Category: 57044-25-4

Gential, Geoffroy P. P. published the artcileSynthesis and evaluation of fluorescent Pam₃Cys peptide conjugates, HPLC of Formula: 57044-25-4, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(15), 3641-3645, database is CAplus and MEDLINE.

Chirally pure R- and S-epimers of TLR2 ligand Pam₃CysSK₄ were prepared and sep. conjugated to an OVA model epitope, in which lysine was replaced by azidonorleucine. The azide function in the conjugate permitted labeling with different fluorophores by use of strain-promoted 3+2 cycloaddition The R-epimer of the labeled conjugates induced TLR2-dependent DC maturation, while S-epimer proved to be inactive. Combining the lipophilicity of Pam₃CysSK₄ ligand with fluorophores influenced the solubility of the resulting conjugates in an unpredictable way and only the conjugates labeled with Cy-5 were suitable for confocal fluorescence microscopy experiments It was shown that both epimers of the Cy-5 labeled lipopeptides were internalized equally well, indicating TLR2-independent cellular uptake. The presented results demonstrate the usefulness of strain-promoted azide-alkyne cycloaddition in the labeling of highly lipophilic lipopeptides without disturbing the in vitro activity of these conjugates with respect to activation of TLR-2.

Bioorganic & Medicinal Chemistry Letters published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, HPLC of Formula: 57044-25-4.

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

Liu, Jia published the artcileAphadilactones A-D, four diterpenoid dimers with DGAT inhibitory and antimalarial activities from a Meliaceae plant, Name: (R)-Oxiran-2-ylmethanol, the publication is Journal of Organic Chemistry (2014), 79(2), 599-607, database is CAplus and MEDLINE.

Aphadilactones A-D isolated from Aphanamixis grandifolia (Meliaceae) are 4 diastereoisomers with an unprecedented carbon skeleton. Their challenging structures and absolute configurations were determined by a combination of spectroscopic data, chem. degradation, fragment synthesis, exptl. CD spectra, and ECD calculations The aphadilactones A-D and their oxidative products were tested for DGAT inhibitory activities in vitro. Aphadilactone C with the 5S,11S,5’S,11’S configuration had potent and selective inhibition against diacylglycerol O-acyltransferase-1 (DGAT-1; IC₅₀ = 0.46 μM; selectivity index >217). Thus, aphadilactone C is the strongest natural DGAT-1 inhibitor discovered to date. The aphadilactones A-D also had significant antimalarial activities against Plasmodium falciparum with in vitro IC₅₀ values of 190, 1350, 170, and 120 nM, resp.

Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Name: (R)-Oxiran-2-ylmethanol.

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

Willwacher, Jens published the artcileTotal Synthesis, Stereochemical Revision, and Biological Reassessment of Mandelalide A: Chemical Mimicry of Intrafamily Relationships, Product Details of C3H6O2, the publication is Chemistry – A European Journal (2015), 21(29), 10416-10430, database is CAplus and MEDLINE.

Mandelalide A and three congeners had recently been isolated as the supposedly highly cytotoxic principles of an ascidian collected off the South African coastline. Since these compounds are hardly available from the natural source, a concise synthesis route was developed, targeting one structure as the purported representation of mandelalide A. The sequence involves an iridium-catalyzed two-directional Krische allylation and a cobalt-catalyzed carbonylative epoxide opening as entry points for the preparation of the major building blocks. The final stages feature the first implementation of terminal acetylene metathesis into natural product total synthesis, which is remarkable in that this class of substrates had been beyond the reach of alkyne metathesis for decades. Synthetic mandelalide A, however, proved not to be identical with the natural product. In an attempt to clarify this issue, NMR spectra were simulated for 20 conceivable diastereomers by using DFT followed by DP4 anal.; however, this did not provide a reliable assignment either. The puzzle was ultimately solved by the preparation of three diastereomers, of which one compound proved identical with mandelalide A in all anal. and spectroscopic regards. As the entire northern sector about the THF ring in that compound shows the opposite configuration of what had originally been assigned, it is highly likely that the stereostructures of the sister compounds mandelalides B-D must be corrected analogously; we propose that these natural products are accurately represented by addnl. structures. In an attempt to prove this reassignment, an entry into mandelalides C and D was sought by subjecting an advanced intermediate of the synthesis of 6 to a largely unprecedented intramol. Morita-Baylis-Hillman reaction, which furnished the γ-lactone derivative 74 as a mixture of diastereomers. Whereas (24R)-74 was amenable to a hydroxyl-directed dihydroxylation by using OsO₄/TMEDA as the reagent, the sister compound (24S)-74 did not follow a directed path but simply obeyed Kishi’s rule; only this unexpected escape precluded the preparation of mandelalides C and D by this route. A combined spectroscopic and computational (DFT) study showed that the reasons for this strikingly different behavior of the two diastereomers are rooted in their conformational peculiarities. This aspect apart, our results show that the OsO₄/TMEDA complex reacts preferentially with electron deficient double bonds even if other alkenes are present that are more electron rich and less encumbered. Finally, in a brief biol. survey authentic mandelalide A was found to exhibit appreciable cytotoxicity only against one out of three tested human cancer cell lines and all synthetic congeners were hardly active. No significant fungicidal properties were observed The proposed new structure was (1R,3R,4E,6Z,9R,10R,12R,13R,15R,18E,21S,23R)-23-[(6-deoxy-2-O-methyl-α-L-mannopyranosyl)oxy]-13-hydroxy-15-(hydroxymethyl)-3,10-dimethyl-16,25,26-trioxatricyclo[19.3.1.1^9,12]hexacosa-4,6,18-trien-17-one for mandelalide A.

Chemistry – A European Journal published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C15H20O6, Product Details of C3H6O2.

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

Kurogome, Yuji published the artcileSynthesis of Decytospolide A, B and Their C-3 Epimers Using Stereoselective Oxypalladation, Quality Control of 57044-25-4, the publication is Synthesis (2016), 48(5), 765-771, database is CAplus.

Stereoselective synthesis of decytospolide A and B (I and II, resp.) and their C-3 epimers, which have a 2,6-cis-tetrahydropyran ring, has been achieved in high stereoselectivity and yield. The oxypalladation of single diastereomers of 6-(benzyloxy)-7-hydroxydodec-2-enyl 2-naphthoates was optimized to give products with a 2,6-cis-tetrahydropyran ring with high diastereoselectivity and yield.

Synthesis published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Quality Control of 57044-25-4.

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

Withall, David M. published the artcileStereochemistry and Mechanism of Undecylprodigiosin Oxidative Carbocyclization to Streptorubin B by the Rieske Oxygenase RedG, Application In Synthesis of 57044-25-4, the publication is Journal of the American Chemical Society (2015), 137(24), 7889-7897, database is CAplus and MEDLINE.

The prodiginines are a group of specialized metabolites that share a 4-methoxypyrrolyldipyrromethene core structure. Streptorubin B is a structurally remarkable member of the prodiginine group produced by Streptomyces coelicolor A3(2) and other actinobacteria. It is biosynthesized from undecylprodigiosin by an oxidative carbocyclization catalyzed by the Rieske oxygenase-like enzyme RedG. Undecylprodigiosin derives from the RedH-catalyzed condensation of 2-undecylpyrrole and 4-methoxy-2, 2′-bipyrrole-5-carboxaldehyde (MBC). To probe the mechanism of the RedG-catalyzed reaction, we synthesized 2-(5-pentoxypentyl)-pyrrole, an analog of 2-undecylpyrrole with an oxygen atom next to the site of C-C bond formation, and fed it, along with synthetic MBC, to Streptomyces albus expressing redH and redG. This resulted in the production of the 6′-oxa analog of undecylprodigiosin. In addition, a small amount of a derivative of this analog lacking the n-pentyl group was produced, consistent with a RedG catalytic mechanism involving hydrogen abstraction from the alkyl chain of undecylprodigiosin prior to pyrrole functionalization. To investigate the stereochem. of the RedG-catalyzed oxidative carbocyclization, [7′-²H](7’R)-2-undecylpyrrole and [7′-²H](7’S)-2-undecylpyrrole were synthesized and fed sep., along with MBC, to S. albus expressing redH and redG. Anal. of the extent of deuterium incorporation into the streptorubin B produced in these experiments showed that the pro-R hydrogen atom is abstracted from C-7′ of undecylprodigiosin and that the reaction proceeds with inversion of configuration at C-7′. This contrasts sharply with oxidative heterocyclization reactions catalyzed by other nonheme iron-dependent oxygenase-like enzymes, such as isopenicillin N synthase and clavaminate synthase, which proceed with retention of configuration at the carbon center undergoing functionalization.

Journal of the American Chemical Society published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C13H26N2, Application In Synthesis of 57044-25-4.

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

Novotny, Chris J. published the artcileFarnesyltransferase-Mediated Delivery of a Covalent Inhibitor Overcomes Alternative Prenylation to Mislocalize K-Ras, Application In Synthesis of 57044-25-4, the publication is ACS Chemical Biology (2017), 12(7), 1956-1962, database is CAplus and MEDLINE.

Mutationally activated Ras is one of the most common oncogenic drivers found across all malignancies, and its selective inhibition has long been a goal in both pharma and academia. One of the oldest and most validated methods to inhibit overactive Ras signaling is by interfering with its post-translational processing and subsequent cellular localization. Previous attempts to target Ras processing led to the development of farnesyltransferase inhibitors, which can inhibit H-Ras localization but not K-Ras due to its ability to bypass farnesyltransferase inhibition though alternative prenylation by geranylgeranyltransferase. Here the authors present the creation of a neo-substrate for farnesyltransferase that prevents the alternative prenylation by geranylgeranyltransferase and mislocalizes oncogenic K-Ras in cells.

ACS Chemical Biology published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Application In Synthesis of 57044-25-4.

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

Ding, Feiqing published the artcileSquaryl group modified phosphoglycolipid analogs as potential modulators of GPR55, Safety of (R)-Oxiran-2-ylmethanol, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(61), 8470-8473, database is CAplus and MEDLINE.

Lysophosphatidyl glucoside (LPGlc) is a structurally unique glycolipid that acts as a guidance cue for extending axons during central nervous system development by activating the class A G protein coupled receptor (GPR) 55 of spinal cord sensory axons. GPR55 not only plays an important role during development, but is also implicated in many disease states, rendering mols. that target GPR55 of widespread interest. In this study, we developed synthetic access to a novel class of LPGlc analogs featuring a squaryl diamide group as surrogate for the phosphodiester. We report the facile synthesis of a series of LPGlc analogs, their GPR dependent biol. activity and a systematic anal. of the structure-activity relationship in regards to GPR55 modulation. The lead compound featuring identical configuration at all stereo-centers compared to natural LPGlc exhibits an activity to repel axons of dorsal root ganglion (DGR) nociceptive neurons.

Chemical Communications (Cambridge, United Kingdom) published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Safety of (R)-Oxiran-2-ylmethanol.

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

Alliot, Julien published the artcileA straightforward enantioselective synthesis of F17807, Quality Control of 57044-25-4, the publication is Tetrahedron (2015), 71(50), 9383-9387, database is CAplus.

An efficient approach for the enantioselective synthesis of the 1,4-benzodioxane F17807 drug is reported. The developed route relied on two key steps, namely S_NAr and Mitsunobu reactions, which permitted a straightforward access to the title compound with full preservation of the enantiomeric excess throughout the synthetic sequence.

Tetrahedron published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Quality Control of 57044-25-4.

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

Luo, Min published the artcileInvading Escherichia coli genetics with a xenobiotic nucleic acid carrying an acyclic phosphonate backbone (ZNA), Application In Synthesis of 57044-25-4, the publication is Journal of the American Chemical Society (2019), 141(27), 10844-10851, database is CAplus and MEDLINE.

A synthetic orthogonal polymer embracing a chiral acyclic-phosphonate backbone [(S)-ZNA] is presented that uniquely adds to the emerging family of xenobiotic nucleic acids (XNAs). (S)-ZNA consists of reiterating six-atom structural units and can be accessed in few synthetic steps from readily available phophonomethylglycerol nucleoside (PMGN) precursors. Comparative thermal stability experiments conducted on homo- and heteroduplexes made of (S)-ZNA are described that evince its high self-hybridization efficiency in contrast to poor binding of natural complements. Although preliminary and not conclusive, CD data and dynamic modeling computations provide support to a left-handed geometry of double-stranded (S)-ZNA. Nonetheless, PMGN diphosphate monomers were recognized as substrates by Escherichia coli polymerase I as well as being imported into E. coli cells equipped with an algal nucleotide transporter. A further investigation into the in vivo propagation of (S)-ZNA culminated with the demonstration of the first synthetic nucleic acid with an acyclic backbone that can be transliterated to DNA by the E. coli cellular machinery.

Journal of the American Chemical Society published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Application In Synthesis of 57044-25-4.

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

Luo, Min published the artcileAmidate Prodrugs of Cyclic 9-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]adenine with Potent Anti-Herpesvirus Activity, SDS of cas: 57044-25-4, the publication is ACS Medicinal Chemistry Letters (2018), 9(4), 381-385, database is CAplus and MEDLINE.

A series of amidate prodrugs I of cyclic 9-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine (cHPMPA) featuring different amino acid motifs were synthesized. All phosphonamidates derived from (S)-cHPMPA displayed a broad spectrum activity against herpesviruses with EC₅₀ values in the low nanomolar range. A phosphonobisamidate prodrug of (S)-HPMPA also exhibited a remarkably potent antiviral activity. In addition, the leucine ester prodrug of (S)-cHPMPA and phosphonobisamidate valine ester prodrug of (S)-HPMPA proved stable in human plasma. These data warrant further development of cHPMPA prodrugs, especially against human cytomegalovirus (HCMV), for which there is a high need for treatment in transplant recipients.

ACS Medicinal Chemistry Letters published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, SDS of cas: 57044-25-4.

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