Development of the Juliá−Colonna Asymmetric Epoxidation Reaction:  Part 1. Preparation and Activation of the Polyleucine Catalyst

Baars, Sylvia M.; Drauz, Karlheinz; Krimmer, Hans‐Peter; Roberts, Stanley M.; Sander, Julia; Skidmore, John; Zanardi, G.

doi:10.1021/op0300037

Cited by 44 publications

(15 citation statements)

References 22 publications

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“…Based on literature precedent, catalysts generally categorized into phase transfer catalyst, metal/transition metals and enzyme and protein based catalyst ( Fig. 1) [88][89][90][91][92][93][94][95][96][97][98].…”

Section: Type Of Catalystsmentioning

confidence: 99%

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Farooq

Ngaini

2020

Chemistry Africa

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Epoxy chalcone is a heterocyclic molecule and an important precursor for the synthesis of biologically active compounds. This mini-review is elucidating the synthetic strategies of chalcone epoxide via one pot and two pot routes including nature of reactants, nature of catalyst and variety of catalyst to improve yield of desired product, biological applications and advantages and drawbacks of these synthetic strategies. One pot route has wide variety of reactants and efficient one is the condensation of aldehyde and ketone. However, two pot route is consisted of chalcone synthesis preceding to epoxy chalcone. The synthetic routes for the preparation of epoxy chalcone and the usage as a precursor for the synthesis of various organic molecules with biological application is comprehensively discussed. This review is outstanding in organic chemistry and pharmaceutical industries to produce new molecules with various applications. Graphic AbstractO O

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Section: Type Of Catalystsmentioning

confidence: 99%

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Farooq

Ngaini

2020

Chemistry Africa

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“…Such an immobilization strategy is certainly one of the simplest approaches for obtaining a recyclable material since the procedure is based on mixing unmodifi ed amorphous silica gel and pLL followed by fi ltration. An improved protocol for the preparation and activation of the pLL catalyst for subsequent immobilization on silica gel was later reported [14] . Epoxidation with silica -adsorbed pLL was successfully employed in the synthesis of the nonsteroidal anti -infl ammatory agent ( S ) -Fenoprofen [13] .…”

Section: Noncovalently Linked: Silicamentioning

confidence: 99%

Recyclable Organocatalysts in Asymmetric Reactions

Gruttadauria

Giacalone

Noto

2011

Catalytic Methods in Asymmetric Synthesis

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“…Synthetic polypeptides, commonly prepared by the ring-opening polymerization (ROP) of amino acid N -carboxyanhydrides (NCA), are a family of biomimetic materials that can be applied as catalysts for heterogeneous reactions, self-assembling building blocks, surfactants for double emulsion, drugs carriers, tissue engineering scaffolds, antimicrobial agents, and alternatives to polyethylene glycol (PEG) 1 – 15 . For example, poly- l -alanine and poly- l -leucine are established industrial catalysts for asymmetric Juliá–Colonna epoxidation reactions 16 . Copaxone ® , a random co-polypeptide prepared through the ROP of four different NCAs, is a blockbuster drug for multiple sclerosis which generated an annual global sales of 4 billion USD in 2012 17 , 18 .…”

Section: Introductionmentioning

confidence: 99%

A moisture-tolerant route to unprotected α/β-amino acid N-carboxyanhydrides and facile synthesis of hyperbranched polypeptides

et al. 2021

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A great hurdle in the production of synthetic polypeptides lies in the access of N-carboxyanhydrides (NCA) monomers, which requires dry solvents, Schlenk line/gloveboxe, and protection of side-chain functional groups. Here we report a robust method for preparing unprotected NCA monomers in air and under moisture. The method employs epoxy compounds as ultra-fast scavengers of hydrogen chloride to allow assisted ring-closure and prevent NCA from acid-catalyzed decomposition under moist conditions. The broad scope and functional group tolerance of the method are demonstrated by the facile synthesis of over 30 different α/β-amino acid NCAs, including many otherwise inaccessible compounds with reactive functional groups, at high yield, high purity, and up to decagram scales. The utility of the method and the unprotected NCAs is demonstrated by the facile synthesis of two water-soluble polypeptides that are promising candidates for drug delivery and protein modification. Overall, our strategy holds great potential for facilitating the synthesis of NCA and expanding the industrial application of synthetic polypeptides.

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Development of the Juliá−Colonna Asymmetric Epoxidation Reaction: Part 1. Preparation and Activation of the Polyleucine Catalyst

Abstract: The preparation of silica-supported poly-L-leucine has been studied under a variety of reaction conditions leading to an efficient procedure for the preparation of material suitable for use in the Julia ´-Colonna asymmetric epoxidation reaction.

Cited by 44 publications

References 22 publications

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Recyclable Organocatalysts in Asymmetric Reactions

A moisture-tolerant route to unprotected α/β-amino acid N-carboxyanhydrides and facile synthesis of hyperbranched polypeptides

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