Development of fructose-1,6-bisphosphate aldolase enzyme peptide mimics as biocatalysts in direct asymmetric aldol reactions

Peme, Thabo; Brady, Dean; Juma, Wanyama P.; Makatini, Maya M.

doi:10.1039/d1ra06616a

Cited by 4 publications

(2 citation statements)

References 63 publications

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“…In the presence of DMSO as a solvent, only trace amounts of the product were formed. This research highlights the potential of these peptides for enantioselective catalysis in aldol reactions [29].…”

Section: Introductionmentioning

confidence: 92%

A Simple Screening and Optimization Bioprocess for Long-Chain Peptide Catalysts Applied to Asymmetric Aldol Reaction

Wang,

Teng,

Wang

et al. 2023

Molecules

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Peptides have demonstrated their efficacy as catalysts in asymmetric aldol reactions. But the constraints inherent in chemical synthesis have imposed limitations on the viability of long-chain peptide catalysts. A noticeable dearth of tools has impeded the swift and effective screening of peptide catalysts using biological methods. To address this, we introduce a straightforward bioprocess for the screening of peptide catalysts for asymmetric aldol reactions. We synthesized several peptides through this method and obtained a 15-amino acid peptide. This peptide exhibited asymmetric aldol catalytic activity, achieving 77% ee in DMSO solvent and 63% ee with over an 80.8% yield in DMSO mixed with a pH 9.0 buffer solution. The successful application of our innovative approach not only represents an advancement but also paves the way for currently unexplored research avenues.

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Section: Introductionmentioning

confidence: 92%

A Simple Screening and Optimization Bioprocess for Long-Chain Peptide Catalysts Applied to Asymmetric Aldol Reaction

Wang,

Teng,

Wang

et al. 2023

Molecules

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“…8,9 In 2021, Makatini and coworkers reported a solid-phase peptide-promoted aldol reaction between ketones and aldehydes (Scheme 2b). 10 Addition of a small amount of water was beneficial for yield and stereoselectivity. The role of water was postulated to influence the reaction rate significantly, and stabilize the transition state as well as the ground state of the substrate through improving hydrogen bonding.…”

Section: Water-enabling Improvement Of Reactivity or Stereoselectivitymentioning

confidence: 99%

Water-enabling strategies for asymmetric catalysis

Wen,

Feng,

Lin

2024

Org. Biomol. Chem.

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Peptide-Functionalized Gold Nanoparticles as Organocatalysts for Asymmetric Aldol Reactions

Peme,

Brady,

Shumbula

et al. 2024

Catalysts

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The use of high catalyst loading is required for most of the organocatalyzed asymmetric aldol reactions in organic synthesis, and this often presents challenges during purification and difficulties in catalyst recovery from the reaction mixture. The immobilization of the catalyst onto gold nanoparticles (AuNPs) can change the structural conformations of the catalyst, thereby improving its catalytic activity and reusability. Herein we report on the synthesis of aldolase mimetic peptide coupled to gold nanoparticles (AuNPs) as efficient organocatalysts for asymmetric aldol reaction. AuNPs were synthesized using the Turkevich method. The conjugation of the peptide to AuNPs was characterized using surface plasmon resonance (SPR), Raman and X-ray photoelectron spectroscopy, and transmission electron microscopy (TEM) was used for particle size determination. The produced nanoparticles, whose sizes depended on the reduction method, were quasi-spherical with a relatively narrow size distribution. The peptide–AuNP conjugates were evaluated for aldol reaction catalytic activity between carbonyls p-nitrobenzaldehyde and cyclohexanone. The products were obtained with good yields (up to 85%) and enantioselectivity (up to 94%). The influence of organic solvents, pH and buffer solutions was also investigated. The results showed that the buffer solutions regulated the colloidal stability of AuNPs, resulting in a significant enhancement in the catalytic rate of the peptide–AuNP conjugate.

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Development of fructose-1,6-bisphosphate aldolase enzyme peptide mimics as biocatalysts in direct asymmetric aldol reactions

Abstract: Novel asymmetric aldol reaction catalysing fructose-1,6-bisphosphate aldolase peptide mimics with secondary structural motifs.

Cited by 4 publications

References 63 publications

A Simple Screening and Optimization Bioprocess for Long-Chain Peptide Catalysts Applied to Asymmetric Aldol Reaction

A Simple Screening and Optimization Bioprocess for Long-Chain Peptide Catalysts Applied to Asymmetric Aldol Reaction

Water-enabling strategies for asymmetric catalysis

Peptide-Functionalized Gold Nanoparticles as Organocatalysts for Asymmetric Aldol Reactions

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