2020
DOI: 10.1002/ange.201915493
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RASS‐Enabled S/P−C and S−N Bond Formation for DEL Synthesis

Abstract: DNA encoded libraries (DEL) have shown promise as a valuable technology for democratizing the hit discovery process. Although DEL provides relatively inexpensive access to libraries of unprecedented size, their production has been hampered by the idiosyncratic needs of the encoding DNA tag relegating DEL compatible chemistry to dilute aqueous environments. Recently reversible adsorption to solid support (RASS) has been demonstrated as a promising method to expand DEL reactivity using standard organic synthesis… Show more

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Cited by 11 publications
(5 citation statements)
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“…13 Interestingly, most successful coupling reactions have resulted from electron-deficient (hetero)aryl halides except for those in Fu's and Oderinde's studies. 9,10 The same reactivity trend was also observed in Baran's studies on DEL synthesis via Ni-catalyzed C-S bond formation 14 and Lipshutz's Ni-catalyzed migita-like C-S cross-coupling in recyclable water 15 that were disclosed very recently (Fig. 1).…”
Section: Introductionsupporting
confidence: 74%
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“…13 Interestingly, most successful coupling reactions have resulted from electron-deficient (hetero)aryl halides except for those in Fu's and Oderinde's studies. 9,10 The same reactivity trend was also observed in Baran's studies on DEL synthesis via Ni-catalyzed C-S bond formation 14 and Lipshutz's Ni-catalyzed migita-like C-S cross-coupling in recyclable water 15 that were disclosed very recently (Fig. 1).…”
Section: Introductionsupporting
confidence: 74%
“…During the past two decades, great efforts have been directed to the development of catalytic systems for coupling of (hetero) aryl halides with thiols and their equivalents [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] to assemble (hetero)aryl thioethers of high prevalence in bioactive molecules 16 and synthetic intermediates. 17 Because of their abundance, relatively low cost but low reactivity, the utilization of (hetero)aryl chlorides as coupling partners has become a reference point to assess the efficiency of newly developed catalytic systems.…”
Section: Introductionmentioning
confidence: 99%
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“…Typically, building blocks (BBs) and DNA barcodes are assembled by 3 to 4 cycles of interactive enzymatic encoding and DNA compatible reactions to efficiently generate the corresponding DEL. Therefore, the development of DNA compatible reactions is one of the key issues in DEL research field [53‐66] …”
Section: Resultsmentioning
confidence: 99%
“… 5 Non-enzymatic means to form these linkages in this context are likely rare because of the heavy reliance on P(III) approaches which, due to the aforementioned hydrolytic instability and lack of chemoselectivity, makes them unsuitable for such applications. Prior work from the lab on DNA-encoded libraries 80 83 gave us a framework from which to think about the direct modification of nucleic acids using Ψ and related reagents. In particular, the use of reversible adsorption to solid support (RASS) allowed native DNA constructs to be manipulated as if they were small organic compounds.…”
Section: Leveraging P(v) Reactivity For Exquisitely Selective Bioconjugationmentioning
confidence: 99%