Petasis-Ugi ligands: New affinity tools for the enrichment of phosphorylated peptides

Batalha, Íris L.; Roque, Ana C. A.

doi:10.1016/j.jchromb.2016.07.035

Cited by 9 publications

(16 citation statements)

References 31 publications

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“…Furthermore, to expand the repertoire of novel affinity ligands, one-pot two-step Petasis-Ugi reaction was designed by Batalha and Roque . The Petasis reaction, also referred to the boronic acid Mannich reaction, is a MCR that enables the preparation of amines and their derivatives such as α-amino acids which discovered by Nicos Petasis in 1993 .…”

Section: Covalent Functionalization Through Multicomponent Reactionsmentioning

confidence: 99%

“…107 (Scheme 25) Furthermore, to expand the repertoire of novel affinity ligands, one-pot two-step Petasis-Ugi reaction was designed by Batalha and Roque. 108 The Petasis reaction, also referred to the boronic acid Mannich reaction, is a MCR that enables the preparation of amines and their derivatives such as α-amino acids which discovered by Nicos Petasis in 1993. 109 The reaction proceeds via an imine with the organic ligand of the boronic acid 78 acting as the nucleophile, similar to the role of the enolizable ketone component in the original Mannich reaction.…”

Section: Acs Combinatorial Sciencementioning

confidence: 99%

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Materials Functionalization with Multicomponent Reactions: State of the Art

Afshari

Shaabani

2018

ACS Comb. Sci.

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The emergence of neoteric synthetic routes for materials functionalization is an interesting phenomenon in materials chemistry. In particular, the union of materials chemistry with multicomponent reactions (MCRs) opens a new avenue leading to the realm of highly innovative functionalized architectures with unique features. MCRs have recently been recognized as considerable part of the synthetic chemist's toolbox due to their great efficiency, inherent molecular diversity, atom and pot economy along with operational simplicity. Also, MCRs can improve E-factor and mass intensity as important green chemistry metrics. By rational tuning of the materials, as well as the MCRs, wide ranges of functionalized materials can be produced with tailorable properties that can play important roles in the plethora of applications. To date, there has not reported any exclusive review of a materials functionalization with MCRs. This critical review highlights the state-of-the-art on the one-pot functionalization of carbonaceous and siliceous materials, polysaccharides, proteins, enzymes, synthetic polymers, etc., via diverse kind of MCRs like Ugi, Passerini, Petasis, Khabachnik-Fields, Biginelli, and MALI reactions through covalent or noncovalent manners. Besides the complementary discussion of synthetic routes, superior properties and detailed applicability of each functionalized material in modern technologies are discussed. Our outlook also emphasizes future strategies for this unprecedented area and their use as materials for industrial implementation. With no doubt, MCRs-functionalization of materials bridges the gap between materials science domain and applied chemistry.

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Section: Covalent Functionalization Through Multicomponent Reactionsmentioning

confidence: 99%

Section: Acs Combinatorial Sciencementioning

confidence: 99%

Materials Functionalization with Multicomponent Reactions: State of the Art

Afshari

Shaabani

2018

ACS Comb. Sci.

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“…An applied first filtration rule is that examples are only being grouped into the second section of “three-component Petasis reactions” if they cannot be appropriately covered under other sections. It is noteworthy that PRs have been successfully demonstrated in the solid phase for the synthesis of both amino acids and peptides, − including the synthesis of fluorous-tagged N -alkylated amino acids using fluorous-tagged hydroxylamines, , derivatization and stapling of peptides by an on-resin PR, and combinatorial synthesis of peptidomimetics employing PR-Ugi sequence reactions, but such solid-supported PRs are generally not covered in this Review.…”

Section: Introductionmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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The Petasis boron–Mannich reaction, simply referred to as the Petasis reaction, is a powerful multicomponent coupling reaction of a boronic acid, an amine, and a carbonyl derivative. Highly functionalized amines with multiple stereogenic centers can be efficiently accessed via the Petasis reaction with high levels of both diastereoselectivity and enantioselectivity. By drawing attention to examples reported in the past 8 years, this Review demonstrates the breadth of the reactivity and synthetic applications of Petasis reactions in several frontiers: the expansion of the substrate scope in the classic three-component process; nonclassic Petasis reactions with additional components; Petasis-type reactions with noncanonical substrates, mechanism, and products; new asymmetric versions assisted by chiral catalysts; combinations with a secondary or tertiary transformation in a cascade- or sequence-specific manner to access structurally complex, natural-product-like heterocycles; and the synthesis of polyhydroxy alkaloids and biologically interesting molecules.

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“…C-C and C-N bond-forming U-4CR can constitute a scaffold providing enormous molecular diversity. U-4CR protocol has been utilized in various fields of chemistry including separation science where it has been employed mainly in affinity chromatography [26][27][28][29][30][31][32][33][34][35][36][37][38][39]. Surprisingly, up to the present time, its adoption in other chromatographic modes has been rather scarce.…”

Section: Introductionmentioning

confidence: 99%

New multimodal stationary phases prepared by Ugi multicomponent approach

Sýkora

Záruba

Butnariu

et al. 2020

J of Separation Science

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Eight different stationary phases based on two aminopropyl silicas of different brands suitable for multimodal chromatography applications have been prepared by a four-component Ugi reaction. The intention was to synthesize stationary phases significantly differing in their properties hereby demonstrating flexibility of the Ugi synthetic protocol. Diverse functional groups including a nonpolar long aliphatic chain, phenyl moiety, cholic acid scaffold, phenylboronic and monosaccharide units, charged betaine, and arginine moieties were immobilized on a silica surface. The novel sorbents were extensively characterized by elemental analysis, Raman spectroscopy, and chromatography. Considering the anchored chemical structures covalently bonded to the silica surface, reversed-phase, hydrophilic, and ion-exchange separation modes were expected. The chromatographic evaluation was performed directed to map the potential of the individual columns specifically in the mentioned chromatographic modes. The Ugi synthetic protocol has proven to be a simple, feasible, and versatile tool for the synthesis of sorbents of variable properties. The newly prepared stationary phases differed considerably in hydrophobicity and ion-exchange ability. A significant influence of the supporting aminopropyl silica on the final chromatographic behavior was observed. Finally, one practical example confirming applicability of the newly prepared sorbents was demonstrated in separation of cytarabine.

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Petasis-Ugi ligands: New affinity tools for the enrichment of phosphorylated peptides

Cited by 9 publications

References 31 publications

Materials Functionalization with Multicomponent Reactions: State of the Art

Materials Functionalization with Multicomponent Reactions: State of the Art

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

New multimodal stationary phases prepared by Ugi multicomponent approach

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