Reagent-Based Scaffold Diversity for DNA-Encoded Library Design: Solid Phase Synthesis of DNA-Tagged sp(3)-Rich Heterocycles by SnAP Chemistry

Reactions that require strictly dry conditions are challenging to translate to a DNA-encoded library format. Controlled pore glass solid support-connected DNA oligonucleotide-aldeh y d e conjugates could be condensed with SnAP reagents and cyclized to various sp(3)-rich heterocycles. The Boc-group o...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 6; pp. 1383 - 1387
Main Authors Skopic, Mateja Klika, Losch, Florian, McMillan, Angus E., Willeke, Niklas, Malenica, Mateo, Bering, Luis, Bode, Jeffrey, Brunschweiger, Andreas
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 18.02.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
THIOMORPHOLINES
ALDEHYDES
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Summary:Reactions that require strictly dry conditions are challenging to translate to a DNA-encoded library format. Controlled pore glass solid support-connected DNA oligonucleotide-aldeh y d e conjugates could be condensed with SnAP reagents and cyclized to various sp(3)-rich heterocycles. The Boc-group of products provided a handle for product purification, and its facile removal under acidic conditions was tolerated by a chemically stabilized barcode. The reaction provides reagent-based scaffold diversity with functionalities for further library synthesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00228