tarozo, Rafael / Huang, Yongsong

Journal of chromatography. A

2012 Volume 1240, Page(s) 90–95

Abstract: We show that the characterization of mono-, di- and triglycerols can be readily accomplished by high performance liquid chromatography (HPLC) with silver(I)-mercaptopropyl modified silica gel, or silver thiolate chromatographic material (AgTCM), which ... ...

Abstract	We show that the characterization of mono-, di- and triglycerols can be readily accomplished by high performance liquid chromatography (HPLC) with silver(I)-mercaptopropyl modified silica gel, or silver thiolate chromatographic material (AgTCM), which can be used with evaporative light scattering detection (ELSD) or atmospheric pressure chemical ionization mass spectroscopy (APCI-MS). Separation of triglycerols varying by degrees of unsaturation and cis/trans configuration in common oil samples can be achieved using a simple linear gradient of hexane and acetone. In addition to double bonds, AgTCM also displays major selectivity for compounds with different levels of polarity, allowing for efficient separation between mono-, di- and triglycerols. In comparison to conventional reversed phase columns, AgTCM produces simple chromatograms for rapid assessment of degrees of unsaturation and the amount of trans fats in triglycerides, which are central issues to food quality determination. In comparison to previous silver-ion based HPLC separations, AgTCM-HPLC based column offers greatly enhanced stability, inertness, durability, and reproducibility allowing routine coupling of the HPLC with a mass spectrometer for detection.
MeSH term(s)	Acetone/chemistry ; Chromatography, High Pressure Liquid/instrumentation ; Chromatography, High Pressure Liquid/methods ; Dietary Fats/analysis ; Dietary Fats/isolation & purification ; Glycerides/analysis ; Glycerides/isolation & purification ; Hexanes/chemistry ; Plant Oils/analysis ; Plant Oils/isolation & purification ; Reproducibility of Results ; Silver/chemistry ; Sulfhydryl Compounds/chemistry
Chemical Substances	Dietary Fats ; Glycerides ; Hexanes ; Plant Oils ; Sulfhydryl Compounds ; Acetone (1364PS73AF) ; Silver (3M4G523W1G)
Language	English
Publishing date	2012-06-01
Publishing country	Netherlands
Document type	Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	1171488-8
ISSN	1873-3778 ; 0021-9673
ISSN (online)	1873-3778
ISSN	0021-9673
DOI	10.1016/j.chroma.2012.03.083
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Separation of unsaturated organic compounds using silver-thiolate chromatographic material.

Aponte, José C / Dillon, James T / Tarozo, Rafael / Huang, Yongsong

Journal of chromatography. A

2012 Volume 1240, Page(s) 83–89

Abstract: Separation of organic compounds containing various numbers of double bonds (DB) can be readily achieved by using silver ion impregnated silica gel, often called silver-ion or argentation chromatography. However, the practical application of silver-ion ... ...

Abstract	Separation of organic compounds containing various numbers of double bonds (DB) can be readily achieved by using silver ion impregnated silica gel, often called silver-ion or argentation chromatography. However, the practical application of silver-ion liquid chromatography in analytical and preparative separations has been limited by the concerns about the stability and mobility of silver ions and the widespread use of reversed phase high performance liquid chromatography. Silver covalently anchored onto the thiol moiety of mercaptopropyl modified silica gel has been tested for the separation of polycyclic aromatic hydrocarbons by ring numbers, but has never been shown to separate mixtures of alkenes having different number of double bonds. We report here that silver-thiolate chromatographic material (AgTCM; including, but not limited to, silver(I) mercaptopropyl silica gel) is also highly efficient in liquid chromatographic separation of alkane/alkenes differing by one double bond. AgTCM displays exceptionally high selectivity for unsaturated compounds and high stability under extended heat and light exposure, while silver is virtually immobile during solvent elution. Compared to ionic silver, silver-thiolate interacts with double bonds less strongly, allowing AgTCM to efficiently separate olefins using less polar (and often less viscous and lower cost) solvents. The interaction energy between silver and ethylene is calculated using established computational methods and the results are in full agreement with our experimental results. Importantly, the exceptional stability of AgTCM gives rise to much higher compound recovery than conventional silver-ion silica gel during the chromatographic elution. Our results pave the way for the development of novel covalently bonded, transition metal-containing chromatographic materials.
MeSH term(s)	Alkenes/chemistry ; Alkenes/isolation & purification ; Chromatography, Liquid/instrumentation ; Chromatography, Liquid/methods ; Molecular Conformation ; Silver/chemistry ; Sulfhydryl Compounds/chemistry ; Thermodynamics
Chemical Substances	Alkenes ; Sulfhydryl Compounds ; Silver (3M4G523W1G)
Language	English
Publishing date	2012-06-01
Publishing country	Netherlands
Document type	Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	1171488-8
ISSN	1873-3778 ; 0021-9673
ISSN (online)	1873-3778
ISSN	0021-9673
DOI	10.1016/j.chroma.2012.03.082
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: Purification of omega-3 polyunsaturated fatty acids from fish oil using silver-thiolate chromatographic material and high performance liquid chromatography

Dillon, James T / Aponte, José C / Tarozo, Rafael / Huang, Yongsong

Journal of chromatography. 2013 Oct. 18, v. 1312

2013

Abstract	Omega-3 polyunsaturated fatty acids (ω-3 PUFAs) have become increasingly popular in dietary supplements worldwide and global demand for higher purity ω-3 PUFAs in clinical applications has been rising rapidly in the recent years. Traditional methods for isolating ω-3 PUFAs however, generally require multiple, cumbersome steps to obtain high purity (>95%) products. In this study, we report an efficient liquid chromatography method for purifying individual omega-3 fatty acid ethyl esters (FAEEs), eicosapentaenoic acid (EPA, C20:5) and docosahexaenoic acid (DHA, C22:6), at >95% purity using a silver(I)-mercaptopropyl stationary phase, otherwise known as silver-thiolate chromatographic material (AgTCM). We demonstrate the key variables controlling separation of FAEEs with a silver(I)-thiolate stationary phase and examine important similarities and differences between silver-thiolate and silver-ion chromatography in regards to the separation mechanism taking place. We demonstrate the separation behavior of FAEEs under various conditions such as mobile phase composition, flow rate and sample injection amount. Purification of EPA and DHA was carried out on an analytical and semi-preparative scale and the resulting purity was determined by GC-FID. We report high attainable purity for EPA (>95%) and DHA (>99%) from a single isocratic separation of fish oil FAEEs within 5–10min using a mobile phase of heptane/acetone (95:5, % v/v).
Keywords	acetone ; dietary supplements ; docosahexaenoic acid ; eicosapentaenoic acid ; esters ; fish oils ; gas chromatography ; heptane ; high performance liquid chromatography ; omega-3 fatty acids ; silver
Language	English
Dates of publication	2013-1018
Size	p. 18-25.
Publishing place	Elsevier B.V.
Document type	Article
ZDB-ID	218139-3
ISSN	0021-9673 ; 0378-4355 ; 0376-737X
ISSN	0021-9673 ; 0378-4355 ; 0376-737X
DOI	10.1016/j.chroma.2013.08.064
Database	NAL-Catalogue (AGRICOLA)

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Article: Unprecedented separation of long chain alkenones from gas chromatography with a poly(trifluoropropylmethylsiloxane) stationary phase

Longo, William M / Dillon, James T / Tarozo, Rafael / Salacup, Jeffrey M / Huang, Yongsong

Organic geochemistry. 2013 Dec., v. 65

2013

Abstract: Long chain alkenones (LCAs) have played a central role in reconstructing paleo-sea surface temperature throughout much of the world oceans. The standard method for LCA separation and quantification utilizes gas chromatography (GC) with a non-polar column ...

Abstract	Long chain alkenones (LCAs) have played a central role in reconstructing paleo-sea surface temperature throughout much of the world oceans. The standard method for LCA separation and quantification utilizes gas chromatography (GC) with a non-polar column and flame ionization detection (FID). The method has remained nearly unchanged since the debut of alkenone paleothermometry over three decades ago. The conventional stationary phase used [poly(dimethylsiloxane)] is adequate for calculation of the U₃₇ ᴷ′ index for most marine samples, but performs poorly in the separation of methyl and ethyl C₃₈ LCAs and fails to separate certain lacustrine LCAs, including structural isomers featuring differing double bond and carbonyl positions. Here, we demonstrate major improvements in the selectivity and resolution of numerous LCAs using a mid-polarity, dipole selective poly(trifluoropropylmethylsiloxane) GC stationary phase with FID. Various columns featuring this phase achieved baseline resolution of all C₃₈ LCAs in a marine sediment and Emiliania huxleyi culture samples, improving peak resolution of C₃₈ LCAs by>350%. Such dipole selective stationary phases also reveal novel tri-unsaturated isomeric LCAs in lacustrine samples, for which we provide the first report and preliminary characterization. We conduct a thorough evaluation of LCA retention behavior on poly(trifluoropropylmethylsiloxane) and poly(dimethylsiloxane) columns and report an optimal range of operating conditions for both phases.
Keywords	Emiliania huxleyi ; flame ionization ; isomers ; marine sediments ; oceans ; surface temperature
Language	English
Dates of publication	2013-12
Size	p. 94-102.
Publishing place	Elsevier Ltd
Document type	Article
ISSN	0146-6380
DOI	10.1016/j.orggeochem.2013.10.011
Database	NAL-Catalogue (AGRICOLA)

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Article: Separation of unsaturated organic compounds using silver–thiolate chromatographic material

Aponte, José C / Dillon, James T / Tarozo, Rafael / Huang, Yongsong

Journal of chromatography. 2012 June 1, v. 1240

2012

Abstract	Separation of organic compounds containing various numbers of double bonds (DB) can be readily achieved by using silver ion impregnated silica gel, often called silver-ion or argentation chromatography. However, the practical application of silver-ion liquid chromatography in analytical and preparative separations has been limited by the concerns about the stability and mobility of silver ions and the widespread use of reversed phase high performance liquid chromatography. Silver covalently anchored onto the thiol moiety of mercaptopropyl modified silica gel has been tested for the separation of polycyclic aromatic hydrocarbons by ring numbers, but has never been shown to separate mixtures of alkenes having different number of double bonds. We report here that silver–thiolate chromatographic material (AgTCM; including, but not limited to, silver(I) mercaptopropyl silica gel) is also highly efficient in liquid chromatographic separation of alkane/alkenes differing by one double bond. AgTCM displays exceptionally high selectivity for unsaturated compounds and high stability under extended heat and light exposure, while silver is virtually immobile during solvent elution. Compared to ionic silver, silver–thiolate interacts with double bonds less strongly, allowing AgTCM to efficiently separate olefins using less polar (and often less viscous and lower cost) solvents. The interaction energy between silver and ethylene is calculated using established computational methods and the results are in full agreement with our experimental results. Importantly, the exceptional stability of AgTCM gives rise to much higher compound recovery than conventional silver-ion silica gel during the chromatographic elution. Our results pave the way for the development of novel covalently bonded, transition metal-containing chromatographic materials.
Keywords	alkanes ; energy ; ethylene ; heat ; ions ; polycyclic aromatic hydrocarbons ; reversed-phase high performance liquid chromatography ; silica gel ; silver ; solvents ; thiols
Language	English
Dates of publication	2012-0601
Size	p. 83-89.
Publishing place	Elsevier B.V.
Document type	Article
ZDB-ID	218139-3
ISSN	0021-9673 ; 0378-4355 ; 0376-737X
ISSN	0021-9673 ; 0378-4355 ; 0376-737X
DOI	10.1016/j.chroma.2012.03.082
Database	NAL-Catalogue (AGRICOLA)

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Article: Efficient liquid chromatographic analysis of mono-, di-, and triglycerols using silver thiolate stationary phase

Dillon, James T / Aponte, José C / Tarozo, Rafael / Huang, Yongsong

Journal of chromatography. 2012 June 1, v. 1240

2012

Abstract	We show that the characterization of mono-, di- and triglycerols can be readily accomplished by high performance liquid chromatography (HPLC) with silver(I)-mercaptopropyl modified silica gel, or silver thiolate chromatographic material (AgTCM), which can be used with evaporative light scattering detection (ELSD) or atmospheric pressure chemical ionization mass spectroscopy (APCI-MS). Separation of triglycerols varying by degrees of unsaturation and cis/trans configuration in common oil samples can be achieved using a simple linear gradient of hexane and acetone. In addition to double bonds, AgTCM also displays major selectivity for compounds with different levels of polarity, allowing for efficient separation between mono-, di- and triglycerols. In comparison to conventional reversed phase columns, AgTCM produces simple chromatograms for rapid assessment of degrees of unsaturation and the amount of trans fats in triglycerides, which are central issues to food quality determination. In comparison to previous silver-ion based HPLC separations, AgTCM–HPLC based column offers greatly enhanced stability, inertness, durability, and reproducibility allowing routine coupling of the HPLC with a mass spectrometer for detection.
Keywords	acetone ; atmospheric pressure ; durability ; food quality ; hexane ; high performance liquid chromatography ; ionization ; light scattering ; mass spectrometry ; oils ; rapid methods ; silica gel ; silver ; trans fatty acids ; triacylglycerols
Language	English
Dates of publication	2012-0601
Size	p. 90-95.
Publishing place	Elsevier B.V.
Document type	Article
ZDB-ID	218139-3
ISSN	0021-9673 ; 0378-4355 ; 0376-737X
ISSN	0021-9673 ; 0378-4355 ; 0376-737X
DOI	10.1016/j.chroma.2012.03.083
Database	NAL-Catalogue (AGRICOLA)

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Article: Polycyclic aromatic hydrocarbons (PAHs) in lake sediments record historic fire events: Validation using HPLC-fluorescence detection

Denis, Elizabeth H / Toney, Jaime L / Tarozo, Rafael / Scott Anderson, R / Roach, Lydia D / Huang, Yongsong

Organic geochemistry. 2012 Apr., v. 45

2012

Abstract: Understanding the natural mechanisms that control fire occurrence in terrigenous ecosystems requires long and continuous records of past fires. Proxies, such as sedimentary charcoal and tree-ring fire scars, have temporal or spatial limitations and do ... ...

Abstract	Understanding the natural mechanisms that control fire occurrence in terrigenous ecosystems requires long and continuous records of past fires. Proxies, such as sedimentary charcoal and tree-ring fire scars, have temporal or spatial limitations and do not directly detect fire intensity. We show in this study that polycyclic aromatic hydrocarbons (PAHs) produced during wildfires record local fire events and fire intensity. We demonstrate that high performance liquid chromatography with fluorescence detector (HPLC-FLD) is superior to gas chromatography–mass spectrometry (GC–MS) for detecting the low concentrations of sedimentary PAHs derived from natural fires. The HPLC-FLD is at least twice as sensitive as the GC–MS in selective ion monitoring (SIM) mode for parent PAHs and five times as sensitive for retene. The annual samples extracted from varved sediments from Swamp Lake in Yosemite National Park, California are compared with the observational fire history record and show that PAH fluxes record fires within 0.5km of the lake. The low molecular weight (LMW) PAHs (e.g., fluoranthene, pyrene and benz[a]anthracene) are the best recorders of fire, whereas the high molecular weight (HMW) PAHs likely record fire intensity. PAHs appear to resolve some of the issues inherent to other fire proxies, such as secondary deposition of charcoal. This study advances our understanding of how PAHs can be used as markers for fire events and poses new questions regarding the distribution of these compounds in the environment.
Keywords	anthracenes ; charcoal ; ecosystems ; fire intensity ; fire scars ; fluorescence ; gas chromatography-mass spectrometry ; growth rings ; high performance liquid chromatography ; lakes ; molecular weight ; monitoring ; national parks ; sediments ; swamps ; wildfires ; California
Language	English
Dates of publication	2012-04
Size	p. 7-17.
Publishing place	Elsevier Ltd
Document type	Article
ISSN	0146-6380
DOI	10.1016/j.orggeochem.2012.01.005
Database	NAL-Catalogue (AGRICOLA)

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Article: Origin and Evolution of Prebiotic Organic Matter As Inferred from the Tagish Lake Meteorite

Science. 2011 June 10, v. 332, no. 6035

2011

Abstract: The complex suite of organic materials in carbonaceous chondrite meteorites probably originally formed in the interstellar medium and/or the solar protoplanetary disk, but was subsequently modified in the meteorites' asteroidal parent bodies. The ... ...

Abstract	The complex suite of organic materials in carbonaceous chondrite meteorites probably originally formed in the interstellar medium and/or the solar protoplanetary disk, but was subsequently modified in the meteorites' asteroidal parent bodies. The mechanisms of formation and modification are still very poorly understood. We carried out a systematic study of variations in the mineralogy, petrology, and soluble and insoluble organic matter in distinct fragments of the Tagish Lake meteorite. The variations correlate with indicators of parent body aqueous alteration. At least some molecules of prebiotic importance formed during the alteration.
Keywords	lakes ; mineralogy ; organic matter ; prebiotics
Language	English
Dates of publication	2011-0610
Size	p. 1304-1307.
Publishing place	American Association for the Advancement of Science
Document type	Article
ZDB-ID	128410-1
ISSN	1095-9203 ; 0036-8075
ISSN (online)	1095-9203
ISSN	0036-8075
DOI	10.1126/science.1203290
Database	NAL-Catalogue (AGRICOLA)

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