Polypeptoids synthesis based on Ugi reaction: Advances and perspectives

Tao, Yue; Wang, Zhen; Tao, Youhua

doi:10.1002/bip.23288

Cited by 22 publications

(28 citation statements)

References 85 publications

(100 reference statements)

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“…Ugi reaction is a four-component reaction, and the reactants are commonly acid, amine, isocyanide, and aldehyde [ 57 , 58 ]. This reaction has gained great attention and been utilized in the fields of combinatorial chemistry, pharmaceutics, and life science due to its mild reaction conditions, high efficiency, functional group tolerance, and atom economy [ 59 , 60 ]. Recently, Meier demonstrated a very efficient and modular approach to synthesizing diversely substituted polyamides via the Ugi four-component reaction [ 45 ].…”

Section: Synthetic Strategies Of Oegylated Poly(amino Acid)smentioning

confidence: 99%

Recent Advances in Thermoresponsive OEGylated Poly(amino acid)s

Geng

Wang

2021

Polymers

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Thermoresponsive polymers have been widely studied in the past decades due to their potential applications in biomedicine, nanotechnology, and so on. As is known, poly(N-isopropylacrylamide) (PNIPAM) and poly(oligo(ethylene glycol)methacrylates) (POEGMAs) are the most popular thermoresponsive polymers, and have been studied extensively. However, more advanced thermoresponsive polymers with excellent biocompatibility, biodegradability, and bioactivity also need to be developed for biomedical applications. OEGylated poly(amino acid)s are a kind of novel polymer which are synthesized by attaching one or multiple oligo(ethylene glycol) (OEG) chains to poly(amino acid) (PAA).These polymers combine the great solubility of OEG, and the excellent biocompatibility, biodegradability and well defined secondary structures of PAA. These advantages allow them to have great application prospects in the field of biomedicine. Therefore, the study of OEGylated poly(amino acid)s has attracted more attention recently. In this review, we summarized the development of thermoresponsive OEGylated poly(amino acid)s in recent years, including the synthesis method (such as ring-opening polymerization, post-polymerization modification, and Ugi reaction), stimuli-response behavior study, and secondary structure study. We hope that this periodical summary will be more conducive to design, synthesis and application of OEGylated poly(amino acid)s in the future.

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Section: Synthetic Strategies Of Oegylated Poly(amino Acid)smentioning

confidence: 99%

Recent Advances in Thermoresponsive OEGylated Poly(amino acid)s

Geng

Wang

2021

Polymers

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“…The C�N in 102 is attacked by the À COO À to give 103, and the rearrangement of acyl group (deriving from 99) to the nitrogen atom (originally providing by 97) accesses to the dipeptide chain of 104. [39] Both the Ugi 4CR and Passerini 3CR are capable of integrating antioxidative moieties into an aliphatic chain and act as strategies for constructing aliphatic antioxidants. The equation (18) in Figure 7 outlines such an example that 3,4di-tert-butoxylcarbonylbenzaldehyde (106, À OHs in 41 are protected by tert-butoxylcarbonyl group) participates in the Ugi 4CR with 4-methoxybenzylamine (105), glycine (107, -NH 2 is protected by carbobenzyloxyl group), and cyclohexyl isocyanide (86) to afford a dipeptide chain in 108.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

“…The C=N + in the imine ( 100 ) performs nucleophilic addition with the carbanion in methyl isocyanoacetate ( 101 ) to afford an intermediate ( 102 , whose structure is similar to 94 in the Passerini 3CR). The C≡N in 102 is attacked by the −COO − to give 103 , and the rearrangement of acyl group (deriving from 99 ) to the nitrogen atom (originally providing by 97 ) accesses to the dipeptide chain of 104 [39] . Both the Ugi 4CR and Passerini 3CR are capable of integrating antioxidative moieties into an aliphatic chain and act as strategies for constructing aliphatic antioxidants.…”

Section: Ugi and Passerini Reactionsmentioning

confidence: 99%

Multicomponent Reactions for Integrating Multiple Functional Groups into an Antioxidant

Liu

2020

The Chemical Record

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A large number of convincing evidences has revealed the correlation of the pathogeny of diseases with the oxidative damages of DNA, protein, biomembrane, and other biological species, while supplementation of antioxidants is demonstrated to be a promising way to avoid, at least, rectify the unbalance redox status in vivo. Although many endeavors have focused on synthesis of antioxidants, a main hurdle still hinders the wide usages of synthetic antioxidants because of low bioavailability and potential cytotoxicity. The search for antioxidants with multiple functional groups being recognized by different receptors becomes a much sought by researchers, and multicomponent reactions (MCRs) provide with powerful tools for the construction of multifunctional antioxidants. Presented herein is a personal account on the application of MCRs for the synthesis of multifunctional antioxidants, while radical-induced oxidation of DNA acts as the experimental system for evaluating antioxidative effect. Concretely, the Biginelli three-component reaction (3CR) affords such a dihydropyrimidine scaffold that the tautomerization between C=S and CÀ SH leads to antioxidative effect. The Povarov 3CR is able to integrate multiple antioxidative groups, i. e., ferrocenyl and À N(CH 3) 2 , into a quinoline scaffold, while the Groebke 3CR provides with imidazo[1,2-a]pyridine skeleton for inhibiting DNA oxidation. Additionally, the Knoevenagel-related MCRs also become efficient strategies for achieving radical-scavengers. On the other hand, the Ugi 4CR and Passerini 3CR result in the dipeptide and α-acyloxycarboxamide, respectively, with the benefit for the integration of antioxidative features by aliphatic chains. Therefore, MCRs have emerged as efficient tools for integrating multiple antioxidative features into one molecule in order to meet with complicated requirements from various biological surroundings.

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“…Among the few reviews dedicated to this topic, Tao et al documented polypeptoids preparation based on Ugi reaction of amino acids in 2019. [ 27 ] As a result, this mini review is not meant to offer a comprehensive review of the research activities in the field. It will focus on the recent development in the synthetic approaches to access sequence‐defined polypeptoids and highlight the usage of bio‐based furfural in the Ugi polymerization that is pertinent to the future development of polypeptoids from sustainable aldehyde ( Figure ).…”

Section: Introductionmentioning

confidence: 99%

Ugi Reaction of Amino Acids: From Facile Synthesis of Polypeptoids to Sequence‐Defined Macromolecules

Tao

2020

Macromol. Rapid Commun.

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Polypeptoids have been prepared and researched for more than 20 years. However, the efficient generation of polypeptoids and sequence‐defined polypeptoids faces many challenges and difficulties. The Ugi reaction of amino acids has recently been introduced into polypeptoid chemistry as a new and powerful method to furnish polypeptoids. In the following mini review, the recent progress on the application of the Ugi reaction of amino acids in polypeptoid science, including polypeptoid from sustainable furfural, sequence‐defined polypeptoids, and more is summarized. Moreover, the future development of the Ugi reaction of amino acids in polypeptoid science is discussed.

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Polypeptoids synthesis based on Ugi reaction: Advances and perspectives

Cited by 22 publications

References 85 publications

Recent Advances in Thermoresponsive OEGylated Poly(amino acid)s

Recent Advances in Thermoresponsive OEGylated Poly(amino acid)s

Multicomponent Reactions for Integrating Multiple Functional Groups into an Antioxidant

Ugi Reaction of Amino Acids: From Facile Synthesis of Polypeptoids to Sequence‐Defined Macromolecules

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