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All sourcesNASA NTRSDOE OSTI
NASA NTRS2016

Sugar and Sugar Derivatives in Residues Produced from the UV Irradiation of Astrophysical Ice Analogs

A large variety and number of organic compounds of prebiotic interest are known to be present in carbonaceous chondrites. Among them, one sugar (dihydroxyacetone) as well as several sugar acids, sugar alcohols, and other sugar derivatives have been reported in the Murchison and Murray meteorites. Their presence, along with amino acids, amphiphiles, and nucleobases strongly suggests that molecules essential to life can form abiotically under astrophysical conditions. This hypothesis is supported by laboratory studies on the formation of complex organic molecules from the ultraviolet (UV) irradiation of simulated astrophysical ice mixtures consisting of H2O, CO, CO2, CH3OH, CH4, NH3, etc., at low temperature. In the past 15 years, these studies have shown that the organic residues recovered at room temperature contain amino acids, amphiphiles, nucleobases, as well as other complex organics. However, no systematic search for the presence of sugars and sugar derivatives in laboratory residues have been reported to date, despite the fact that those compounds are of primary prebiotic significance. Indeed, only small (up to 3 carbon atoms) sugar derivatives including glycerol and glyceric acid have been detected in residues so far.

Ice Irradiation↗
NASA NTRS2017

Sugars and Sugar Derivatives in Residues Produced from the UV Irradiation of Astrophysical Ice Analogs

Carbonaceous chondrites contain a large variety of organic compounds of prebiotic interest, which include amino acids, amphiphiles, nucleobases, and sugar derivatives. The presence of these compounds strongly suggests that molecules essential to life can form abiotically under astrophysical conditions. Among the sugar derivatives reported in the Murchison and Murray meteorites, only one sugar (dihydroxyacetone) was found, together with a variety of sugar alcohols and sugar acids containing up to 6 carbon atoms, including sugar acid derivatives of the biological sugars ribose and glucose. On the other hand, laboratory studies on the formation of complex organic molecules from the ultraviolet (UV) irradiation of simulated astrophysical ice mixtures consisting of H2O, CO, CO2, CH3OH, CH4, NH3, etc., at low temperature have been routinely carried out in the past 15 years. These studies have shown that the organic residues recovered at room temperature contain amino acids, amphiphiles, nucleobases, as well as other complex organics, supporting a scenario in which molecules of prebiotic interest can form in extra-terrestrial environments.

Astrochemistry↗
NASA NTRS2017

Sugar Derivatives in Residues Produced from the UV Irradiation of Astrophysical Ice Analogs

A large variety of organic compounds of astrobiological and prebiotic interest have been detected in carbonaceous meteorites. These include amino acids, carboxylic acids, amphiphiles, functionalized nitrogen heterocycles such as nucleobases, functionalized polycylic aromatic hydrocarbons such as quinones, and sugar derivatives. The sugar derivatives identified in the Murchison and Murray meteorites are mainly sugar alcohols and sugar acids, and only the smallest sugar (dihydroxyacetone) has been detected. The presence of such a variety of organics in meteorites strongly suggests that molecules essential to life can form abiotically under astrophysical conditions. This hypothesis is further supported by laboratory studies in which astrophysical ice analogs (mixtures of H2O, CO, CO2, CH3OH, CH4, NH3, etc.) are subjected to ultraviolet (UV) irradiation at low temperature (<15 K) to simulate cold interstellar environments. These studies show that the organic residues recovered at room temperature after irradiation contain amino acids, amphiphiles, nucleobases, sugar derivatives, as well as other complex organic compounds. The finding of such compounds under plausible interstellar conditions is consistent with the presence of organic compounds in meteorites. Until very recently, no systematic search for the presence of sugar derivatives in laboratory residues had been carried out. The detection of ribose, the sugar constituent of RNA in all living systems, as well as other sugars, sugar alcohols, and sugar acids have been recently reported in one organic residue produced from the UV irradiation of an H2O:CH3OH:NH3 (10:3.5:1) ice mixture at 80 K. In this work, we present a detailed study of organic residues produced from the UV irradiation ice mixtures of several starting compositions (containing H2O, CH3OH, CO, CO2, and/or NH3) at <15 K for their sugar derivative content. Our results confirm the presence of all 3C‒5C sugar alcohols, several 3C‒5C sugars, and all 3C‒4C sugar acids (in decreasing order of abundances) in the residues. The higher abundances of sugar alcohols in these residues suggest a pathway in which sugar alcohols are formed first, while the formation of sugars and sugar acids require more steps. Finally, our results are compared with the detection of sugars derivatives in primitive meteorites.

Astrophysical Ice Analogs↗
NASA NTRS2018

Detailed Study of the Formation of Sugar Derivatives Produced from the UV Irradiation of Astrophysical Ice Analogs

Carbonaceous meteorites such as Murchison contain a large variety of organic compounds of astrobiological interest such as amino acids, other amphiphilic compounds, functionalized nitrogen heterocycles (including nucleobases), functionalized polycylic aromatic hydro-carbons (including quinones), and sugar derivatives. The presence of such a broad variety of organics in meteorites strongly suggests that molecules essential to life can form abiotically under astrophysical conditions. This hypothesis is strongly supported by laboratory studies in which astrophysical ice analogs (i.e., mixtures of H2O, CO, CO2, CH3OH, CH4, NH3, etc.) are subjected to ultraviolet (UV) irradiation at low temperature (less than 15 K) to simulate cold interstellar environments. These studies have shown that the organic residues recovered at room temperature after irradiation contain organic compounds that are very similar to those found in meteorites. No systematic search for the presence of sugar derivatives in laboratory residues had been carried out until the recent detection of ribose, the sugar of RNA, as well as other sugars, sugar alcohols, and sugar acids in one residue produced from the UV irradiation of an ice mixture containing H2O, CH3OH, and NH3 at 80 K. In this work, we present a detailed study of the formation of sugar derivatives contained in organic residues that are produced from the UV irradiation of ice mixtures of different starting compositions (H2O, CH3OH, CO, CO2, and/or NH3) at less than 15 K. While the presence of sugar alcohols, sugars, and sugar acids-in some cases with up to 6 carbon atoms-could be confirmed in all these residues, their distribution was shown to vary with the composition of the starting ices. In particular, only a few ices result in the formation of sugar derivatives displaying a distribution that resembles that of meteorites, in which sugar alcohols and sugar acids are very abundant while sugars are mostly absent.

Photochemistry↗
NASA NTRS2015

Search for Sugars and Related Compounds in Residues Produced from the UV Irradiation of Astrophysical Ice Analogs

A large variety and number of organic compounds of prebiotic interest have been detected in meteorites. Among them, one sugar (dihydroxyacetone) as well as several sugar acids and sugar alcohols have been detected in Murchison and Murray [1]. Their presence in meteorites, along with amino acids, amphiphiles, and nucleobases [2-6], strongly suggests that molecules essential to life can form abiotically under astrophysical conditions. This hypothesis is supported by laboratory studies on the formation of complex organic molecules from the ultraviolet (UV) irradiation of astrophysical ice analogs (H2O, CO, CO2, CH3OH, CH4, NH3, etc.). These studies show that the organic residues recovered at room temperature after the UV irradiation of such ice mixtures contain amino acids [7-9], amphiphiles [4], nucleobases [10-13], and other organic complex organic compounds [14-16]. However, no systematic search for the presence of sugars, sugar acids, and sugar alcohols in laboratory residues have been reported to date, despite the fact that those compounds are involved in a large number of biological processes. Only a limited number of small (less than or equal to 3 carbon atoms) sugar derivatives such as glycerol and glyceric acid have been detected in residues [14-16]. In this work, we show results obtained from the systematic search for sugars and sugar-related compounds in organic residues produced from the UV irradiation of simple CH3OH and H2O+CH3OH ices, and more astrophysically relevant ice mixtures containing H2O, CH3OH, CO, and NH3. The results are compared with measurements of sugars and related compounds in primitive meteorites.

Murchison and Murray↗
NASA NTRS2002

Enantiomeric and Isotopic Analysis of Sugar Derivatives in Carbonaceous Meteorites

Several classes of organic compounds are found in carbonaceous meteorites including amino acids, carboxylic acids, hydroxy acids, purines, and pyrimidines. Such compounds are thought to have been delivered to the early Earth in asteroids and comets and may have played a role in the origin of life. Likewise, sugar derivatives are critical to all known lifeforms. Recent analyses of the Murchison and Murray carbonaceous meteorites revealed a diverse suite of such derivatives, i.e., sugar alcohols, and sugar acids. This presentation will focus primarily on the analysis of individual sugar acids - their enantiomeric and isotopic composition. Analysis of these compounds may reveal the nature of past (or present) meteoritic sugars themselves. For example, if parent sugars decomposed (by well-known mechanisms) to give the present acids, were their enantiomeric ratios preserved? Combined with other evidence, the enantiomeric composition of such compounds as glyceric acid and (especially) rare acids may help to answer such questions. C-13 and D isotope analysis of meteoritic sugar alcohols (glycerol, threitol, ribitol, etc.) as a group revealed that they were indigenous to the meteorite. Preliminary C-13 analysis of glyceric acid shows that it is also extraterrestrial.

Cooper, George↗
NASA NTRS2012

Enantiomer Ratios of Meteoritic Sugar Derivatives

Carbonaceous meteorites contain a diverse suite of soluble organic compounds. Studies of these compounds reveal the Solar System's earliest organic chemistry. Among the classes of organic compounds found in meteorites are keto acids (pyruvic acid, etc.), hydroxy tricarboxylic acids (1), amino acids, amides, purines and pyrimidines. The Murchison and Murray meteorites are the most studied for soluble and insoluble organic compounds and organic carbon phases. The majority of (indigenous) meteoritic compounds are racemic, (i.e., their D/L enantiomer ratios are 50:50). However, some of the more unusual (non-protein) amino acids contain slightly more of one enantiomer (usually the L) than the other. This presentation focuses on the enantiomer analyses of three to six-carbon (3C to 6C) meteoritic sugar acids. The molecular and enantiomer analysis of corresponding sugar alcohols will also be discussed. Detailed analytical procedures for sugar-acid enantiomers have been described. Results of several meteorite analyses show that glyceric acid is consistently racemic (or nearly so) as expected of non-biological mechanisms of synthesis. Also racemic are 4-C deoxy sugar acids: 2-methyl glyceric acid; 2,4-dihydroxybutyric acid; 2,3-dihydroxybutyric acid (two diastereomers); and 3,4-dihydroxybutyric acid. However, a 4C acid, threonic acid, has never been observed as racemic, i.e., it possesses a large D excess. In several samples of Murchison and one of GRA 95229 (possibly the most pristine carbonaceous meteorite yet analyzed) threonic acid has nearly the same D enrichment. In Murchison, preliminary isotopic measurements of individual threonic acid enantiomers point towards extraterrestrial sources of the D enrichment. Enantiomer analyses of the 5C mono-sugar acids, ribonic, arabinonic, xylonic, and lyxonic also show large D excesses. It is worth noting that all four of these acids (all of the possible straight-chained 5C sugar acids) are present in meteorites, including the rare lyxonic acid, and their relative abundances are in equilibrium proportions. In addition (in contrast to the above D-only excesses), some of the above acids are found in biology as the L enantiomer. Whether rare are common, all of the 6C sugar acids that are present in sufficient amounts to allow enantiomer analysis (Mannonic, gluconic, altronic, talonic, idonic, gulonic, and galactonic) also, apparently, possess significant D excesses.

Cooper, George↗
NASA NTRS2003

Prebiotic Synthesis of Autocatalytic Products From Formaldehyde-Derived Sugars as the Carbon and Energy Source

Our research objective is to understand and model the chemical processes on the primitive Earth that generated the first autocatalytic molecules and microstructures involved in the origin of life. Our approach involves: (a) investigation of a model origin-of-life process named the Sugar Model that is based on the reaction of formaldehyde- derived sugars (trioses and tetroses) with ammonia, and (b) elucidation of the constraints imposed on the chemistry of the origin of life by the fixed energies and rates of C,H,O-organic reactions under mild aqueous conditions. Recently, we demonstrated that under mild aqueous conditions the Sugar Model process yields autocatalytic products, and generates organic micropherules (2-20 micron dia.) that exhibit budding, size uniformity, and chain formation. We also discovered that the sugar substrates of the Sugar Model are capable of reducing nitrite to ammonia under mild aqueous conditions. In addition studies done in collaboration with Sandra Pizzarrello (Arizona State University) revealed that chiral amino acids (including meteoritic isovaline) catalyze both the synthesis and specific handedness of chiral sugars. Our systematic survey of the energies and rates of reactions of C,H,O-organic substrates under mild aqueous conditions revealed several general principles (rules) that govern the direction and rate of organic reactions. These reactivity principles constrain the structure of chemical pathways used in the origin of life, and in modern and primitive metabolism.

Weber, Arthur L.↗
NASA NTRS2015

Search for Sugars and Related Compounds in Residues Produced from the UV Irradiation of Astrophysical Ice Analogs

A large variety of organics of biological and prebiotic interests have been detected in meteorites, including one sugar and several sugar acids and sugar alcohols [1]. The presence of these compounds in meteorites, along with amino acids, amphiphiles, and nucleobases [2-4], indicates that molecules essential to life can be formed abiotically under astrophysical conditions. This hypothesis is supported by extensive laboratory studies involving the formation of complex organic molecules from the ultraviolet (UV) irradiation of astrophysical ice analogs (H2O, CO, CO2, CH3OH, CH4, NH3, etc.). These studies show that the organic residues recovered at room temperature contain many of the same compounds as those found in meteorites[3,58]. However, to the best of our knowledge, no systematic search for the presence of sugars and sugar derivatives in such laboratory residues have been reported to date. Only a limited number of small (greater than 4 C atoms) sugar-related compounds such as glycerol and glyceric acid [9], and more recently small (2-4 C atoms) aldehydes [10] have been detected in residues.

Astrophysics↗
NASA NTRS2006

Bacterial Utilization of L-sugars and D-amino Acids

The fact that organotrophic organisms on Earth use L-amino acids and D-sugars as an energy source is recognized as one of the universal features of life. The chirality of organic molecules with asymmetric location of group- radicals was described a relatively long time ago. In 1848, Louis Pasteur discovered chiral molecules when he investigated the way that crystals of sodium ammonium paratartrate rotated the plane of polarization of light. He found that the crystal structures represented the underlying asymmetry of molecules that existed in either lea-handed or right-handed forms (enantiomers). Pasteur observed that abiotic (chemical) processes produced mixtures with equal numbers (racemic) of the two forms but that living organisms possessed a molecular asymmetry that included only one of the enantiomers (homochirality). He speculated that the origin of the asymmetry of chiral biomolecules might hold the key to the nature of life. All of the amino acids in proteins (except for Glycine which is symmetrical) exhibit the same absolute steric configuration as L-glyceraldehyde. D-amino acids are never found in proteins, although they do exist in nature and are often found in polypeptide antibiotics. Constitutional sugars of cells, opposite to the amino acids, are the D-enantiomers, and the appearance of L-sugars in Nature is extremely rare. Notwithstanding this fact, the metabolism of some bacteria does have capability to use amino acids and sugars with alternative chirality. This property may be caused by the function of specific enzymes belonging to the class of isomerases (racemases, epimerases, isomerases, tautomerases). In our laboratory, we have investigated several anaerobic bacterial strains, and have found that some of these bacteria are capable of using D-amino acids and L-sugars. Strain BK1 is capable of growth on D-arginine, but its growth characteristics on L-arginine are approximately twice higher. Another alkaliphilic strain SCAT(sup T) (= ATCC BAA-1084(sup T)= JCM 12857(sup T) = DSM 17722(sup T) = CIP 107910(sup T)) was found to be capable of growth on L-ribose and L-arabinose. It is interesting that this strain was incapable of growth on D-arabinose, which suggests the involvement of some alternative mechanism of enzyme activity. In this paper, we describe the preliminary results of these microbiological studies and discuss some possible implications.

Pikuta, Elena↗
NASA NTRS2001

The sugar model: catalysis by amines and amino acid products

Ammonia and amines (including amino acids) were shown to catalyze the formation of sugars from formaldehyde and glycolaldehyde, and the subsequent conversion of sugars to carbonylcontaining products under the conditions studied (pH 5.5 and 50 degrees C). Sterically unhindered primary amines were better catalysts than ammonia, secondary amines, and sterically hindered primary amines (i.e. alpha-aminoisobutyric acid). Reactions catalyzed by primary amines initially consumed formaldehyde and glycolaldehyde about 15-20 times faster than an uncatalyzed control reaction. The amine-catalyzed reactions yielded aldotriose (glyceraldehyde), ketotriose (dihydroxyacetone), aldotetroses (erythrose and threose), ketotetrose (erythrulose), pyruvaldehyde, acetaldehyde, glyoxal, pyruvate, glyoxylate, and several unindentified carbonyl products. The concentrations of the carbonyl products, except pyruvate and ketotetrose, initially increased and then declined during the reaction, indicating their ultimate conversion to other products (like larger sugars or pyruvate). The uncatalyzed control reaction yielded no pyruvate or glyoxylate, and only trace amounts of pyruvaldehyde, acetaldehyde and glyoxal. In the presence of 15 mM catalytic primary amine, such as alanine, the rates of triose and pyruvaldehyde of synthesis were about 15-times and 1200-times faster, respectively, than the uncatalyzed reaction. Since previous studies established that alanine is synthesized from glycolaldehyde and formaldehyde via pyruvaldehyde as its direct precursor, the demonstration that the alanine catalyzes the conversion of glycolaldehyde and formaldehyde to pyruvaldehyde indicates that this synthetic pathway is capable of autocatalysis. The relevance of this synthetic process, named the Sugar Model, to the origin of life is discussed.

Acetaldehyde/analogs & derivatives/chemistry↗
NASA NTRS1990

The conversion of lignocellulosics to fermentable sugars - A survey of current research and applications to CELSS

This report provides an overview options for converting lignocellulosics into fermentable sugars in CELSS. A requirement for pretreatment is shown. Physical-chemical and enzymatic hydrolysis processes for producing fermentable sugars are discussed. At present physical-chemical methods are the simplest and best characterized options, but enzymatic processes will be the likely method of choice in the future. The use of pentose sugars by microorganisms to produce edibles is possible. The use of mycelial food production on pretreated but not hydrolyzed lignocellulosics is also possible. Simple trade-off analyses to regenerate waste lignocellulosics for two pathways are made, one of which is compared to complete oxidation.

Petersen, Gene R.↗
NASA NTRS1995

Rates of Decomposition of Ribose and other Sugars: Implications for Chemical Evolution

The existence of the RNA world, in which RNA acted as a catalyst as well as an informational macromolecule, assumes a large prebiotic source of ribose or the existence of pre-RNA molecules with backbones different from ribose-phosphate. The generally accepted prebiotic synthesis of ribose, the formose reaction, yields numerous sugars without any selectivity. Even if there were a selective synthesis of ribose, there is still the problem of stability. Sugars are known to be unstable in strong acid or base, but there are few data for neutral solutions. Therefore, we have measured the rate of decomposition of ribose between pH 4 and pH 8 from 40 C to 120 C. The ribose half-lives are very short (73 min at pH 7.0 and 100 C and 44 years at pH 7.0 and 0 C). The other aldopentoses and aldohexoses have half-lives within an order of magnitude of these values, as do 2-deoxyribose, ribose 5-phosphate, and ribose 2,4bisphosphate. These results suggest that the backbone of the first genetic material could not have contained ribose or other sugars because of their instability.

Larralde, Rosa↗
NASA NTRS1996

The Metabolic World: Sugars as an Energized Carbon Substrate for Prebiotic and Biotic Synthesis

To understand the origin of metabolism and biopolymer synthesis we investigated the energy sources that drive anabolic metabolism. We found that biosynthesis of amino acids and lipids from sugars is driven bz the free energy of redox disproportionation of carbon (see discussion or next page). The indispensable role of sugar disproportionation in the biosynthesis of amino acids and lipids suggests that the origin of life uses the same chemical engine, and was therefore based on nonenzymatic redox disproportionation reactions of sugars that occurred in the presence o ammonia and hydrogen sulfide. The chemistry of this 'metabolic' model of the origin of life is described.

Weber, Arthur L.↗
NASA NTRS2001

Carbonaceous meteorites as a source of sugar-related organic compounds for the early Earth

The much-studied Murchison meteorite is generally used as the standard reference for organic compounds in extraterrestrial material. Amino acids and other organic compounds important in contemporary biochemistry are thought to have been delivered to the early Earth by asteroids and comets, where they may have played a role in the origin of life. Polyhydroxylated compounds (polyols) such as sugars, sugar alcohols and sugar acids are vital to all known lifeforms-they are components of nucleic acids (RNA, DNA), cell membranes and also act as energy sources. But there has hitherto been no conclusive evidence for the existence of polyols in meteorites, leaving a gap in our understanding of the origins of biologically important organic compounds on Earth. Here we report that a variety of polyols are present in, and indigenous to, the Murchison and Murray meteorites in amounts comparable to amino acids. Analyses of water extracts indicate that extraterrestrial processes including photolysis and formaldehyde chemistry could account for the observed compounds. We conclude from this that polyols were present on the early Earth and therefore at least available for incorporation into the first forms of life.

Biogenesis↗
NASA NTRS2005

Electron-impact total ionization cross sections of DNA sugar-phosphate backbone and an additivity principle

The improved binary-encounter dipole (iBED) model [W.M. Huo, Phys. Rev. A64, 042719-1 (2001)l is used to study the total ionization cross sections of the DNA sugar-phosphate backbone by electron impact. Calculations using neutral fragments found that the total ionization cross sections of C3' - and C5', -deoxyribose-phospate, two conformers of the sugar-phosphate backbone, are close to each other. Furthermore, the sum of the ionization cross sections of the separate deoxyribose and phosphate fragments is in close agreement with the C3' - and C5" -deoxyribose-phospate cross sections, differing by less than 10%. The result implies that certain properties of the-DNA, like the total singly ionization cross section, are localized properties and a building-up or additivity principle may apply. This allows us to obtain accurate properties of larger molecular systems built up from the results of smaller subsystem fragments. Calculations are underway using a negatively charged sugar-phosphate backbone with a metal counter-ion.

Huo, Winifred M.↗
NASA NTRS1981

The changes in leaf reflectance of sugar maple seedlings (Acer saccharum Marsh) in response to heavy metal stress

The effects of heavy metal stress on leaf reflectance of sugar maple seedlings (Acer saccharum Marsh) are examined. It is found that sugar maple seedlings treated with anomalous amounts of heavy metals in the rooting medium exhibited an increased leaf reflectance over the entire range of investigated wavelengths, from 475 to 1650 nm. These results conform to those of a previous investigation in the wavelengths from 475 to 660nm, but tend to contradict the previous study in the near infrared wavelengths from 1000 to 1650nm. The differences may possible be due to different water regimes in the two investigations.

Schwaller, M. R.↗
NASA NTRS1983

The changes in leaf reflectance of sugar maple (Acer saccharum Marsh) seedlings in response to heavy metal stress

The effects of heavy metal stress on leaf reflectance of sugar maple seedlings (Acer saccharum Marsh) are examined. It is found that sugar maple seedlings treated with anomalous amounts of heavy metals in the rooting medium exhibited an increased leaf reflectance over the entire range of investigated wavelengths, from 475 to 1650 nm. These results conform to those of a previous investigation in the wavelengths from 475 to 660 nm, but tend to contradict the previous study in the near infrared wavelengths from 1000 to 1650 nm. The differences may possibly be due to different water regimes in the two investigations. Previously announced in STAR as N81-29729

Schwaller, M. R.↗