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PubMed2025

Characterization of Micrococcus luteus Lipidome Containing Novel Lipid Families by Multiple Stage Linear Ion-Trap with High Resolution Mass Spectrometry.

Micrococcus luteus (M. luteus) is a ubiquitous, long-existing Gram-positive bacterium with a distinctive yellow or golden color. It is a model organism for laboratory studies due to its small genome and ease of cultivation. However, only limited knowledge about its constituent lipid structure is known, and its entire lipid profile remains unclear. Here, we applied linear ion trap (LIT) multiple-stage mass spectrometry (MSn) with high resolution for structural characterization of the native lipid extract, along with GC/MS analysis of the acid hydrolysate to reveal the structural details of the entire lipidome, which includes the major phosphatidylglycerol (PG), cardiolipin (CL), phosphatidylinositol (PI), dimannosyl diacylglycerol (DMDG), and minor diacylglycerol (DAG) lipid families. Importantly, we also found two extra lipid families, the new phosphatidyl 1,3-propanediol and the known polyprenyl 1-phosphosate that was not previously reported for M. luteus. We also revealed the unique lipidome simplified by the dominance of branched 15:0-fatty acid substituents (>90% branched 15:0-FA with anteiso-15:0 to iso-15:0 abundance ratio of 4/1), which is in line with the small genome of M. luteus. In addition, the applied LIT MSn mass spectrometry revealed a fragmentation pathway that undergoes internal loss of a glycerol residue specific to DMDG, leading to its structural characterization.

Micrococcus luteus↗
PubMed2001

Metabolism and distribution of [2,3-(14)C]acrolein in laying hens.

The metabolism and distribution of [2,3-(14)C]-acrolein were studied in 10 laying hens orally administered 1.09 mg/kg of body weight/day for 5 days. Eggs, excreta, and expired air were collected. The hens were killed 12-14 h after the last dose and edible tissues collected. The nature of radioactive residues was determined in tissues and eggs. All of the identified metabolites were the result of the incorporation of acrolein-derived radioactivity into normal natural products of intermediary metabolism in the hen except for 1,3-propanediol, which is a known degradation product of glycerol in bacteria.

Acrolein↗
PubMed2003

Purification and structural characterization of 3-hydroxypropionaldehyde and its derivatives.

The compound 3-hydroxypropionaldehyde (3-HPA), together with HPA hydrate and HPA dimer, in aqueous solution forms a system with interesting chemical properties. Therefore, 3-HPA has attracted attention by the chemical industry for use as a precursor in the production of plastics, acrylic acid, and 1,3-propanediol and by the food industry, in using 3-HPA-producing Lactobacillus reuteri as a probiotic. To produce 3-HPA in high yield from glycerol, L. reuteri was used as a biotransformation system. A convenient chromatographic purification method was developed, and purified 3-HPA was analyzed using electrospray ionization mass spectrometry and (13)C NMR. Quantitative (13)C NMR revealed a concentration-dependent distribution of the three compounds forming the HPA system. At concentrations above 1.4 M, the HPA dimer was predominant. However, at concentrations relevant for biological systems, HPA hydrate was the most abundant, followed by the aldehyde form. Our results indicate that the dimeric form with expected antibiotic properties should not be the active form.

Aldehydes↗
PubMed2003

Monitoring carbonyl-amine reaction between pyruvic acid and alpha-amino alcohols by FTIR spectroscopy--a possible route to Amadori products.

The carbonyl-amine reaction between pyruvic acid and alpha-amino alcohols was monitored by Fourier transform infrared spectroscopy at a temperature range between 20 and 100 degrees C and under acidic and basic conditions. To avoid interference, the reactions were conducted in the absence of solvent using liquid reactants such as methyl pyruvate, pyruvic acid, ethanolamine, and 1-amino-2,3-propanediol. Analysis of the time- and temperature-dependent spectra indicated that under basic conditions and at room temperature, the initial imine formation and its subsequent isomerization through a 1,3-prototropic shift occur very rapidly and the reaction goes to completion within 12 min. Interestingly, the isomerization product of the initial imine is the so-called Schiff base intermediate formed when the corresponding amino acid and the reducing sugar react during a typical Maillard reaction. Furthermore, the detailed studies also indicated that during the first 30 s, the rate of formation of the initial imine was faster than the rate of its isomerization; however, after 60 s, its rate of isomerization becomes faster than the rate of its formation. The data also indicated that under acidic conditions, this isomerization was prevented from occurring and the reaction was terminated at the initial imine formation stage. In addition, temperature-dependent spectra indicated that the isomerization of the Schiff's base into eneaminol can be achieved at or above 60 degrees C and its subsequent rearrangement into Amadori product can be attained at temperatures above 80 degrees C even under basic conditions, thus providing a novel route to Maillard reaction products starting from a keto acid and an amino alcohol. This observation was also confirmed through identification of the common Amadori product in both keto acid/amino alcohol and sugar/amino acid mixtures, by the application of tandem mass spectrometry and chemical ionization techniques.

Amino Alcohols↗
PubMed2004

Model studies on the formation of monochloropropanediols in the presence of lipase.

The formation of chloropropanols was investigated using model systems comprised of lipase, vegetable oil or fat, water, and sodium chloride. The results showed that measurable levels of the foodborne carcinogen 3-chloro-1,2-propanediol (3-MCPD) are formed in the presence of commercially available lipases of mammalian, vegetable, and fungal origins, incubated at temperatures of 40 degrees C. The highest yield of 3-MCPD was obtained in reaction mixtures containing lipase from Rhizopus oryzae, and all the lipases studied exhibited a high hydrolytic activity toward triglycerides from palm and peanut oil. In contrast, hydrolysis over time and the yield of 3-MCPD in olive and sunflower oils were significantly lower (up to 10-fold), possibly linked to the relatively lower amount (<18%) of saturated fatty acids in these oils. We provide here for the first time evidence that lipases are able to induce the formation of chloropropanols under model system conditions. However, the key intermediates and precise mechanistic aspects governing the formation of 3-MCPD in the presence of lipase still need to be elucidated.

Hydrogen-Ion Concentration↗
PubMed2000

Phase behavior and component partitioning in low water content amorphous carbohydrates and their potential impact on encapsulation of flavors.

The compositions at which amorphous ethanol-maltose-water mixtures exhibit liquid-liquid separation have been determined in the temperature range from 20 to 80 degrees C. At water contents below approximately 20% w/w two phases were observed, with the maltose-rich phase slightly richer in water. Partition coefficients of organic nonelectrolytes ranging in hydrophobicity from 1, 2-ethanediol and 1,2-propanediol to benzyl alcohol and propyl acetate have been measured for octanol/sorbitol, benzyl alcohol/sorbitol, and 1-butanol/sorbitol mixtures. Linear correlations were found between the log partition coefficients in the various solvent systems. Replacing water with sorbitol results in more organic partitioning into the octanol. Replacing octanol with benzyl alcohol or 1-butanol also results in more organic partitioning into the hydrophobic phase. The results establish a relationship with partition coefficients for octanol/water mixtures, which are well studied experimentally and for which predictive approaches exist. The implications of these results for flavor retention and encapsulation are discussed.

Carbohydrates↗
PubMed2000

Biodegradable films from isolate of sunflower (Helianthus annuus) proteins.

The film-forming potential of isolate of sunflower proteins (ISFP) was investigated. Homogeneous films were obtained by dissolution of ISFP in alkaline water (pH 12), addition of a plasticizer, casting, and drying. Maximum protein solubilization and unfolding led to films with the highest elasticity. The effects of five dissolving bases and five plasticizers on the mechanical properties were studied. The use of ionic bases (LiOH, NaOH) capable of interfering with the interproteic noncovalent bonds resulted in the greatest tensile strength (sigma(max)) and elongation at break (epsilon(max)) values (3.9 MPa and 215-251%, respectively). Plasticizers conferred diverse tensile properties to the films: the use of 1,3-propanediol resulted in the highest sigma(max) (27.1 MPa), and glycerol resulted in the greatest epsilon(max) (251%). Different mechanical properties were obtained by using mixtures of these plasticizers.

Biodegradation, Environmental↗
PubMed1995

Synthesis of cluster galactosides with high affinity for the hepatic asialoglycoprotein receptor.

High-affinity ligands for the asialoglycoprotein receptor, which is uniquely localized on the parenchymal liver cell and recognizes oligoantennary galactosides, might be utilized as homing device to specifically target drugs or genes to parenchymal liver cells. In the present study, the synthesis of galactose-terminated triantennary glycosides, provided with various spacers between the beta-galactopyranosyl moieties and the branching point of the dendrite, is described. N-[Tris[[(methylthio)methoxy]methyl]methyl]-N alpha-[1-(6- methyladipy)]glycinamide (3b) was glycosylated with monogalactosyl derivatives, containing propanediol or ethylene glycol units as hydrophilic spacer moieties, to yield the corresponding cluster galactosides. To determine the affinity of the cluster galactosides for the asialoglycoprotein receptor, we have performed competition studies of [125I]ASOR binding, a specific ligand for the asialoglycoprotein receptor, to isolated parenchymal cells. The affinity for the asialoglycoprotein receptor significantly increased with increasing spacer length. N-[[[Tris-O-(beta-D-galactopyranosyl)-3,6,9-trioxaunde- canoxy]methoxy]methyl]-N-alpha-[1-(6-methyladipyl)]glycinami de (4e), a cluster galactoside provided with a 20 A spacer, possessed an at least 2000-fold higher affinity for the receptor than N-[[tris-O-(beta-D-galactopyranosyl)methyl]methyl]-N alpha-[1-(6- methyladipyl)]glycinamide (4a), a cluster galactoside lacking the spacer. It is concluded that vicinal galactosyl moieties within a cluster galactoside are more optimal recognized by the galactose binding sites of the asialoglycoprotein receptor upon proper spacing. The most potent galactoside, TG(20A), may constitute an attractive targeting device for the specific delivery of drugs and/or genes to the parenchymal liver cell.

Animals↗
PubMed1995

Synthesis and antiviral activity of 8-aza analogs of chiral [2-(phosphonomethoxy) propyl]guanines.

(R)- And (S)-8-aza-9(-)[2-(phosphonomethoxy)propyl]guanine [(R)-and (S)-8-aza-PMPG] were synthesized and tested in vitro for anti-human immunodeficiency virus (HIV) activity. The synthesis of the above compounds and of (R)-9(-)[2-(phosphonomethoxy)propyl]guanine [(R)-PMPG] was carried out through the alkylation of 8-azaguanine or guanine with (R)- and (S)-2-O(-)[(diisopropylphosphono)methyl]-1-O-(tolylsulfonyl) -1,2-propanediol followed by deprotection of the phosphonic moiety. A different, even more convenient synthesis of (R)-8-aza-PMPG starting from 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone and (R)(-)[2(-)[(diisopropylphosphono)-methoxy]propyl]amine is also reported. Both (R)-8-aza-PMPG and (R)-PMPG demonstrated anti-HIV activity in the MTT assay with EC50 values of 12 and 4.5 microM, respectively. The corresponding S enantiomers were found to be less potent. When evaluated in combination with AZT, ddI, or DABO 603, (R)-8-aza-PMPG gave additive, additive, and synergistic anti-HIV-1 effects, respectively.

Antiviral Agents↗
PubMed1985

Synthesis and biological evaluation of 9-[5'-(2-oxo-1,3,2-oxazaphosphorinan-2-yl)-beta-D-arabinosyl]ade nine and 9-[5'-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-beta-D-arabinosyl]ade nine: potential neutral precursors of 9-[beta-D-arabinofuranosyl]adenine 5'-monophosphate.

9-[5'-(2-Oxo-1,3,2-oxazaphosphorinan-2-yl)-beta-D-arabinosyl]adeni ne (1c) and 9-[5'-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-beta-D-arabinosyl]adeni ne (1d) were synthesized by reaction of 9-[beta-D-arabinofuranosyl]adenine with phosphoryl chloride with 1-amino-3-propanol and 1,3-propanediol, respectively. 1c consisted of a mixture of diastereomers, while 1d was enantiomerically homogeneous. The structures of these compounds were established by spectral (1H NMR, MS, UV) and elemental analyses. Both 1c and 1d were resistant to degradation by 5'-nucleotidase, alkaline phosphatase, venom phosphodiesterase, crude snake venom, adenosine deaminase, and adenylate deaminase. Neither compound was significantly biotransformed by mouse hepatic microsomal preparations in the presence of an NADPH-generating system. Compound 1c was marginally effective at prolonging the life span of mice bearing P-388 leukemia; compound 1d, however, was inactive.

5'-Nucleotidase↗
PubMed1990

Synthesis and beta-adrenergic antagonist activity of stereoisomeric practolol and propranolol derivatives.

A series of stereoisomeric practolol and propranolol derivatives has been synthesized in which the N-isopropyl group of the drug was replaced by an asymmetric heptanoic acid terminated by a substituted p-toluidide or p-(trifluoromethyl)anilide. The asymmetric epoxide, 3-(p-acetamidophenoxy)-1,2-epoxypropane, was allowed to react with a preformed enantiomeric 6-aminoheptanoic acid amide to yield the stereoisomeric practolol congener derivatives. An asymmetric drug precursor epoxide was prepared from p-acetamidophenol and enantiomeric 3-(tosyloxy)-1,2-epoxypropane 6-aminoheptanoic acid amides were allowed to react with one of the enantiomers of 3-(1-naphthyloxy)-1,2-epoxypropane. This drug precursor epoxide was prepared either by combining 1-naphthol with enantiomeric 3-(tosyloxy)-1,2-epoxypropane (the Sharpless epoxide) or by combining 1-naphthol with enantiomeric 3-(tosyloxy)-1,2-propanediol followed by epoxidation. Pharmacological studies carried out for the practolol derivatives demonstrated a significant dependence of enhanced potency and tissue/subreceptor specificity on both the configuration of the drug asymmetric carbon and the configuration of the spacer asymmetric carbon. The compounds containing the S configuration at the drug asymmetric center and the R configuration at the spacer asymmetric carbon exhibited an increase in potency over the other stereoisomeric congener derivatives and the progenitor drug. For the propranolol congener derivatives, a large decrease in potency was observed for all of the stereoisomers over the progenitor drug. The propranolol stereoisomers containing the S configuration at the drug asymmetric center were more active than those containing the R configuration at that center.

Adipose Tissue↗
PubMed1977

3-Fluoro-1-hydroxypropan-2-one (fluorohydroxyacetone) and some esters. Syntheses and effects in BDF mice.

1-(Benzoyloxy), 1-(4-nitrobenzoyloxy), and 1-(3,5-dinitrobenzoyloxy) derivatives of 3-fluoro-, 3-chloro-, and 3-bromopropan-2-one were prepared by oxidation of the 1-benzoyloxy-3-halopropan-2-ols in turn prepared from the appropriate benzoyl chloride and 3-halo-1,2-propanediols, 1-Benzoyloxy-3-fluoropropan-2-one was allowed to react with acidic trimethyl orthoformate to yeild 1-benzoyloxy-2,2-dimethoxy-3-fluoropropane which upon basic hydrolysis afforded 2, 2-dimethoxy-3-fluoropropan-1-ol (fluorohydroxyacetone dimethyl ketal). This was deketalized with aqueous HCL to afford 3-fluoro-1-hydroxypropan-2-one (fluorohydroxyacetone), the title compound. By reacting 1-chloro-3-fluoropropan-2-one and 1, 3-dichloropropan-2-one with potassium acetate, 1-acetoxy-3-fluoropropan-2-one and 1-acetoxy-3-chloropropan-2-one (fluoro- and chlorohydroxyacetone acetate, respectively) were obtained. Similarly, sodium benzoate and 1-chloropropan-2-one produced 1-benzoyloxypropan-2-one. Stucture-activity relationships are discussed which relate chemical structure, alkylating ability, toxicity, and antitumor effects. Comparative toxicities in mice showed decreasing toxicity, on a molar basis, in the 1-benzoyloxy-3-halopropan-2-one series of bromo greater than fluoro greater than chloro. Ketones were much more toxic than the corresponding alcohols. In general the phosphate and benzoyloxy derivatives are more toxic than acetoxy compounds, with nitro-substituted benzoyloxy derivatives being much less toxic.

Acetone↗
PubMed1983

Synthesis and biological evaluation of neutral derivatives of 5-fluoro-2'-deoxyuridine 5'-phosphate.

5-Fluoro-5'-(2-oxo-1,3,2-oxazaphosphorinan-2-yl)-2'-deoxyuridine (1a) and 5-fluoro-5'-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-2'-deoxyuridine (1b) were prepared by reaction of 5-fluoro-2'-deoxyuridine (7a) and phosphoryl chloride with 3-amino-1-propanol and 1,3-propanediol, respectively. The thymidine analogues, 1c and 1d, were prepared similarly from thymidine. Compound 1b was synthesized in better yield from 13a and trimethylene phosphate with triphenylphosphine/diethyl azodicarboxylate as a condensing agent. Compounds 1a-d were resistant to degradation by 5'-nucleotidase, alkaline phosphatase, venom phosphodiesterase, and crude snake venom. None of these compounds were significantly biotransformed when incubated with mouse hepatic microsomal preparations in the presence of an NADPH-generating system. When administered intraperitoneally (ip) for 5 consecutive days, 1a was nearly as effective as 5-fluorouracil at prolonging the life spans of BDF1 mice implanted intraperitoneally with leukemia P-388. However, much larger dosages of 1a were required for optimal activity. Compound 1b administered similarly was only marginally effective. Neither 1a nor 1b was active against a P-388 mutant resistant to 5-fluorouracil.

5'-Nucleotidase↗
PubMed1988

Effects of sulfur-containing analogues of stearic acid on growth and fatty acid biosynthesis in the protozoan Crithidia fasciculata.

A variety of analogues of stearic acid in which one of the methylene groups was replaced by a sulfur atom were examined as inhibitors of growth and fatty acid biosynthesis in the trypanosomatid protozoan Crithidia fasciculata. The 8-, 9-, 10-, and 11-thiastearic acids were found to suppress the synthesis of the cyclopropane-containing fatty acid dihydrosterculic acid (9,10-methyleneoctadecanoic acid) at micromolar concentrations in the growth medium, and all but the 9-thiastearate were found to inhibit the growth of the protozoa at concentrations. The most potent inhibitor, 8-thiastearic acid (I50 for growth = 0.8 microM; I50 dihydrosterculate synthesis = 0.4 microM), was also observed to inhibit the synthesis of gamma-linolenic acid at a similar concentration. The sulfoxide derivatives of the 9- and 10-thiastearates were found to have little effect on growth or fatty acid synthesis, and several long-chain amides of 3-amino-1,2-propanediol were found to have effects similar to those of the fatty acids from which they were derived.

Animals↗
PubMed2002

Design, synthesis, and immunostimulatory properties of CpG DNAs containing alkyl-linker substitutions: role of nucleosides in the flanking sequences.

Bacterial and synthetic DNA containing unmethylated CpG dinucleotides activate the innate immune system and promote Th1-like immune responses. Recently, a receptor, TLR9, has been shown to recognize CpG DNA and activate immune cascade. But there have been no reports on the molecular mechanisms of recognition between CpG DNA and the receptor(s). Our earlier studies described a number of the chemical and structural characteristics of CpG dinucleotide and the sequences flanking the CpG dinucleotide that are critical for immunostimulatory activity. In the present study, we examined the effect of the presence and absence of a nucleoside in the flanking sequences by replacing one or two natural deoxyribonucleosides at various positions with one or more alkyl- (C2-C12), branched alkyl- (glyceryl or aminobutyryl-propanediol), or ethyleneglycol- (tri or hexa) linkers. The results suggest that a linker substitution at the first two nucleoside positions adjacent to the CpG dinucleotide on the 5'- or the 3'-side neutralizes the immunostimulatory activity, as determined by in vitro mouse spleen cell proliferation, cytokine secretion, and in vivo mouse spleen enlargement. The same substitutions placed about three to six nucleotides away from the CpG dinucleotide either did not affect or potentiated immunostimulatory activity compared with parent CpG-DNA without modifications. Substitution of deoxyribonucleosides with a C3 or C4 alkyl-linker was found to be optimal for potentiating immunostimulatory activity.

Adjuvants, Immunologic↗
PubMed2001

Synthesis of a fluorinated analogue of anticancer active ether lipids.

The synthesis of racemic 2'-(trimethylammonium)ethyl-3-hexadecyloxy-2-fluoro-2-(methoxymethyl)prop-1-yl-phosphate (6), a fluorinated analogue of an anticancer active ether lipid 5 was realized with 3% overall yield in a nine-step synthesis starting from 2-methylene-1,3-propanediol (7) using a bromofluorination as the key step. Both enantiomers of the precursor 8 of the ether lipid 6 were synthesized by lipase-catalyzed desymmetrization of the diacetate 17, either by hydrolysis (83% ee) or by lipase-catalyzed acetylation of the diol 22 (82% ee). The antitumor activity of 6 has been found in an in vivo model of the methylcholanthrene-induced fibrosarcoma of mice.

Animals↗
PubMed2003

Regulated-stereoselective construction of thirteen stereogenic centers necessary for the frame of (+)-discodermolide, based on iterative Lewis acid-promoted aldol reactions.

The segments C(1)-C(13) and C(15)-C(21) containing the 13 stereogenic centers required for the frame of (+)-discodermolide were synthesized in good to excellent enantio- and diastereoselectivities from a common racemic aldehyde, derived from 2-methyl-1,3-propanediol. The enantioselective aldol reactions of the racemic aldehyde with a silylketene acetal, derived from ethyl 2-bromopropionate, in the presence of chiral oxazaborolidinones, prepared in situ with N-p-toluenesulfonyl-(R)- and -(S)-valine and BH(3).THF, proceeded under kinetic control to give the stereotriads with a high degree of enantioselectivity. Enantioselective (chiral borane) and diastereoselective (BF(3).OEt(2) and TiCl(4)) aldol reactions with the silylketene acetal, coupled with diastereoselective radical debrominations (Bu(3)SnH, Et(3)B, with or without MgBr(2)), were used iteratively. This aldol reaction strategy for the construction of the polypropionate frame dramatically shortened the steps needed for the construction of the final segments.

Aldehydes↗
PubMed2004

Iron-catalyzed cross-coupling reactions. A scalable synthesis of the immunosuppressive agent FTY720.

A chemo- and regioselective cross-coupling reaction of the functionalized aryl triflate 5 with octylmagnesium bromide catalyzed by cheap, nontoxic, and environmentally benign Fe(acac)(3) sets the basis for a practical and scaleable synthesis of the octylbenzene derivative 6, which serves as a key building block for the preparation of FTY720 (1). This 2-amino-1,3-propanediol derivative shows highly promising immunosuppressive properties and is currently in human clinical phase III trials.

Catalysis↗