Peptide macrocyclisation <i>via</i> late-stage reductive amination

Bell, Hayden J.; Malins, Lara R.

doi:10.1039/d2ob00782g

Cited by 7 publications

(7 citation statements)

References 54 publications

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“…Bell & Malins recently reported lysine stapling with 2,6-pyridinedialdehyde linkers and reductive amination. 229 Furan-based side chains in peptides can undergo oxidation and ring-opening to generate aldehydes or ketones, which can subsequently be further modied, such as for macrocyclisation. Madder, Suga & co-workers developed an in vitro translation system for furylalanine, which can react with a lysine side chain to eventually form a pyrrole ring in the absence of competing nucleophiles (Scheme 9E).…”

Section: Aldehyde and Ketone Modicationmentioning

confidence: 99%

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Biocompatible strategies for peptide macrocyclisation

He,

Ghosh,

Nitsche

2024

Chem. Sci.

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Section: Aldehyde and Ketone Modicationmentioning

confidence: 99%

“…Bell & Malins recently reported lysine stapling with 2,6-pyridinedialdehyde linkers and reductive amination. 229 …”

Section: Strategies For Peptide Macrocyclisationmentioning

confidence: 99%

Biocompatible strategies for peptide macrocyclisation

He,

Ghosh,

Nitsche

2024

Chem. Sci.

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“…OH PyN 3 was prepared following the synthetic procedure of Lincoln et al, with no further modifications ,,− Scheme S1 shows the overall synthetic procedure. Modified methods are described further herein.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…Small modifications to the previously reported methods were used. − Thionyl chloride (27.2 mL, 44.4 g, 373 mmol) was added dropwise to a suspension of chelidamic acid monohydrate (25.0 g, 124 mmol) in absolute EtOH (250 mL) at 0 °C. The mixture was allowed to warm at room temperature under stirring (15 min) and then heated at 80 °C for 4h.…”

Section: Experimental Sectionmentioning

confidence: 99%

Hydrogen Peroxide Disproportionation Activity Is Sensitive to Pyridine Substitutions on Manganese Catalysts Derived from 12-Membered Tetra-Aza Macrocyclic Ligands

Freire,

Johnston,

Smith

et al. 2023

Inorg. Chem.

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The abundance of manganese in nature and versatility to access different oxidation states have made manganese complexes attractive as catalysts for oxidation reactions in both biology and industry. Macrocyclic ligands offer the advantage of substantially controlling the reactivity of the manganese center through electronic tuning and steric constraint. Inspired by the manganese catalase enzyme, a biological catalyst for the disproportionation of H 2 O 2 into water and O 2 , the work herein employs 12-membered tetra-aza macrocyclic ligands to study how the inclusion of and substitution to the pyridine ring on the macrocyclic ligand scaffold impacts the reactivity of the manganese complex as a H 2 O 2 disproportionation catalyst. Synthesis and isolation of the manganese complexes was validated by characterization using UV−vis spectroscopy, SC-XRD, and cyclic voltammetry. Potentiometric titrations were used to study the ligand basicity as well as the thermodynamic equilibrium with Mn(II). Manganese complexes were also produced in situ and characterized using electrochemistry for comparison to the isolated species. Results from these studies and H 2 O 2 reactivity showed a remarkable difference among the ligands studied, revealing instead a distinction in the reactivity regarding the number of pyridine rings within the scaffold. Moreover, electron-donating groups on the 4-position of the pyridine ring enhanced the reactivity of the manganese center for H 2 O 2 disproportionation, demonstrating a handle for control of oxidation reactions using the pyridinophane macrocycle.

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“…An Amino Acid 𝐻2𝑁 − 𝐶𝐻(𝑅) − 𝐶𝑂𝑂𝐻 However, this generalization does not encompass all amino acids; deviations include those with multiple carboxyl or amino groups, imino groups, alternative types of acid groups, and configurations where the amino group is not attached to the α-carbon (1,2). It is noteworthy that most amino acids contain at least one asymmetric carbon atom, enabling their existence in multiple optically active forms.…”

Section: Introductionmentioning

confidence: 99%

Spectrophotometric Study of Excitatory Amino Acids with Ortho-Phthalaldehyde

Baloch,

Ashraf,

Durani

et al. 2024

JHRR

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Background: Understanding the concentration of amino acids in biological samples is pivotal for numerous biochemical and clinical studies. Aspartic acid and glutamic acid, being excitatory amino acids, play crucial roles in the neurotransmission processes of the mammalian brain. Their precise quantification is essential for advancing our knowledge in neurochemistry and for the diagnosis of related disorders. Objective: This study aimed to develop a robust, accurate, and sensitive spectrophotometric method for quantifying aspartic and glutamic acids in solution, both in their native forms and when complexed with ortho-phthalaldehyde (OPA), a derivatization agent that enhances their absorbance properties. Methods: Utilizing a double-beam Hitachi 220 Spectrophotometer equipped with dual 1 cm silica cuvettes, we performed spectrophotometric analyses across a wavelength range of 165 to 1000 nm. Calibration curves for aspartic acid and glutamic acid, with and without OPA, were generated by plotting absorbance against concentration. Various solvents including methanol, ethanol, acetone, and acetonitrile were evaluated for their efficacy in dissolving the amino acids and their complexes. Linear regression analysis was employed to establish the relationship between concentration and absorbance, and the method's precision and accuracy were validated through replicate measurements at multiple concentrations. Results: The calibration curves exhibited excellent linearity for both amino acids, with and without OPA, across the tested concentration ranges. For aspartic acid, absorption maxima were observed at 201 nm (106,333.33 L mol^-1 cm^-1 molar absorptivity) and 229 nm (71,250 L mol^-1 cm^-1) for its OPA derivative. Glutamic acid showed absorption maxima at 198 nm (84,333.33 L mol^-1 cm^-1) and 216 nm (128,857.14 L mol^-1 cm^-1) for its OPA derivative. The correlation coefficients (R²) for the calibration curves ranged from 0.9954 to 0.9982, indicating a high degree of linearity and reliability of the method. Conclusion: The developed spectrophotometric method provides a reliable, precise, and sensitive approach for quantifying aspartic and glutamic acids. Its application is significant for biochemical analysis and has potential implications in clinical diagnostics, offering a promising tool for neurochemical studies.

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Peptide macrocyclisation via late-stage reductive amination

Abstract: A two-component reductive amination protocol enables the macrocyclisation of unprotected peptide diamines with functionalised pyridinedialdehyde linkers.

Cited by 7 publications

References 54 publications

Biocompatible strategies for peptide macrocyclisation

Biocompatible strategies for peptide macrocyclisation

Hydrogen Peroxide Disproportionation Activity Is Sensitive to Pyridine Substitutions on Manganese Catalysts Derived from 12-Membered Tetra-Aza Macrocyclic Ligands

Spectrophotometric Study of Excitatory Amino Acids with Ortho-Phthalaldehyde

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