Development of an advanced derivatization protocol for the unambiguous identification of monosaccharides in complex mixtures by gas and liquid chromatography

Haas, Maren; Lamour, Saskia; Trapp, Oliver

doi:10.1016/j.chroma.2018.07.015

Cited by 37 publications

(37 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The formose reaction was stopped by adding citric acid and freezing the sample. After lyophilization, the sample was analyzed via gas chromatography in combination with a mass spectrometer, as described in the preceding studies by Haas et al [ 103 , 104 ] (abbreviated there as GC-MS).…”

Section: Methodsmentioning

confidence: 99%

Possible Ribose Synthesis in Carbonaceous Planetesimals

Paschek

Köhler

Pearce

et al. 2022

Life

Self Cite

View full text Add to dashboard Cite

The origin of life might be sparked by the polymerization of the first RNA molecules in Darwinian ponds during wet-dry cycles. The key life-building block ribose was found in carbonaceous chondrites. Its exogenous delivery onto the Hadean Earth could be a crucial step toward the emergence of the RNA world. Here, we investigate the formation of ribose through a simplified version of the formose reaction inside carbonaceous chondrite parent bodies. Following up on our previous studies regarding nucleobases with the same coupled physico-chemical model, we calculate the abundance of ribose within planetesimals of different sizes and heating histories. We perform laboratory experiments using catalysts present in carbonaceous chondrites to infer the yield of ribose among all pentoses (5Cs) forming during the formose reaction. These laboratory yields are used to tune our theoretical model that can only predict the total abundance of 5Cs. We found that the calculated abundances of ribose were similar to the ones measured in carbonaceous chondrites. We discuss the possibilities of chemical decomposition and preservation of ribose and derived constraints on time and location in planetesimals. In conclusion, the aqueous formose reaction might produce most of the ribose in carbonaceous chondrites. Together with our previous studies on nucleobases, we found that life-building blocks of the RNA world could be synthesized inside parent bodies and later delivered onto the early Earth.

show abstract

Section: Methodsmentioning

confidence: 99%

Possible Ribose Synthesis in Carbonaceous Planetesimals

Paschek

Köhler

Pearce

et al. 2022

Life

Self Cite

View full text Add to dashboard Cite

show abstract

“…Derivatization and analysis. Samples were derivatised as silylated oximes in a two-step procedure using O-ethyl hydroxylamine and N-/O-bistrifluoroacetamide with the internal standard phenyl-β-D-glucopyranoside following a previously described method 39 . Separation and analysis was performed by gas chromatography-mass spectrometry (GC-MS) on a SE-52 column (L = 14 m, ID = 250 µm, FT = 250 nm) using a Thermo Trace GC Ultra coupled to a flame ionisation detector and a PolarisQ mass spectrometer in electron impact mode (EI).…”

Section: Methodsmentioning

confidence: 99%

Mineral-mediated carbohydrate synthesis by mechanical forces in a primordial geochemical setting

et al. 2020

Self Cite

View full text Add to dashboard Cite

The formation of carbohydrates represents an essential step to provide building blocks and a source of chemical energy in several models for the emergence of life. Formaldehyde, glycolaldehyde and a basic catalyst are the initial components forming a variety of sugar molecules in the cascade-type multi-step formose reaction. While numerous side reactions and even deterioration can be observed in aqueous media, selective prebiotic sugar formation is feasible in solid-state, mechanochemical reactions and might have occurred in early geochemistry. However, the precise role of different basic catalysts and the influence of the atmospheric conditions in the solid-state formose reaction remain unknown. Here we show, that in a primordial scenario the mechanochemical formose reaction is capable to form monosaccharides with a broad variety of mineral classes as catalysts with only minute amounts of side products such as lactic acid or methanol, independent of the atmospheric conditions. The results give insight into recent findings of formose sugars on meteorites and offer a water-free and robust pathway for monosaccharides independent of the external conditions both for the early Earth or an extra-terrestrial setting.

show abstract

“…GC-MS detection of carbohydrates followed a published protocol [40]. In short: About 2 to 5 mg of the sample was dissolved in 200 µL pyridine, mixed with 200 µL of a 40 mg/mL O -ethylhydroxylamine hydrochloride solution with 50 mM phenyl- β -D-glucopyranoside as internal standard and heated for 30 min at 70 °C on a rocking shaker.…”

Section: Methodsmentioning

confidence: 99%

Prebiotic Sugar Formation Under Nonaqueous Conditions and Mechanochemical Acceleration

Lamour

Pallmann

Haas

et al. 2019

Life

Self Cite

View full text Add to dashboard Cite

Monosaccharides represent one of the major building blocks of life. One of the plausible prebiotic synthesis routes is the formose network, which generates sugars from C1 and C2 carbon sources in basic aqueous solution. We report on the feasibility of the formation of monosaccharides under physical forces simulated in a ball mill starting from formaldehyde, glycolaldehyde, DL-glyceraldehyde as prebiotically available substrates using catalytically active, basic minerals. We investigated the influence of the mechanic energy input on our model system using calcium hydroxide in an oscillatory ball mill. We show that the synthesis of monosaccharides is kinetically accelerated under mechanochemical conditions. The resulting sugar mixture contains monosaccharides with straight and branched carbon chains as well as decomposition products. In comparison to the sugar formation in water, the monosaccharides formed under mechanochemical conditions are more stable and selectively synthesized. Our results imply the possibility of a prebiotic monosaccharide origin in geochemical environments scant or devoid of water promoted by mechanochemical forces such as meteorite impacts or lithospheric activity.

show abstract

Development of an advanced derivatization protocol for the unambiguous identification of monosaccharides in complex mixtures by gas and liquid chromatography

Cited by 37 publications

References 31 publications

Possible Ribose Synthesis in Carbonaceous Planetesimals

Possible Ribose Synthesis in Carbonaceous Planetesimals

Mineral-mediated carbohydrate synthesis by mechanical forces in a primordial geochemical setting

Prebiotic Sugar Formation Under Nonaqueous Conditions and Mechanochemical Acceleration

Contact Info

Product

Resources

About