Macrocyclization enhances affinity of chemokine-binding peptoids.
Sign Up to like & getrecommendations! Published in 2019 at "Biopolymers"
DOI: 10.1002/bip.23244
Abstract: Peptoids that bind to protein targets can be selected from one-bead-one-compound libraries. Macrocyclization has been often used to increase conformational rigidity and binding affinity in both peptides and peptoids. Here we describe a combined strategy… read more here.
Keywords: macrocyclization; affinity; macrocyclization enhances; affinity chemokine ... See more keywords
p‐Chloropropynyl Phenylalanine, a Versatile Non‐Canonical Amino Acid for Co‐Translational Peptide Macrocyclization and Side Chain Diversification
Sign Up to like & getrecommendations! Published in 2023 at "ChemBioChem"
DOI: 10.1002/cbic.202300020
Abstract: Macrocyclization has proven to be a beneficial strategy to improve upon some of the disadvantages of peptides as therapeutics. Nevertheless, many peptide cyclization strategies are not compatible with in vitro display technologies like mRNA display. Here… read more here.
Keywords: chloropropynyl phenylalanine; macrocyclization; amino acid; peptide macrocyclization ... See more keywords
Rapid and Highly Productive Assembly of a Disulfide Bond in Solid-Phase Peptide Macrocyclization.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c00078
Abstract: Here we report a highly efficient disulfide-driven peptide macrocyclization in 15 min on a solid support using persulfate as a crucial additive in iodine-mediated oxidative cyclization. The method eliminates the side products of classical iodine-mediated… read more here.
Keywords: highly productive; productive assembly; peptide macrocyclization; assembly disulfide ... See more keywords
Biomimetic Synthesis of Chejuenolides A–C by a Cryptic Lactone-Based Macrocyclization: Stereochemical Implications in Biosynthesis
Sign Up to like & getrecommendations! Published in 2023 at "ACS Central Science"
DOI: 10.1021/acscentsci.2c01096
Abstract: A hypothetical Mannich macrocyclization in the biosynthesis of chejuenolides A–C served as the basis for the synthetic design herein. Using a lactone-based linear precursor constructed via a tactic sequence of aldol–Julia–aldol reactions on a gram… read more here.
Keywords: synthesis chejuenolides; lactone based; macrocyclization; biomimetic synthesis ... See more keywords
Rapid Arene Triazene Chemistry for Macrocyclization.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c00464
Abstract: Here, we report a novel rapid arene triazene strategy for the macrocyclization of peptides that generates an inbuilt chromophoric triazene moiety at the site of cyclization within a minute. The rapid arene triazene chemistry is… read more here.
Keywords: triazene; arene triazene; chemistry; rapid arene ... See more keywords
Pyrrolysine-Inspired in Cellulo Synthesis of an Unnatural Amino Acid for Facile Macrocyclization of Proteins
Sign Up to like & getrecommendations! Published in 2023 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.3c01291
Abstract: Macrocyclization has been touted as an effective strategy to enhance the in vivo stability and efficacy of protein therapeutics. Herein, we describe a scalable and robust system based on the endogenous biosynthesis of a noncanonical… read more here.
Keywords: amino acid; protein; macrocyclization; amino ... See more keywords
Characterization of a dual function macrocyclase enables design and use of efficient macrocyclization substrates
Sign Up to like & getrecommendations! Published in 2017 at "Nature Communications"
DOI: 10.1038/s41467-017-00862-4
Abstract: Peptide macrocycles are promising therapeutic molecules because they are protease resistant, structurally rigid, membrane permeable, and capable of modulating protein–protein interactions. Here, we report the characterization of the dual function macrocyclase-peptidase enzyme involved in the… read more here.
Keywords: function macrocyclase; peptide; dual function; macrocyclization ... See more keywords
Copper(II)-mediated C-H sulphenylation or selenylation of tryptophan enabling macrocyclization of peptides.
Sign Up to like & getrecommendations! Published in 2021 at "Chemical communications"
DOI: 10.1039/d1cc04856b
Abstract: Cu(II)-mediated C-H sulphenylation or selenylation of Trp indole by a derivative of cysteine or selenocysteine enables access to the tryptathionine unit or its selenium congener. The mechanism of these protocols, which allow macrocyclization of Trp-containing… read more here.
Keywords: mediated sulphenylation; copper mediated; macrocyclization; sulphenylation selenylation ... See more keywords
Boroxine template for macrocyclization and postfunctionalization.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d2cc04691a
Abstract: A novel synthetic strategy for large macrocyclic molecules using boroxine formation was developed. For this, the threefold intramolecular olefin metathesis of 3,5-bis(alkenyloxy)phenylboroxines with various lengths of alkenyl chains, formed by the dehydration of the corresponding… read more here.
Keywords: boroxine template; macrocyclization postfunctionalization; template; macrocyclization ... See more keywords
Double click macrocyclization with Sondheimer diyne of aza-dipyrrins for B-Free bioorthogonal imaging.
Sign Up to like & getrecommendations! Published in 2023 at "Chemical communications"
DOI: 10.1039/d2cc06461h
Abstract: Sequential azide/diyne cycloadditions proved highly effective for the macrocyclization of a bis-azido aza-dipyrrin. Macrocyclic aza-dipyrrin could be produced in 30 min at rt in water with changes in fluorescence intensity and lifetimes measurable upon reaction.… read more here.
Keywords: diyne; click macrocyclization; aza dipyrrins; macrocyclization ... See more keywords
Design and development of macrocyclization methods for compounds with potential tuberculocidal activity to decrease CYP450 liver cytochrome inhibition
Sign Up to like & getrecommendations! Published in 2017 at "Russian Journal of General Chemistry"
DOI: 10.1134/s1070363217040107
Abstract: A procedure for macrocyclization of compounds with potential tuberculocidal activity was developed in order to obtaining compounds with a lower degree of inhibition of the key CYP 3A4 cytochrome. read more here.
Keywords: tuberculocidal activity; potential tuberculocidal; compounds potential; macrocyclization ... See more keywords