Template‐Directed Incorporation of Functional Molecules into DNA DOI
Zeynep Kanlıdere

ChemBioChem, Journal Year: 2022, Volume and Issue: 24(4)

Published: Dec. 15, 2022

Abstract We report a versatile method for the incorporation of functional molecules into oligonucleotides carrying reactive groups by using template‐directed postsynthetic approach in solution phase. For this purpose, we prepared an amino group on backbone acylic threoninol scaffold. The resulting could be used to introduce almost any molecule aldehyde, which can be, among other things, metal‐binding ligand or fluorophore. In our study, incorporated aldehyde‐bearing phenanthroline, ligand, reversible conjugation. observed that use abasic sugar site instead natural nucleobase template strand increased yield conjugation and induced selective phenanthroline. This lead progress development probes recognition regions duplex DNA. Moreover, formation metal ligand‐oligonucleotide conjugates might have potential applications hybrid biocatalysis enantioselective transformations.

Language: Английский

DNA-metal composites as bioinspired catalysts in chemical reactions DOI
Leila Hadian-Dehkordi,

Zeinab Abdi,

Armin Zarei

et al.

Coordination Chemistry Reviews, Journal Year: 2024, Volume and Issue: 505, P. 215635 - 215635

Published: Feb. 9, 2024

Language: Английский

Citations

8
Single-Handed Helical Polymer-Based Polycarboxylate with Achiral Triarylphosphine Pendants as Chiral Catalysts for Asymmetric Cross-Coupling Reactions in Pure Water DOI

Naoaki Kamiya,

Takuma Kuroda,

Yuuya Nagata

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

Helical poly(quinoxaline-2,3-diyl)s (PQX) containing chiral carboxylic acid side chains derived from natural l-lactic were synthesized. The newly synthesized helical polycarboxylated polymer was soluble in basic pure water by forming polycarboxylate and adopted the P-helical conformation (right-handed), whereas M-helical is predominant under weakly acidic aqueous conditions. water-soluble PQX additional monomer units bearing a 2-(diarylphosphino)phenyl group employed asymmetric Suzuki-Miyaura coupling reaction absence of organic cosolvents. Remarkable enantioselectivities up to 99% ee, which found be higher than same solvent using corresponding lipophilic PQX, obtained for couplings 2-substituted 1-halonaphthalenes. It presumed that hydrophobic environment provided main chain according Nile Red-based hydrophobicity test. Recovery crude product without any trace has been demonstrated switch solubility depending on pH.

Language: Английский

Citations

0
Nickel-Catalyzed One-Pot H/D Exchange and Asymmetric Michael Addition in the Presence of D2O DOI

Junyu Zhou,

Yuxiang Zhang, Jing Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

A step-economical and efficient strategy for the enantioselective synthesis of tetradeuterated γ-nitroketones using a cost-effective readily available deuterium source is highly desirable. Herein, we report nickel-catalyzed one-pot H/D exchange Michael addition α,β-unsaturated 2-acyl imidazoles with nitromethane in presence D2O. This protocol demonstrates excellent efficiency, high enantioselectivity, broad substrate scope, offering practical versatile approach to accessing deuterium-labeled compounds.

Language: Английский

Citations

0
Recent advances in enzymatic carbon–carbon bond formation DOI Creative Commons
Hua Zhao

RSC Advances, Journal Year: 2024, Volume and Issue: 14(36), P. 25932 - 25974

Published: Jan. 1, 2024

Enzymatic carbon-carbon (C-C) bond formation reactions have become an effective and invaluable tool for designing new biological medicinal molecules, often with asymmetric features. This review provides a systematic overview of key C-C enzymes, the focus reaction mechanisms recent advances. These include aldol reaction, Henry Knoevenagel condensation, Michael addition, Friedel-Crafts alkylation acylation, Mannich Morita-Baylis-Hillman (MBH) Diels-Alder acyloin condensations

Language: Английский

Citations

2
Expanding the ‘aplysinospin cascade’ through DNA-templated [2+2] photocycloaddition DOI Creative Commons
Samuel Oger, Nicolas Duchemin,

Yara Mayssa Bendiab

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(28), P. 4221 - 4224

Published: Jan. 1, 2023

Inspired by the unique ability of nucleic acids to template chemical transformations that are otherwise impossible in solution, we embarked on generalisation our DNA-templated [2+2] photo-induced homo- and heterodimerization aplysinopsins. Our process ensures a straightforward access cyclobutane containing natural products analogues thereof. Most importantly, this conceptual biomimetic achievement presents interesting arguments build biosynthetic scenario.

Language: Английский

Citations

6
An Intramolecular Radical C–N Coupling by N-Iodosuccinimide DOI
Shyamal Kanti Bera, Rosalin Bhanja, Prasenjit Mal

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 56(04), P. 585 - 596

Published: March 27, 2023

Abstract A useful method for the formation of benzimidazole-fused phenanthridines through an intramolecular coupling unactivated C(sp2)–H and N(sp3)–H bonds using N-iodosuccinimide (NIS) in trifluoroethanol (TFE) is presented. The synthesis benzo[4,5]imidazo[1,2-f]phenanthridines from 2-([1,1′-biphenyl]-2-yl)-1H-benzo[d]imidazole derivatives mild, efficient, sustainable, with high yields minimal waste generation. control experiments EPR studies were aimed at rationalizing radical pathway reaction. Specifically, use 1,1-diphenylethylene, TEMPO, BHT, DMPO as a free-radical spin-trapping reagent studies, allowed us to conceive pathway. gram-scale further supported practical utility methodology field synthetic chemistry.

Language: Английский

Citations

6
Cyclic Dinucleotide-Based Enantioselective Fluorination in Water DOI Open Access
Xingchen Dong,

Shuting Lv,

Qianqian Qi

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(1), P. 189 - 197

Published: Dec. 22, 2022

The diverse structures of DNA serve as potent chiral scaffolds for DNA-based asymmetric catalysis, yet in most cases tens to hundreds nucleotides hybrid catalysts hinder the deep insight into their structure–activity relationship. Owing structural simplicity and design flexibility nucleotides, nucleotide-based have been emerging a promising way obtain fine information understand catalytic mechanisms. Herein, we found that cyclic dinucleotide di-AMP (c-di-AMP) 1,10-phenanthroline copper(II) nitrate (Cu(phen)(NO3)2) are assembled c-di-AMP-based catalyst (c-di-AMP/Cu(phen)(NO3)2), which could fast achieve enantioselective fluorination water with 90–99% yields up 90% enantiomeric excess (ee). host–guest interaction between c-di-AMP Cu(phen)(NO3)2 has proposed mainly supramolecular mode evidenced by spectroscopic techniques ultraviolet–visible, fluorescence, circular dichroism, nuclear magnetic resonance. tightly binds binding constant 1.7 ± 0.3 × 105 M–1, assembly c-di-AMP/Cu(phen)(NO3)2 shows modest rate enhancement carbon–fluorine bond formations supported kinetic studies.

Language: Английский

Citations

4
Cu(i)-catalyzed dearomatizing cascade of thiazoles using two molecules of an α-aryl-α-diazoester: a novel approach for the synthesis of densely substituted 4-thiazolines DOI
Ying Ran,

Xingrong Ye,

Mingli Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(21), P. 6117 - 6125

Published: Jan. 1, 2024

A novel copper( i )-catalyzed cascade reaction has been devised for the functionalization of thiazoles, which employs two molar equivalents an α-aryl-α-diazoester.

Language: Английский

Citations

0
Merging DNA Repair with Bioorthogonal Conjugation Enables Accessible and Versatile Asymmetric DNA Catalysis DOI

Jie Sheng,

Zhaoyang Li,

Kelly Kar Yun Koh

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(24), P. 16531 - 16539

Published: June 11, 2024

Optimizing catalysts through high-throughput screening for asymmetric catalysis is challenging due to the difficulty associated with assembling a library of catalyst analogues in timely fashion. Here, we repurpose DNA excision repair and integrate it bioorthogonal conjugation construct diverse array hybrid highly accessible catalysis, enabling dramatically expedited optimization process, superior reactivity selectivity, as well first atroposelective catalysis. The bioorthogonality this strategy ensures exceptional tolerance toward functional groups, thereby facilitating facile construction 44 bearing various unprotected groups. This unique feature holds potential enable catalytic modalities that were previously deemed unattainable.

Language: Английский

Citations

0
Template‐Directed Incorporation of Functional Molecules into DNA DOI
Zeynep Kanlıdere

ChemBioChem, Journal Year: 2022, Volume and Issue: 24(4)

Published: Dec. 15, 2022

Abstract We report a versatile method for the incorporation of functional molecules into oligonucleotides carrying reactive groups by using template‐directed postsynthetic approach in solution phase. For this purpose, we prepared an amino group on backbone acylic threoninol scaffold. The resulting could be used to introduce almost any molecule aldehyde, which can be, among other things, metal‐binding ligand or fluorophore. In our study, incorporated aldehyde‐bearing phenanthroline, ligand, reversible conjugation. observed that use abasic sugar site instead natural nucleobase template strand increased yield conjugation and induced selective phenanthroline. This lead progress development probes recognition regions duplex DNA. Moreover, formation metal ligand‐oligonucleotide conjugates might have potential applications hybrid biocatalysis enantioselective transformations.

Language: Английский

Citations

1