Literature DB >> 32914455

Photochemical Methods for Peptide Macrocyclisation.

Laetitia Raynal1, Nicholas C Rose1, James R Donald1,2, Christopher D Spicer1,2.   

Abstract

Photochemical reactions have been the subject of renewed interest over the last two decades, leading to the development of many new, diverse and powerful chemical transformations. More recently, these developments have been expanded to enable the photochemical macrocyclisation of peptides and small proteins. These constructs benefit from increased stability, structural rigidity and biological potency over their linear counterparts, providing opportunities for improved therapeutic agents. In this review, an overview of both the established and emerging methods for photochemical peptide macrocyclisation is presented, highlighting both the limitations and opportunities for further innovation in the field.
© 2020 The Authors. Published by Wiley-VCH GmbH.

Entities:  

Keywords:  macrocyclisation; peptides; photochemistry

Mesh:

Substances:

Year:  2020        PMID: 32914455      PMCID: PMC7821122          DOI: 10.1002/chem.202003779

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  112 in total

Review 1.  The cyclization of peptides and depsipeptides.

Authors:  John S Davies
Journal:  J Pept Sci       Date:  2003-08       Impact factor: 1.905

2.  Long-Lived Charge-Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer.

Authors:  Benjamin J Shields; Bryan Kudisch; Gregory D Scholes; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2018-02-12       Impact factor: 15.419

Review 3.  Flexible or fixed: a comparative review of linear and cyclic cancer-targeting peptides.

Authors:  Áron Roxin; Gang Zheng
Journal:  Future Med Chem       Date:  2012-08       Impact factor: 3.808

Review 4.  Peptide stapling techniques based on different macrocyclisation chemistries.

Authors:  Yu Heng Lau; Peterson de Andrade; Yuteng Wu; David R Spring
Journal:  Chem Soc Rev       Date:  2014-09-08       Impact factor: 54.564

5.  Comparative α-helicity of cyclic pentapeptides in water.

Authors:  Aline D de Araujo; Huy N Hoang; W Mei Kok; Frederik Diness; Praveer Gupta; Timothy A Hill; Russell W Driver; David A Price; Spiros Liras; David P Fairlie
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-14       Impact factor: 15.336

6.  Discovery of long-wavelength photoactivatable diaryltetrazoles for bioorthogonal 1,3-dipolar cycloaddition reactions.

Authors:  Yizhong Wang; Wen J Hu; Wenjiao Song; Reyna K V Lim; Qing Lin
Journal:  Org Lett       Date:  2008-08-01       Impact factor: 6.005

7.  On the Nature of C(sp3)-C(sp2) Bond Formation in Nickel-Catalyzed Tertiary Radical Cross-Couplings: A Case Study of Ni/Photoredox Catalytic Cross-Coupling of Alkyl Radicals and Aryl Halides.

Authors:  Mingbin Yuan; Zhihui Song; Shorouk O Badir; Gary A Molander; Osvaldo Gutierrez
Journal:  J Am Chem Soc       Date:  2020-04-01       Impact factor: 15.419

8.  Single electron transfer-promoted photocyclization reactions of linked acceptor-polydonor systems: effects of chain length and type on the efficiencies of macrocyclic ring-forming photoreactions of tethered alpha-silyl ether phthalimide substrates.

Authors:  Dae Won Cho; Jung Hei Choi; Sun Wha Oh; Chunsheng Quan; Ung Chan Yoon; Runtang Wang; Shaorong Yang; Patrick S Mariano
Journal:  J Am Chem Soc       Date:  2008-01-29       Impact factor: 15.419

Review 9.  Photocatalytic Modification of Amino Acids, Peptides, and Proteins.

Authors:  Cecilia Bottecchia; Timothy Noël
Journal:  Chemistry       Date:  2018-11-05       Impact factor: 5.236

10.  Stapling of unprotected helical peptides via photo-induced intramolecular thiol-yne hydrothiolation.

Authors:  Yuan Tian; Jingxu Li; Hui Zhao; Xiangze Zeng; Dongyuan Wang; Qisong Liu; Xiaogang Niu; Xuhui Huang; Naihan Xu; Zigang Li
Journal:  Chem Sci       Date:  2016-02-05       Impact factor: 9.825

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  4 in total

1.  Divergent, C-C Bond Forming Macrocyclizations Using Modular Sulfonylhydrazone and Derived Substrates.

Authors:  Wenqing Xu; Lauren E Brown; John A Porco
Journal:  J Org Chem       Date:  2021-11-03       Impact factor: 4.354

Review 2.  Photochemical Methods for Peptide Macrocyclisation.

Authors:  Laetitia Raynal; Nicholas C Rose; James R Donald; Christopher D Spicer
Journal:  Chemistry       Date:  2020-10-27       Impact factor: 5.236

3.  Visible-light-mediated catalyst-free synthesis of unnatural α-amino acids and peptide macrocycles.

Authors:  Mengran Wang; Chao Wang; Yumei Huo; Xiaobo Dang; Hongxiang Xue; Liangyu Liu; Hongli Chai; Xiuling Xie; Zhixuan Li; Doudou Lu; Zhaoqing Xu
Journal:  Nat Commun       Date:  2021-11-25       Impact factor: 14.919

Review 4.  Umpolung strategies for the functionalization of peptides and proteins.

Authors:  Andrew M White; Isabella R Palombi; Lara R Malins
Journal:  Chem Sci       Date:  2022-02-02       Impact factor: 9.825

  4 in total

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