7348-78-9Relevant academic research and scientific papers
OLIGONUCLEOTIDE COMPOSITIONS AND METHODS THEREOF
-
Paragraph 00815; 00816, (2021/11/26)
The present disclosure provides modified oligonucleotides and compositions and methods thereof. In some embodiments, provided technologies comprise modified sugars and/or modified internucleotidic linkages. In some embodiments, the present disclosure provides technologies for preparing modified oligonucleotides. In some embodiments, the present disclosure provides chirally controlled oligonucleotide compositions and methods for their preparation and uses.
Beyond Amphiphilic Balance: Changing Subunit Stereochemistry Alters the Pore-Forming Activity of Nylon-3 Polymers
Liu, Lei,Courtney, Kevin C.,Huth, Sean W.,Rank, Leslie A.,Weisblum, Bernard,Chapman, Edwin R.,Gellman, Samuel H.
supporting information, p. 3219 - 3230 (2021/03/08)
Amphiphilic nylon-3 polymers have been reported to mimic the biological activities of natural antimicrobial peptides, with high potency against bacteria and minimal toxicity toward eukaryotic cells. Amphiphilic balance, determined by the proportions of hydrophilic and lipophilic subunits, is considered one of the most important features for achieving this activity profile for nylon-3 polymers and many other antimicrobial polymers. Insufficient hydrophobicity often correlates with weak activities against bacteria, whereas excessive hydrophobicity correlates with high toxicity toward eukaryotic cells. To ask whether factors beyond amphiphilic balance influence polymer activities, we synthesized and evaluated new nylon-3 polymers with two stereoisomeric subunits, each bearing an ethyl side chain and an aminomethyl side chain. Subunits that differ only in stereochemistry are predicted to contribute equally to amphiphilic balance, but we observed that the stereochemical difference correlates with significant changes in biological activity profile. Antibacterial activities were not strongly affected by subunit stereochemistry, but the ability to disrupt eukaryotic cell membranes varied considerably. Experiments with planar lipid bilayers and synthetic liposomes suggested that eukaryotic membrane disruption results from polymer-mediated formation of large pores. Collectively, our results suggest that factors other than amphiphilic balance influence the membrane activity profile of synthetic polymers. Subunits that differ in stereochemistry are likely to have distinct conformational propensities, which could potentially lead to differences in the average shapes of polymer chains, even when the subunits are heterochiral. These findings highlight a dimension of polymer design that should be considered more broadly in efforts to improve specificity and efficacy of antimicrobial polymers.
Visible Light-Mediated Photochemical Reactions of 2-(2′-Alkenyloxy)cycloalk-2-enones
Gra?l, Raphaela,Jandl, Christian,Bach, Thorsten
, p. 11426 - 11439 (2020/10/12)
The title compounds were prepared, and their reactivity was studied upon sensitized irradiation at λ = 420 nm. Thioxanthen-9-one was employed as the sensitizer at a loading of 10 mol % in small-scale reactions and of 2.5 mol % on a larger scale. Cyclohex-
METHODS FOR PREPARATION OF JASMONATE COMPOUNDS
-
Paragraph 045, (2019/07/20)
This invention relates to methods for preparation of jasmonate compounds via a salt of jasmonic acid.
Electrophilic rearrangements of chiral amides: A traceless asymmetric α-allylation
Peng, Bo,Geerdink, Danny,Maulide, Nuno
supporting information, p. 14968 - 14971 (2013/11/06)
A one-pot protocol for the asymmetric α-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched α-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.
A highly reusable rhodium catalyst-organic framework for the intramolecular cycloisomerization of 1,6-enynes
Corkum, Elizabeth G.,Hass, Michael J.,Sullivan, Andrew D.,Bergens, Steven H.
supporting information; experimental part, p. 3522 - 3525 (2011/09/16)
The intramolecular cycloisomerization of 1,6-enynes in 95-99% ee is reported using an immobilized Rh catalyst-organic framework synthesized from alternating ring-opening metathesis polymerization (altROMP) assembly. The framework was reused up to seven times, and it was used in high turnover number (TON) batch reactions. The catalyst provided the highest TONs to date (up to 890) for the cycloisomerizations, with catalyst loadings ranging from 0.2 to 0.06 mol %.
Protective group-free syntheses of (±)-frontalin, (±)-endo-brevicomin, (±)-exo-brevicomin, and (±)-3,4- dehydro-exo-brevicomin: Racemic pheromones with a 6,8-dioxabicyclo[3.2.1]octane ring
Mori, Kenji
body text, p. 976 - 981 (2012/01/05)
Protective group-free syntheses of four racemic pheromones with a 6,8-dioxabicyclo[3.2.1]octane ring were achieved in five or six steps from commercially available (±)-3-butyn-2-ol (6) and 2-alkenyl halides or 2-alken-1-ol by employing Lewis acid-catalyzed acetalization of δ, ε-epoxy ketones as the key reaction. (±)- Frontalin (1) was prepared in a 25% overall yield in five steps from methallyl chloride (5a), (±)-endo-brevicomin (2) was prepared in a 23% overall yield in five steps from (E)-2-pentenyl bromide (5b), and (±)-exo-brevicomin (3) and (±)-3,4-dehydro-exo-brevicomin (4) were both prepared in a 4%overall yield in six steps based on (Z)-2-penten-1-ol (12).
Unexpected electrophilic rearrangements of amides: A stereoselective entry to challenging substituted lactones
Madelaine, Claire,Valerio, Viviana,Maulide, Nuno
supporting information; experimental part, p. 1583 - 1586 (2010/06/15)
"Chemical Equation Presented" Surprise, surprise! An unexpected skeletal rearrangement was developed into a chemo- and stereoselective synthesis of aallyl and allenyl lactones with challenging substitution patterns (see scheme; EWC = electron-withdrawing group). The generality, unique features, and synthetic potential of this reaction were probed and a mechanism was proposed.
Microwave assisted synthesis of unsaturated jasmone heterocyclic analogues as new fragrant substances
Pawelczyk, Anna,Zaprutko, Lucjusz
body text, p. 3032 - 3039 (2009/10/02)
Taking the rising interest in jasmone structure based fragrant compounds into account it has been decided to take up an attempt to synthesize the new heterocyclic derivatives of this 2,3-disubstituted cyclopentenone, which could be characterized by the ability of interaction with the same receptors with which jasmone affects. Obtained structures of unsaturated heterocyclic derivatives are based on pyrrolidinone, oxazolidinone, pyrazolidinone, pyrazolone and thiazolidinone systems with 2-double or 2-triple unsaturated five-carbon side chain. The rapid, highly yielding and ecofriendly microwave assisted organic syntheses (MAOS) have been used to obtain compounds mentioned above. Odor evaluation and relationships between their structure and osmic properties for all synthesized fragrant compounds have been studied. It has been shown that the majority of the obtained compounds have exhibited interesting, very intensive and fixative fragrant properties.
Synthesis and self-photooxygenation of alkenyl-linked [60]fullerene derivatives. A regioselective ene reaction
Chronakis, Nikos,Vougioukalakis, Georgios C.,Orfanopoulos, Michael
, p. 945 - 948 (2007/10/03)
(equation presented) Alkenyl-linked C60 derivatives undergo self-photooxygenation regioselectively, by the preferential abstraction of allylic hydrogens on the fullerene side of the double bond.
