DNA-associated click chemistry

Haque, Mohammad Mojibul; Peng, Xiaohua

doi:10.1007/s11426-013-5035-1

Cited by 27 publications

(15 citation statements)

References 77 publications

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“…The scaffolds each contained a protected primary amine group and an azide moiety. Using a split‐and‐pool protocol, featuring the reaction of amines with carboxylic acids or the copper(I)‐catalyzed alkyne–azide cycloaddition (CuAAC) of azide derivatives with terminal alkynes, we constructed a library of structurally related compounds. Screening experiments were performed with biotinylated proteins immobilized on streptavidin‐coated magnetic beads .…”

Section: Figurementioning

confidence: 99%

A DNA‐Encoded Library of Chemical Compounds Based on Common Scaffolding Structures Reveals the Impact of Ligand Geometry on Protein Recognition

et al. 2018

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A DNA-encoded chemical library (DECL) with 1.2 million compounds was synthesized by combinatorial reaction of seven central scaffolds with two sets of 343×492 building blocks. Library screening by affinity capture revealed that for some target proteins, the chemical nature of building blocks dominated the selection results, whereas for other proteins, the central scaffold also crucially contributed to ligand affinity. Molecules based on a 3,5-bis(aminomethyl)benzoic acid core structure were found to bind human serum albumin with a K value of 6 nm, while compounds with the same substituents on an equidistant but flexible l-lysine scaffold showed 140-fold lower affinity. A 18 nm tankyrase-1 binder featured l-lysine as linking moiety, while molecules based on d-Lysine or (2S,4S)-amino-l-proline showed no detectable binding to the target. This work suggests that central scaffolds which predispose the orientation of chemical building blocks toward the protein target may enhance the screening productivity of encoded libraries.

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Section: Figurementioning

confidence: 99%

A DNA‐Encoded Library of Chemical Compounds Based on Common Scaffolding Structures Reveals the Impact of Ligand Geometry on Protein Recognition

et al. 2018

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“…The click polymerization, developed based on the click reaction and having the advantages of high efficiency, mild reaction conditions, excellent selectivity, environmental friendliness, atom economy, and so on, , has become a powerful tool for the synthesis of functional polymers. Among the established click polymerizations, the alkyne-based ones have drawn much attention, which could readily furnish linear and topological polymers with advanced properties and diverse applications. − …”

Section: Introductionmentioning

confidence: 99%

Ethynylsulfone-Based Spontaneous Amino-yne Click Polymerization: A Facile Tool toward Regio- and Stereoregular Dynamic Polymers

Chen

et al. 2019

Macromolecules

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Development of efficient polymerizations is crucial for polymer science from which polymeric materials with versatile properties could be produced. In this work, a new and efficient spontaneous amino-yne click polymerization is successfully established by using activated diynes of bis(ethynylsulfone)s. Compared with the ester-activated diynes, that is, dipropiolates, bis(ethynylsulfone)s could polymerize with all kinds of diamines including aliphatic and aromatic primary and secondary ones under very mild reaction conditions, and soluble and thermally stable poly(β-aminovinylsulfone)s (PAVSs) with high weightaverage molecular weights (M w up to 160,000) and excellent regio-and stereoregularity (the ratio of E isomers up to 100%) were obtained in high yields (up to 99%). Due to the strong electron-withdrawing ability of sulfonyl groups, the resultant PAVSs show a dynamic property and could undergo the amine exchange, which makes the polymers readily degrade upon addition of monoamines. Moreover, this highly efficient spontaneous amino-yne click reaction could be used to facilely label and decorate proteins. Thus, this work not only establishes a more efficient amino-yne click polymerization, which could be used to label bioconjugates, but also provides a novel strategy to construct regio-and stereoregular dynamic polymers.

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“…The development of new effective and selective polymerizations for the synthesis of polymers with well-defined structures and unique properties is an important topic in the field of polymer science. , Generally, new polymerization could be developed on the basis of organic reaction with remarkable features of high efficiency, moderate reaction conditions, readily available reactants, and effective catalysts . Since it was introduced by Sharpless and co-workers in 2001, click chemistry has inspired a lot of scientists in diverse areas. − Click reactions are a group of nearly prefect reactions which enjoy numerous excellent features, such as high efficiency, atom economy, selectivity, great functionality tolerance, simple reaction conditions, and simple product isolation . Thanks to their great click characteristics, click reactions have drawn increasing attention of polymer chemists, and some of them have been successfully developed into powerful polymerization techniques, i.e., click polymerizations, including azide–alkyne click polymerization (AACP), − thiol–ene/yne click polymerization, − Diels–Alder click polymerization, − and the emerging amino–yne and hydroxyl–yne click polymerizations. , …”

Section: Introductionmentioning

confidence: 99%

Structure–Property Relationship of Regioregular Polytriazoles Produced by Ligand-Controlled Regiodivergent Ru(II)-Catalyzed Azide–Alkyne Click Polymerization

et al. 2019

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Exploitation of new polymerization with selectivity is of significance to the preparation of functional polymers and the study of their structure–property relationship. In this work, we successfully developed an efficient Ru(II)-catalyzed azide–alkyne click polymerization (RuAACP), of which the regioselectivity can be switched by the ligands on the Ru(II) catalysts. With RuH2(CO)(PPh3)3 as catalyst, 1,4-regioregular polytriazoles (PTAs) with high weight-average molecular weights (M w up to 15300) and high 1,4-regioregularities (the fraction of 1,4-isomer, F 1,4 up to 100%) were produced in satisfactory yields (up to 97.6%). In contrast, Cp*Ru(PPh3)2Cl-catalyzed AACP facilely yielded (up to 98.3%) 1,5-regioregular PTAs with high M w (up to 15520) and F 1,5 (up to 100%). All the obtained PTAs exhibit good solubility and high thermal stability. The glass transition temperature (T g) of 1,4-regioregular PTA is much higher than that of its 1,5-regioregular counterpart, revealing the considerable effect of the regiostructure on their T g. Both 1,4- and 1,5-regioregular PTAs containing tetraphenylethene moieties in their backbones show aggregation-induced emission features. In addition, the impact of regiostructure on the light refractivity of the PTAs was also investigated, and 1,4-regioregular PTA possesses higher refractivity indices than 1,5-regioregular PTA.

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DNA-associated click chemistry

Cited by 27 publications

References 77 publications

A DNA‐Encoded Library of Chemical Compounds Based on Common Scaffolding Structures Reveals the Impact of Ligand Geometry on Protein Recognition

A DNA‐Encoded Library of Chemical Compounds Based on Common Scaffolding Structures Reveals the Impact of Ligand Geometry on Protein Recognition

Ethynylsulfone-Based Spontaneous Amino-yne Click Polymerization: A Facile Tool toward Regio- and Stereoregular Dynamic Polymers

Structure–Property Relationship of Regioregular Polytriazoles Produced by Ligand-Controlled Regiodivergent Ru(II)-Catalyzed Azide–Alkyne Click Polymerization

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