Synthesis of Ribosomally Synthesized and Post-Translationally Modified Peptides Containing C–C Cross-Links

Laws, David; Plouch, Eleda V.; Blakey, Simon B.

doi:10.1021/acs.jnatprod.2c00508

Cited by 7 publications

(7 citation statements)

References 62 publications

(158 reference statements)

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“…Carbon–carbon bond (C–C bond) forming is a valuable topic in organic chemistry, pharmacy, and materials science due to the essential role of C–C bonds to be the bridge for organic building block connection. − For the sake of sustainable development, atomic economical and environmentally friendly methods for C–C bond formation are sought after in both academia and industry. − With the benefits of avoiding waste generation, C–C bond formation processes based on borrowing hydrogen or hydrogen autotransfer ((BH/HA) strategies have attracted much attention in recent years (Scheme a). − …”

Section: Introductionmentioning

confidence: 99%

Surmounting Alkoxide Trap Strategy: N-Heterocyclic Carbene Chromium(0)-Catalyzed C-Alkylation between Alcohols

Su,

Chen,

et al. 2023

ACS Catal.

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The crucial role of the alkoxide trap problem and the impact of the oxidation state of the chromium center were demonstrated on the catalytic activity due to the d-wall issue. Through the strategy of surmounting the alkoxide trap, a Cr(0) catalyst was presented herein for efficient C-alkylation between alcohols via borrowing hydrogen/hydrogen autotransfer. The synthesized bis-(N-heterocyclic carbene)-Cr(0) system shows an efficient catalytic performance (40 examples, up to 96% yield). Only a catalytic loading of a cheap and readily available base NaOH is effective enough for the reaction. Compared with Cr(III)/Cr(II), Cr(0) can well avoid the d-p π interaction in the key metal-alkoxide intermediate, thus overcoming the thermodynamic sink due to the alkoxide trap problem. It is plausible that the Cr(III) systems need to be reduced to Cr(II) for weakening the alkoxide trap effect and enhancing activity by using reductive strong bases. This surmounting alkoxide trap strategy should be helpful for the development of efficient and nonprecious transition metal catalysts.

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Section: Introductionmentioning

confidence: 99%

Surmounting Alkoxide Trap Strategy: N-Heterocyclic Carbene Chromium(0)-Catalyzed C-Alkylation between Alcohols

Su,

Chen,

et al. 2023

ACS Catal.

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“…Cyclophanes derived from nature and synthetic chemistry have intrigued chemists for the last 70 years. [1][2][3][4][5][6][7] The name cyclophane was originally designated for compounds containing two benzene rings, such as [2,2]-paracyclophane. This description was further expanded to rings containing a single aromatic ring, such as [n]-meta-or [n]-paracyclophane.…”

Section: Introductionmentioning

confidence: 99%

Bacterial cyclophane-containing RiPPs from radical SAM enzymes

Phan,

Morinaka

2024

Nat. Prod. Rep.

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“…The underdeveloped reactivity of its phenolic side chain presents a novel platform to develop Tyr-selective peptide cyclization methods. Considering the need for such strategies, we drew inspiration from the simplicity of other oxidation-induced cyclizations that occur spontaneously under aerobic conditions for peptides containing multiple cysteine (Cys) residues, such as the facile conversion of 4 into vasopressin 5 , and enzymatically, such as the remarkable conversion of 6 into C–C bond-linked cyclic peptide 7 . − Given the prevalence of Tyr-linked cyclic peptide natural products, we set out to develop a method for the oxidatively induced cyclization of Tyr-containing peptides.…”

Section: Introductionmentioning

confidence: 99%

Chemoselective, Oxidation-Induced Macrocyclization of Tyrosine-Containing Peptides

et al. 2023

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Inspired by nature’s wide range of oxidation-induced modifications to install cross-links and cycles at tyrosine (Tyr) and other phenol-containing residue side chains, we report a Tyr-selective strategy for the preparation of Tyr-linked cyclic peptides. This approach leverages N4-substituted 1,2,4-triazoline-3,5-diones (TADs) as azo electrophiles that react chemoselectively with the phenolic side chain of Tyr residues to form stable C–N1-linked cyclic peptides. In the developed method, a precursor 1,2,4-triazolidine-3,5-dione moiety, also known as urazole, is readily constructed at any free amine revealed on a solid-supported peptide. Once prepared, the N4-substituted urazole peptide is selectively oxidized using mild, peptide-compatible conditions to generate an electrophilic N4-substituted TAD peptide intermediate that reacts selectively under aqueous conditions with internal and terminal Tyr residues to furnish Tyr-linked cyclic peptides. The approach demonstrates good tolerance of native residue side chains and enables access to cyclic peptides ranging from 3- to 11-residues in size (16- to 38-atom-containing cycles). The identity of the installed Tyr-linkage, a stable covalent C–N1 bond, was characterized using NMR spectroscopy. Finally, we applied the developed method to prepare biologically active Tyr-linked cyclic peptides bearing the integrin-binding RGDf epitope.

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Synthesis of Ribosomally Synthesized and Post-Translationally Modified Peptides Containing C–C Cross-Links

Cited by 7 publications

References 62 publications

Surmounting Alkoxide Trap Strategy: N-Heterocyclic Carbene Chromium(0)-Catalyzed C-Alkylation between Alcohols

Surmounting Alkoxide Trap Strategy: N-Heterocyclic Carbene Chromium(0)-Catalyzed C-Alkylation between Alcohols

Bacterial cyclophane-containing RiPPs from radical SAM enzymes

Chemoselective, Oxidation-Induced Macrocyclization of Tyrosine-Containing Peptides

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