The Gram-negative gliding bacteria Lysobacter represent a new and rich source for bioactive natur... more The Gram-negative gliding bacteria Lysobacter represent a new and rich source for bioactive natural products. In an effort to discover new antibiotics, we found a cryptic biosynthetic gene cluster (BGC) in Lysobacter sp. 3655 that shared a high similarity with the putative lysocin BGC identified in silico previously from Lysobacter sp. RH2180-5. Lysocins are cyclic lipodepsipeptides with potent activity against MRSA (methicillin-resistant Staphylococcus aureus) using a novel mode of action, but the lysocin BGC had not been experimentally verified so far. Using an activity-guided screening, we isolated the main antibiotic compound and confirmed it to be lysocin E. However, the putative lysocin BGC was barely transcribed in the wild type, in which lysocins were produced only in specific conditions and in a negligible amount. To activate the putative lysocin BGC, we screened for strongly transcribed housekeeping genes in strain 3655 and found several powerful promoters. Upon engineering the promoters into the BGC, the lysocin gene transcription was significantly enhanced and the lysocin yield was markedly increased. With readily detectable lysocins production in the engineered strains, we showed that lysocin production was abolished in the gene deletion mutant and then restored in the complementary strain, even when grown in conditions that did not support the wild type for lysocin production. Moreover, the engineered strain produced multiple new lysocin congeners. The determination of the lysocin BGC and the Lysobacter promoters will facilitate the ongoing efforts for yield improvement and new antibiotics biosynthesis using synthetic biology strategies.
Journal of Agricultural and Food Chemistry, Apr 1, 1997
The detection of the sulfonic acid metabolites of the chloroacetanilide herbicides acetochlor, al... more The detection of the sulfonic acid metabolites of the chloroacetanilide herbicides acetochlor, alachlor, butachlor, propachlor, and, more recently, metolachlor in surface and ground water suggests that a common mechanism for dechlorination exists via the glutathione conjugation pathway. The identification of these herbicides and their metabolites is important due to growing public awareness and concern about pesticide levels in drinking water. Although these herbicides are regulated, little is known about the fate of their metabolites in soil. The sulfonic acid metabolites were synthesized by reaction of the parent compounds with an excess of sodium sulfite. Acetochlor, alachlor, butachlor, metolachlor, and propachlor and their sulfonic acid metabolites were studied by nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. This paper provides a direct method for the preparation and characterization of these compounds that will be useful in the analysis and study of chloracetanilide herbicides and their metabolites.
Protein biochemistry protocols typically include disulfide bond reducing agents to guard against ... more Protein biochemistry protocols typically include disulfide bond reducing agents to guard against unwanted thiol oxidation and protein aggregation. Commonly used disulfide bond reducing agents include dithiothreitol, β-mercaptoethanol, glutathione, and the tris(alkyl)phosphine compounds tris(2-carboxyethyl)phosphine (TCEP) and tris(3-hydroxypropyl)phosphine (THPP). While studying the catalytic activity of the NAD(P)H-dependent enzyme Δ1-pyrroline-5-carboxylate reductase, we unexpectedly observed a rapid non-enzymatic chemical reaction between NAD+ and the reducing agents TCEP and THPP. The product of the reaction exhibits a maximum ultraviolet absorbance peak at 334 nm and forms with an apparent association rate constant of 231–491 M−1 s−1. The reaction is reversible, and nuclear magnetic resonance characterization (1H, 13C, and 31P) of the product revealed a covalent adduct between the phosphorus of the tris(alkyl)phosphine reducing agent and the C4 atom of the nicotinamide ring of NAD+. We also report a 1.45 Å resolution crystal structure of short-chain dehydrogenase/reductase with the NADP+–TCEP reaction product bound in the cofactor binding site, which shows that the adduct can potentially inhibit enzymes. These findings serve to caution researchers when using TCEP or THPP in experimental protocols with NAD(P)+. Because NAD(P)+-dependent oxidoreductases are widespread in nature, our results may be broadly relevant.
ABSTRACT The photophysical properties of a metal chelating pyridyl-based aromatic ureas and poly(... more ABSTRACT The photophysical properties of a metal chelating pyridyl-based aromatic ureas and poly(1,4-phenylene-2,6-pyridylurea) were investigated. In their solution state and upon exposure to 365 nm UV radiation, these low and high molecular weight compounds were found to cleave the urea linkage nearly quantitatively, generating the corresponding amine-terminated subunits and CO2. Through a series of model compounds along with nuclear magnetic resonance (NMR), UV/vis absorption, and fluorescence spectroscopy characterization, the photocleavage process was delineated as a function of UV dose, O2, and water. The presence of water was found crucial to this photocleavage process with O2 playing a role only in subsequent oxidation of resulting amine functionalities. The experimental results support a light-assisted hydrolysis of the urea bond as the most plausible photocleavage mechanism. The photocleavage of such pyridyl-based ureas can potentially find usages in light-assisted base generation and/or for releasing metal cations.
To determine changes in the grain components between historical and modern wheat (Triticum aestiv... more To determine changes in the grain components between historical and modern wheat (Triticum aestivum L.) cultivars, wholemeal flours from 19 wheat cultivars and 2 landraces released or introduced between 1870 and 2013 and grown over two crop years were extracted using hydroalcoholic solution and analyzed using one dimensional 1 H NMR spectral profiling. Grain yield, grain volume weight (GVW), and grain protein concentration were also measured. Grain yield increased while protein concentration decreased by release year (p < 0.001). Increasing trends (p < 0.01) were observed for tryptophan, sum of the measured amino acids, chlorogenic acid, ferulic acid, vanillic acid, and sum of the measured phenolic acids. Grain yield, phenolic acids, and tryptophan were mainly associated with modern cultivars, whereas grain protein concentration and GVW were associated with historical cultivars. The findings from this study showed changes in concentration of grain components over a century of breeding that may have implications for grain quality and human health.
This study used multiple chemical-rheological tests to investigate the long-term characteristics ... more This study used multiple chemical-rheological tests to investigate the long-term characteristics of rejuvenating agents in reclaimed asphalt binders. To this end, a base binder and its blending with an extracted binder obtained from recycled asphalt pavements were selected, and two different types of rejuvenating agents: agriculture-based and petroleum-based agents were used to modify the blended binder. The base binder and the blended binders that were modified by the two rejuvenators were then aged using a typical laboratory long-term aging procedure. The chemical studies included: a saturates-aromatics-resins-asphaltenes analysis, Fourier transform infrared spectroscopy, and elemental (carbon, hydrogen, nitrogen, sulfur and oxygen) analysis. The rheological tests primarily investigated the linear viscoelastic properties through aging and rejuvenation. The effects of rejuvenators on restoration were quite material-dependent, which was related to the different chemical compositions of the rejuvenators and their chemical-molecular interactions with the parent binder. The tests and analysis results showed that the immediate effects of rejuvenators are mostly the result of the addition of lighter molecules in rejuvenators, while the long-term effects were material-specific and further chemistry-driven. From the two rejuvenating agents studied herein, the petroleum-based material improves performance of the binder in the next round of service by preserving the chemical composition and maintaining the
ABSTRACT We have prepared a series of indocyanine green dicarboxylic acid derivatives (9a,b, 4, 1... more ABSTRACT We have prepared a series of indocyanine green dicarboxylic acid derivatives (9a,b, 4, 10, 13) with modified polyene linkers in an attempt to increase the structural rigidity of the polyene linker and thereby the fluorescent yield. Incorporation of five- and six-membered rings into the polyene system led to lower florescent yield for 9a,b, 4 and 10, but shortening the chain by two carbon atoms led to an increase in fluorescent yield for 13.
Chemical shifts are reported in units of parts per million (ppm). IR spectra were recorded on an ... more Chemical shifts are reported in units of parts per million (ppm). IR spectra were recorded on an FT-IR spectrometer. GC/MS spectra were obtained on a gas chromatograph equipped with a HP-1 methyl silicon column and detected on a low-resolution 5970 series mass selective detector. High resolution mass spectra were obtained on a micrOTOF instrument. Column chromatography was performed using silica gel, 40 microns flash silica. Thin layer chromatography was performed on silica gel (Silica Gel 60 F 254) glass plates, and the compounds were visualized by UV and 5% solution of phosphomolybdic acid in 95% EtOH.
Porphyromonas gingivalis , a recognized periodontal pathogen, synthesizes free ceramides as well ... more Porphyromonas gingivalis , a recognized periodontal pathogen, synthesizes free ceramides as well as other phosphorylated ceramide lipids. The purpose of this study was to separate complex lipids of P. gingivalis by high-performance liquid chromatography (HPLC) and determine the structures and biological activities of the major ceramide classes. Using gas chromatography-mass spectrometry, electrospray tandem mass spectrometry (ESI-MS/MS) and NMR analyses, three major classes of dihydroceramides were identified in specific HPLC fractions, with all classes containing the same dihydroceramide base structures (3-OH iso C 17:0 in amide linkage to saturated long-chain bases of 17, 18, or 19 carbons). The free dihydroceramide class recovered in HPLC fractions 7-8 revealed little biological activity. HPLC fraction 20 dihydroceramides, substituted with 1-O-phosphoglycerol and iso C 15:0 linked to the hydroxyl of 3-OH iso C 17:0 , significantly potentiated interleukin-1  (IL-1 )-mediated prostaglandin secretion and produced marked alterations in fibroblast morphology. HPLC fraction 28 dihydroceramides, substituted with 1-O-phosphoethanolamine, demonstrated little capacity to potentiate IL-1 -mediated prostaglandin secretion. The novel phosphorylated dihydroceramides synthesized by P. gingivalis demonstrate varying biological activities based on the phosphorylated head group substitution and/or the addition of esterified fatty acid. These results also demonstrate the strong virulence capacity of phosphoglycerol dihydroceramides of P. gingivalis to promote inflammatory factor secretion from IL-1 -treated fibroblasts and to produce marked alterations in cell morphology in culture.-Nichols, F. C., B.
In the present contribution, the intrinsic dynamics of the Alq3 molecule has been studied using t... more In the present contribution, the intrinsic dynamics of the Alq3 molecule has been studied using two dimensional exchange NMR spectroscopy. The understanding of the intrinsic internal dynamics of the Alq3 complex provides the basis for future studies of dynamic processes. This information will contribute towards understanding both the processing and degradation of Alq3 based organic LED devices.
The inhibition of sialyl Lewis X can prevent unwanted cellular extravasation that is associated w... more The inhibition of sialyl Lewis X can prevent unwanted cellular extravasation that is associated with inflammatory diseases and tumor metastasis. Described is an efficient methodology to prepare peracetylated GlcNAcβ3Gal-aglycone disaccharides subsequently used as metabolic decoys to inhibit sialyl Lewis X expression. Four glycosides were synthesized from one single parent disaccharide that in turn was prepared by large-scale enzymatic synthesis. The
Journal of Pharmaceutical and Biomedical Analysis, Sep 1, 1995
19F NMR spectroscopy of a model fluoroquinolone, lomefloxacin, in an erythrocyte suspension showe... more 19F NMR spectroscopy of a model fluoroquinolone, lomefloxacin, in an erythrocyte suspension showed separate resonances for the intra- and extra-cellular compartments. The intra-cellular peak revealed significant line broadening of the fluorine signals of lomefloxacin. Line broadening also occurred in the presence of oxyhemoglobin (HbO2), hematin, globin and iron. This evidence indicated that lomefloxacin interacted with these compounds; however, ultrafiltration experiments indicated that there was only weak binding (5%) of lomefloxacin to HbO2. 19F and 31P NMR spectroscopy revealed that lomefloxacin may compete with 2,3-diphosphoglycerate for its binding site on HbO2. An apparent partition coefficient of 1.90 +/- 0.15 was observed for lomefloxacin in human erythrocytes, utilizing LC analysis.
The polymer PEDOT + (1 or 2) mediates a cyclodehydration reaction with alditols 3, 5, 7, 9, in hy... more The polymer PEDOT + (1 or 2) mediates a cyclodehydration reaction with alditols 3, 5, 7, 9, in hydrocarbon solvents, to give cyclic ethers 4, 6, 8, or 10, respectively, in high yield with a trivial isolation protocol. Polymers 1 or 2 also mediate the cyclodehydration of ketohexoses such as D-fructose, but not aldohexoses, to the important industrial intermediate 5-hydroxymethylfurfural (17), under milder conditions when compared to reactions mediated by mineral acids. A cascade reaction with ketohexoses is observed in toluene via cyclodehydration followed by Friedel-Crafts alkylation of the initially formed benzylic alcohol to give 16.
The Gram-negative gliding bacteria Lysobacter represent a new and rich source for bioactive natur... more The Gram-negative gliding bacteria Lysobacter represent a new and rich source for bioactive natural products. In an effort to discover new antibiotics, we found a cryptic biosynthetic gene cluster (BGC) in Lysobacter sp. 3655 that shared a high similarity with the putative lysocin BGC identified in silico previously from Lysobacter sp. RH2180-5. Lysocins are cyclic lipodepsipeptides with potent activity against MRSA (methicillin-resistant Staphylococcus aureus) using a novel mode of action, but the lysocin BGC had not been experimentally verified so far. Using an activity-guided screening, we isolated the main antibiotic compound and confirmed it to be lysocin E. However, the putative lysocin BGC was barely transcribed in the wild type, in which lysocins were produced only in specific conditions and in a negligible amount. To activate the putative lysocin BGC, we screened for strongly transcribed housekeeping genes in strain 3655 and found several powerful promoters. Upon engineering the promoters into the BGC, the lysocin gene transcription was significantly enhanced and the lysocin yield was markedly increased. With readily detectable lysocins production in the engineered strains, we showed that lysocin production was abolished in the gene deletion mutant and then restored in the complementary strain, even when grown in conditions that did not support the wild type for lysocin production. Moreover, the engineered strain produced multiple new lysocin congeners. The determination of the lysocin BGC and the Lysobacter promoters will facilitate the ongoing efforts for yield improvement and new antibiotics biosynthesis using synthetic biology strategies.
Journal of Agricultural and Food Chemistry, Apr 1, 1997
The detection of the sulfonic acid metabolites of the chloroacetanilide herbicides acetochlor, al... more The detection of the sulfonic acid metabolites of the chloroacetanilide herbicides acetochlor, alachlor, butachlor, propachlor, and, more recently, metolachlor in surface and ground water suggests that a common mechanism for dechlorination exists via the glutathione conjugation pathway. The identification of these herbicides and their metabolites is important due to growing public awareness and concern about pesticide levels in drinking water. Although these herbicides are regulated, little is known about the fate of their metabolites in soil. The sulfonic acid metabolites were synthesized by reaction of the parent compounds with an excess of sodium sulfite. Acetochlor, alachlor, butachlor, metolachlor, and propachlor and their sulfonic acid metabolites were studied by nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. This paper provides a direct method for the preparation and characterization of these compounds that will be useful in the analysis and study of chloracetanilide herbicides and their metabolites.
Protein biochemistry protocols typically include disulfide bond reducing agents to guard against ... more Protein biochemistry protocols typically include disulfide bond reducing agents to guard against unwanted thiol oxidation and protein aggregation. Commonly used disulfide bond reducing agents include dithiothreitol, β-mercaptoethanol, glutathione, and the tris(alkyl)phosphine compounds tris(2-carboxyethyl)phosphine (TCEP) and tris(3-hydroxypropyl)phosphine (THPP). While studying the catalytic activity of the NAD(P)H-dependent enzyme Δ1-pyrroline-5-carboxylate reductase, we unexpectedly observed a rapid non-enzymatic chemical reaction between NAD+ and the reducing agents TCEP and THPP. The product of the reaction exhibits a maximum ultraviolet absorbance peak at 334 nm and forms with an apparent association rate constant of 231–491 M−1 s−1. The reaction is reversible, and nuclear magnetic resonance characterization (1H, 13C, and 31P) of the product revealed a covalent adduct between the phosphorus of the tris(alkyl)phosphine reducing agent and the C4 atom of the nicotinamide ring of NAD+. We also report a 1.45 Å resolution crystal structure of short-chain dehydrogenase/reductase with the NADP+–TCEP reaction product bound in the cofactor binding site, which shows that the adduct can potentially inhibit enzymes. These findings serve to caution researchers when using TCEP or THPP in experimental protocols with NAD(P)+. Because NAD(P)+-dependent oxidoreductases are widespread in nature, our results may be broadly relevant.
ABSTRACT The photophysical properties of a metal chelating pyridyl-based aromatic ureas and poly(... more ABSTRACT The photophysical properties of a metal chelating pyridyl-based aromatic ureas and poly(1,4-phenylene-2,6-pyridylurea) were investigated. In their solution state and upon exposure to 365 nm UV radiation, these low and high molecular weight compounds were found to cleave the urea linkage nearly quantitatively, generating the corresponding amine-terminated subunits and CO2. Through a series of model compounds along with nuclear magnetic resonance (NMR), UV/vis absorption, and fluorescence spectroscopy characterization, the photocleavage process was delineated as a function of UV dose, O2, and water. The presence of water was found crucial to this photocleavage process with O2 playing a role only in subsequent oxidation of resulting amine functionalities. The experimental results support a light-assisted hydrolysis of the urea bond as the most plausible photocleavage mechanism. The photocleavage of such pyridyl-based ureas can potentially find usages in light-assisted base generation and/or for releasing metal cations.
To determine changes in the grain components between historical and modern wheat (Triticum aestiv... more To determine changes in the grain components between historical and modern wheat (Triticum aestivum L.) cultivars, wholemeal flours from 19 wheat cultivars and 2 landraces released or introduced between 1870 and 2013 and grown over two crop years were extracted using hydroalcoholic solution and analyzed using one dimensional 1 H NMR spectral profiling. Grain yield, grain volume weight (GVW), and grain protein concentration were also measured. Grain yield increased while protein concentration decreased by release year (p < 0.001). Increasing trends (p < 0.01) were observed for tryptophan, sum of the measured amino acids, chlorogenic acid, ferulic acid, vanillic acid, and sum of the measured phenolic acids. Grain yield, phenolic acids, and tryptophan were mainly associated with modern cultivars, whereas grain protein concentration and GVW were associated with historical cultivars. The findings from this study showed changes in concentration of grain components over a century of breeding that may have implications for grain quality and human health.
This study used multiple chemical-rheological tests to investigate the long-term characteristics ... more This study used multiple chemical-rheological tests to investigate the long-term characteristics of rejuvenating agents in reclaimed asphalt binders. To this end, a base binder and its blending with an extracted binder obtained from recycled asphalt pavements were selected, and two different types of rejuvenating agents: agriculture-based and petroleum-based agents were used to modify the blended binder. The base binder and the blended binders that were modified by the two rejuvenators were then aged using a typical laboratory long-term aging procedure. The chemical studies included: a saturates-aromatics-resins-asphaltenes analysis, Fourier transform infrared spectroscopy, and elemental (carbon, hydrogen, nitrogen, sulfur and oxygen) analysis. The rheological tests primarily investigated the linear viscoelastic properties through aging and rejuvenation. The effects of rejuvenators on restoration were quite material-dependent, which was related to the different chemical compositions of the rejuvenators and their chemical-molecular interactions with the parent binder. The tests and analysis results showed that the immediate effects of rejuvenators are mostly the result of the addition of lighter molecules in rejuvenators, while the long-term effects were material-specific and further chemistry-driven. From the two rejuvenating agents studied herein, the petroleum-based material improves performance of the binder in the next round of service by preserving the chemical composition and maintaining the
ABSTRACT We have prepared a series of indocyanine green dicarboxylic acid derivatives (9a,b, 4, 1... more ABSTRACT We have prepared a series of indocyanine green dicarboxylic acid derivatives (9a,b, 4, 10, 13) with modified polyene linkers in an attempt to increase the structural rigidity of the polyene linker and thereby the fluorescent yield. Incorporation of five- and six-membered rings into the polyene system led to lower florescent yield for 9a,b, 4 and 10, but shortening the chain by two carbon atoms led to an increase in fluorescent yield for 13.
Chemical shifts are reported in units of parts per million (ppm). IR spectra were recorded on an ... more Chemical shifts are reported in units of parts per million (ppm). IR spectra were recorded on an FT-IR spectrometer. GC/MS spectra were obtained on a gas chromatograph equipped with a HP-1 methyl silicon column and detected on a low-resolution 5970 series mass selective detector. High resolution mass spectra were obtained on a micrOTOF instrument. Column chromatography was performed using silica gel, 40 microns flash silica. Thin layer chromatography was performed on silica gel (Silica Gel 60 F 254) glass plates, and the compounds were visualized by UV and 5% solution of phosphomolybdic acid in 95% EtOH.
Porphyromonas gingivalis , a recognized periodontal pathogen, synthesizes free ceramides as well ... more Porphyromonas gingivalis , a recognized periodontal pathogen, synthesizes free ceramides as well as other phosphorylated ceramide lipids. The purpose of this study was to separate complex lipids of P. gingivalis by high-performance liquid chromatography (HPLC) and determine the structures and biological activities of the major ceramide classes. Using gas chromatography-mass spectrometry, electrospray tandem mass spectrometry (ESI-MS/MS) and NMR analyses, three major classes of dihydroceramides were identified in specific HPLC fractions, with all classes containing the same dihydroceramide base structures (3-OH iso C 17:0 in amide linkage to saturated long-chain bases of 17, 18, or 19 carbons). The free dihydroceramide class recovered in HPLC fractions 7-8 revealed little biological activity. HPLC fraction 20 dihydroceramides, substituted with 1-O-phosphoglycerol and iso C 15:0 linked to the hydroxyl of 3-OH iso C 17:0 , significantly potentiated interleukin-1  (IL-1 )-mediated prostaglandin secretion and produced marked alterations in fibroblast morphology. HPLC fraction 28 dihydroceramides, substituted with 1-O-phosphoethanolamine, demonstrated little capacity to potentiate IL-1 -mediated prostaglandin secretion. The novel phosphorylated dihydroceramides synthesized by P. gingivalis demonstrate varying biological activities based on the phosphorylated head group substitution and/or the addition of esterified fatty acid. These results also demonstrate the strong virulence capacity of phosphoglycerol dihydroceramides of P. gingivalis to promote inflammatory factor secretion from IL-1 -treated fibroblasts and to produce marked alterations in cell morphology in culture.-Nichols, F. C., B.
In the present contribution, the intrinsic dynamics of the Alq3 molecule has been studied using t... more In the present contribution, the intrinsic dynamics of the Alq3 molecule has been studied using two dimensional exchange NMR spectroscopy. The understanding of the intrinsic internal dynamics of the Alq3 complex provides the basis for future studies of dynamic processes. This information will contribute towards understanding both the processing and degradation of Alq3 based organic LED devices.
The inhibition of sialyl Lewis X can prevent unwanted cellular extravasation that is associated w... more The inhibition of sialyl Lewis X can prevent unwanted cellular extravasation that is associated with inflammatory diseases and tumor metastasis. Described is an efficient methodology to prepare peracetylated GlcNAcβ3Gal-aglycone disaccharides subsequently used as metabolic decoys to inhibit sialyl Lewis X expression. Four glycosides were synthesized from one single parent disaccharide that in turn was prepared by large-scale enzymatic synthesis. The
Journal of Pharmaceutical and Biomedical Analysis, Sep 1, 1995
19F NMR spectroscopy of a model fluoroquinolone, lomefloxacin, in an erythrocyte suspension showe... more 19F NMR spectroscopy of a model fluoroquinolone, lomefloxacin, in an erythrocyte suspension showed separate resonances for the intra- and extra-cellular compartments. The intra-cellular peak revealed significant line broadening of the fluorine signals of lomefloxacin. Line broadening also occurred in the presence of oxyhemoglobin (HbO2), hematin, globin and iron. This evidence indicated that lomefloxacin interacted with these compounds; however, ultrafiltration experiments indicated that there was only weak binding (5%) of lomefloxacin to HbO2. 19F and 31P NMR spectroscopy revealed that lomefloxacin may compete with 2,3-diphosphoglycerate for its binding site on HbO2. An apparent partition coefficient of 1.90 +/- 0.15 was observed for lomefloxacin in human erythrocytes, utilizing LC analysis.
The polymer PEDOT + (1 or 2) mediates a cyclodehydration reaction with alditols 3, 5, 7, 9, in hy... more The polymer PEDOT + (1 or 2) mediates a cyclodehydration reaction with alditols 3, 5, 7, 9, in hydrocarbon solvents, to give cyclic ethers 4, 6, 8, or 10, respectively, in high yield with a trivial isolation protocol. Polymers 1 or 2 also mediate the cyclodehydration of ketohexoses such as D-fructose, but not aldohexoses, to the important industrial intermediate 5-hydroxymethylfurfural (17), under milder conditions when compared to reactions mediated by mineral acids. A cascade reaction with ketohexoses is observed in toluene via cyclodehydration followed by Friedel-Crafts alkylation of the initially formed benzylic alcohol to give 16.
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