Category: alcohols-buliding-blocks

Luo, Chengyi published the artcileEfficient biodegradation of phenanthrene using Pseudomonas stutzeri LSH-PAH1 with the addition of sophorolipids: Alleviation of biotoxicity and cometabolism studies, Formula: C11H8O3, the publication is Environmental Pollution (Oxford, United Kingdom) (2022), 119011, database is CAplus and MEDLINE.

Phenanthrene (PHE) is widely distributed, and it can cause genotoxicity in humans by interacting with enzymes in the body. A current challenge for PHE bioremediation is the inhibitory effect of biotoxic intermediates on bacterial growth. Notably, the aerobic biotransformation processes for PHE in the presence of sophorolipids have been poorly studied. Here, a PHE-degrading strain was isolated from sediments and identified as Pseudomonas stutzeri and named LSH-PAH1. It was observed that 1-naphthol (a biotoxic substance that can inhibit strain growth) was produced during the PHE metabolism process of LSH-PAH1. The biodegradation ratio increased from 21.4% to 91.7% within 48 h after the addition of sophorolipids. Unexpectedly, this addition accelerated the metabolic process for 1-naphthol rather than causing its accumulation. The cometabolism of 1-naphthol and sophorolipids alleviated the biotoxic effects for the strain, which was verified by gene expression anal. We identified a new PHE-degrading strain and provided a mechanism for PHE biodegradation using LSH-PAH1 with the addition of sophorolipids, which provides a reference for practical applications of the bioremediation of PHE and study of the cometabolism of biotoxic intermediates.

Environmental Pollution (Oxford, United Kingdom) published new progress about 86-48-6. 86-48-6 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment,Natural product, name is 1-Hydroxy-2-naphthoic acid, and the molecular formula is C11H8O3, Formula: C11H8O3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gao, Lili published the artcileStepwise metabolic engineering of Gluconobacter oxydans WSH-003 for the direct production of 2-keto-L-gulonic acid from D-sorbitol, Recommanded Product: (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, the publication is Metabolic Engineering (2014), 30-37, database is CAplus and MEDLINE.

2-Keto-L-gulonic acid (2-KLG), the direct precursor of vitamin C, is currently produced by a two-step fermentation route from D-sorbitol. However, this route involves three bacteria, making the mix-culture system complicated and redundant. Thus, replacement of the conventional two-step fermentation process with a one-step process could be revolutionary in vitamin C industry. In this study, different combinations of five L-sorbose dehydrogenases (SDH) and two L-sorbosone dehydrogenases (SNDH) from Ketogulonicigenium vulgare WSH-001 were introduced into Gluconobacter oxydans WSH-003, an industrial strain used for the conversion of D-sorbitol to L-sorbose. The optimum combination produced 4.9 g/L of 2-KLG. In addition, 10 different linker peptides were used for the fusion expression of SDH and SNDH in G. oxydans. The best recombinant strain (G. oxydans/pGUC-k0203-GS-k0095) produced 32.4 g/L of 2-KLG after 168 h. Furthermore, biosynthesis of pyrroloquinoline quinine (PQQ), a cofactor of those dehydrogenases, was enhanced to improve 2-KLG production With the stepwise metabolic engineering of G. oxydans, the final 2-KLG production was improved to 39.2 g/L, which was 8.0-fold higher than that obtained using independent expression of the dehydrogenases. These results bring us closer to the final one-step industrial-scale production of vitamin C.

Metabolic Engineering published new progress about 526-98-7. 526-98-7 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Other Sugar Units, name is (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, and the molecular formula is C6H10O7, Recommanded Product: (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Moe, Luke A. published the artcileRemarkable Aliphatic Hydroxylation by the Diiron Enzyme Toluene 4-Monooxygenase in Reactions with Radical or Cation Diagnostic Probes Norcarane, 1,1-Dimethylcyclopropane, and 1,1-Diethylcyclopropane, Application of 1-Methylcyclobutan-1-ol, the publication is Biochemistry (2004), 43(50), 15688-15701, database is CAplus and MEDLINE.

Toluene 4-monooxygenase (T4MO) catalyzes the hydroxylation of toluene to yield 96% p-cresol. This diiron enzyme complex was used to oxidize norcarane (bicyclo[4.1.0]heptane), 1,1-dimethylcyclopropane, and 1,1-diethylcyclopropane, substrate analogs that can undergo diagnostic reactions upon the production of transient radical or cationic intermediates. Norcarane closely matches the shape and volume of the natural substrate toluene. Reaction of isoforms of the hydroxylase component of T4MO (T4moH) with different regiospecificities for toluene hydroxylation (k_cat ≈ 1.9-2.3 s^-1 and coupling efficiency ≈ 81-96%) revealed similar catalytic parameters for norcarane oxidation (k_cat ≈ 0.3-0.5 s^-1 and coupling efficiency ≈ 72%). The products included variable amounts of the un-rearranged isomeric norcaranols and cyclohex-2-enyl methanol, a product attributed to rearrangement of a radical oxidation intermediate. A ring-expansion product derived from the norcaranyl C-2 cation, cyclohept-3-enol, was not produced by either the natural enzyme or any of the T4moH isoforms tested. Comparative studies of 1,1-dimethylcyclopropane and 1,1-diethylcyclopropane, diagnostic substrates with differences in size and with ∼50-fold slower k_cat values, gave products consistent with both radical rearrangement and cation ring expansion. Examination of the isotopic enrichment of the incorporated O-atoms for all products revealed high-fidelity incorporation of an O-atom from O₂ in the un-rearranged and radical-rearranged products, while the O-atom found in the cation ring-expansion products was predominantly obtained by reaction with H₂O. The results show a divergence of radical and cation pathways for T4moH-mediated hydroxylation that can be dissected by diagnostic substrate probe rearrangements and by changes in the source of oxygen used for substrate oxygenation.

Biochemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Application of 1-Methylcyclobutan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ruzicka, Frank published the artcileMethane monooxygenase catalyzed oxygenation of 1,1-dimethylcyclopropane. Evidence for radical and carbocationic intermediates, COA of Formula: C5H10O, the publication is Biochemistry (1990), 29(7), 1696-700, database is CAplus and MEDLINE.

Methane monooxygenase of Methylosinus trichosporium catalyzes the oxygenation of 1,1-dimethylcyclopropane in the presence of O₂ and NADH to (1-methylcyclopropyl)methanol(81%), 3-methyl-3-buten-1-ol (6%), and 1-methylbutanol (13%). Oxygenation by ¹⁸O₂ using the purified enzyme proceeds with incorporation of ¹⁸O into the products. Inasmuch as methane monooxygenase catalyzes the insertion of O from O₂ into a C-H bond of alkanes, (1-methylcyclopropyl)methanol appears to be a conventional oxygenation product. 3-Methyl-3-buten-1-ol is a rearrangement product that can be rationalized on the basis that enzymic oxygenation of 1,1-dimethylcyclopropane proceeds via the (1-methylcyclopropyl)carbinyl radical, which is expected to undergo rearrangement with ring opening to the homoallylic 3-methyl-3-buten-1-yl radical in competition with conventional with ring opening to the homoallylic 3-methyl-3-butenyl-1-yl radical in competition with conventional oxygenation. Oxygenation of the latter radical gives 3-methyl-3-buten-1-ol. 1-Methylcyclobutanol is a ring-expansion product, whose formation is best explained on the basis that the 1-methylcyclobutyl tertiary carbocation is an oxygenation intermediate. This cation would result from rearrangements of carbocations derived by 1-electron oxidation of either radical intermediate. The fact that both 3-methyl-3-buten-1-ol and 1-methylcyclobutanol are produced suggests that the oxygenation mechanism involves both radical and carbocationic intermediates. Radicals and carbocations can both be intermediates if they are connected by an electron-transfer step. A reasonable reaction sequence is one in which the cofactor (μ-oxo)diiron reacts with O₂ and 2-electrons to generate a H atom-abstracting species and an oxidizing agent. The H-abstracting species might be the enzymic radical or another species generated by the Fe complex and O₂. Oxygenation then could proceed by abstraction for a H atom from the substrate to form a radical, followed by electron transfer from the radical to the oxidizing species to form a carbocation. The carbocation would be quenched by O associated with the oxygenation cofactor to generate the product.

Biochemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, COA of Formula: C5H10O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Cheng, Rui published the artcileA nucleotide-sensing endonuclease from the Gabija bacterial defense system, Name: Triisopropanolamine, the publication is Nucleic Acids Research (2021), 49(9), 5216-5229, database is CAplus and MEDLINE.

The arms race between bacteria and phages has led to the development of exquisite bacterial defense systems including a number of uncharacterized systems distinct from the well-known restriction-modification and CRISPR/Cas systems. Here, we report functional analyses of the GajA protein from the newly predicted Gabija system. The GajA protein is revealed as a sequence-specific DNA nicking endonuclease unique in that its activity is strictly regulated by nucleotide concentration NTP and dNTP at physiol. concentrations can fully inhibit the robust DNA cleavage activity of GajA. Interestingly, the nucleotide inhibition is mediated by an ATPase-like domain, which usually hydrolyzes ATP to stimulate the DNA cleavage when associated with other nucleases. These features suggest a mechanism of the Gabija defense in which an endonuclease activity is suppressed under normal conditions, while it is activated by the depletion of NTP and dNTP upon the replication and transcription of invading phages. This work highlights a concise strategy to utilize a DNA nicking endonuclease for phage resistance via nucleotide regulation.

Nucleic Acids Research published new progress about 122-20-3. 122-20-3 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment, name is Triisopropanolamine, and the molecular formula is C9H21NO3, Name: Triisopropanolamine.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Parnes, Howard published the artcileSynthesis of [¹⁴C]-labeled dihydropyridine calcium channel-entry blockers: nicardipine-[4-¹⁴C] and RS-93522-[4-¹⁴C], Synthetic Route of 101-98-4, the publication is Journal of Labelled Compounds and Radiopharmaceuticals (1988), 25(6), 621-6, database is CAplus.

The Hantzsch synthesis was used to prepare title compounds I [R = CH₂CH₂NMeCH₂Ph, CH₂CH₂C₆H₄[OCH₂CH(OH)CH₂OH]-p] from m-O₂NC₆H₄¹⁴CHO (II), H₂NCMe:CHCO₂Me, and MeCOCH₂CO₂R. II was prepared in high yield from PhBr and ¹⁴CO₂ in 4 steps.

Journal of Labelled Compounds and Radiopharmaceuticals published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C10H15NO, Synthetic Route of 101-98-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Wang, Yafeng published the artcileEnantioselective β-hydroxy thioesters formation via decarboxylative aldol reactions of malonic acid half thioesters with aldehydes promoted by chloramphenicol derived sulfonamides¹, Computed Properties of 156453-53-1, the publication is Tetrahedron (2017), 73(34), 5055-5062, database is CAplus.

A highly enantioselective synthesis of chiral β-hydroxy thioesters that uses a decarboxylative aldol reaction of malonic acid half thioesters and aldehydes catalyzed by a chloramphenicol base-derived bifunctional organocatalyst is reported. The resulting chiral β-hydroxy thioesters were obtained in high yields (up to 82%) with good to excellent enantioselectivities (up to 94% ee). The synthetic application of the methodol. is illustrated by the asym. synthesis of the selective serotonin reuptake inhibitor dapoxetine.

Tetrahedron published new progress about 156453-53-1. 156453-53-1 belongs to alcohols-buliding-blocks, auxiliary class Chiral,Benzene,Naphthalene,Alcohol,Ether, name is (R)-3-(Naphthalen-1-yloxy)-1-phenylpropan-1-ol, and the molecular formula is C15H20O6, Computed Properties of 156453-53-1.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Liao, Xia-ling published the artcileMicrostructural characterization of cement in the presence of alkanolamines, Product Details of C9H21NO3, the publication is Materials Today Communications (2021), 102386, database is CAplus.

In order to understand the potential issues regarding the cement performance over time in the presence of alkanolamines, such as triethanolamine (TEA) and triisopropanolamine (TIPA), this investigation provided a series of quant. phase characterization to monitor the hydration and microstructure of cement pastes. The addition of 0.02% alkanolamines to cement promoted the strength development and altered the hydration kinetics at early ages. The aluminate reaction was greatly promoted, which resulted in the formation of hydrosulfoaluminates with a high monosulfoaluminate-to-ettringite ratio due to the facilitated dissolution of the intermediate phase. The morphol. and chem. composition of the hydrates, as well as the porosity of the pastes, were also influenced by the altered hydration kinetics. Particularly, TIPA markedly reduced Si/Ca ratio (from 0.61 to 0.51) and increased Fe/Ca ratio (from 0.016 to 0.036) in the C-S-H gel at the early stage of hydration. Based on the variations in microstructural features subjected to the alkanolamines, the durability and long-term performance of the cement, including the phase variation, resistance to sulfate or chloride ingression and volume stability, were discussed.

Materials Today Communications published new progress about 122-20-3. 122-20-3 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment, name is Triisopropanolamine, and the molecular formula is C9H21NO3, Product Details of C9H21NO3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Bellotti, Peter published the artcileCatalytic defluorinative ketyl-olefin coupling by halogen-atom transfer, COA of Formula: C5H12O2, the publication is Chemical Science (2022), 13(26), 7855-7862, database is CAplus and MEDLINE.

A new approach to achieve catalytic ketyl-olefin coupling reactions by a halogen-atom transfer mechanism provides innovative and efficient access to various gem-difluorohomoallylic alcs. 4-OCH₃C₆H₄C(=C(F)₂)CH₂C(OC(O)C₆H₅)R [R = H, n-pentyl, cyclohexyl, 2-(4-fluorophenyl)ethyl, etc.] under mild conditions with broad substrate scope. Preliminary mechanistic exptl. and computational studies demonstrate that this radical-to-polar crossover transformation could be achieved by sequentially orchestrated Lewis acid activation, halogen-atom transfer, radical addition, single-electron reduction and β-fluoro elimination.

Chemical Science published new progress about 111-29-5. 111-29-5 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ploymers, name is Pentane-1,5-diol, and the molecular formula is C5H12O2, COA of Formula: C5H12O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Yin, Xia published the artcileIdentification of volatile and odor-active compounds in Hunan black tea by SPME/GC-MS and multivariate analysis, Synthetic Route of 106-25-2, the publication is LWT–Food Science and Technology (2022), 113656, database is CAplus.

Hunan black tea is well-known for its floral-honey aroma, but the volatile components responsible for the fragrance have not been elucidated yet. In this study, the volatile compounds in Hunan black tea were identified and quantified by the headspace solid-phase microextraction coupled with gas chromatog.-mass spectrometry (HS-SPME-GC-MS). The results showed that 88 compounds were extracted and determined in Hunan black tea, including the dominant components Geraniol, phenethyl alc., phenylacetaldehyde, linalool, nonanal and other 5 aromatic compounds Furthermore, the aroma-active compounds were identified by odor activity value (OAV). It was found that 24 aroma compounds, including geraniol with an OAV≥1 were regarded as the primary active aromatic compounds in Hunan black tea. Finally, partial least squares (PLS) regression anal. was employed and results revealed that Nonanal, trans-nerolidol, benzyl alc., and phenylethanol exhibit a pos. correlation with the intensity of floral and sweet honey aromas. Overall, this study identified the volatile compounds responsible for the dominant floral-honey aroma in Hunan black tea.

LWT–Food Science and Technology published new progress about 106-25-2. 106-25-2 belongs to alcohols-buliding-blocks, auxiliary class Natural product, name is cis-3,7-Dimethyl-2,6-Octadien-1-Ol, and the molecular formula is C10H12O5, Synthetic Route of 106-25-2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts