Diverse backbone-cyclized peptides via codon reprogramming.

Nature Chemical Biology
Takashi KawakamiHiroaki Suga

Abstract

We report a methodology for the ribosomal synthesis of backbone-cyclized peptides involving genetic code reprogramming to introduce one or more nonproteinogenic amino acids. Expression of linear peptides bearing a cysteine-proline dipeptide sequence followed by glycolic acid results in self-rearrangement to a C-terminal diketopiperadine-thioester, which non-enzymatically generates a cyclized peptide. We demonstrate the ribosomal synthesis of several naturally occurring backbone-cyclized peptides and a library based on a bicyclic scaffold, and we identify bioactive sequences by screening and deconvolution.

References

Oct 1, 1995·Trends in Biotechnology·R C Ladner
Aug 15, 1997·Science·R W KingM W Kirschner
Nov 14, 1997·Proceedings of the National Academy of Sciences of the United States of America·R W Roberts, J W Szostak
Nov 26, 1999·Proceedings of the National Academy of Sciences of the United States of America·C P ScottS J Benkovic
Aug 2, 2001·Nature Biotechnology·Y ShimizuT Ueda
Mar 15, 2002·Trends in Biochemical Sciences·Manuela Trabi, David J Craik
Mar 5, 2003·Chemical Communications : Chem Comm·Rahul M Kohli, Christopher T Walsh
May 20, 2003·Proceedings of the National Academy of Sciences of the United States of America·Anthony C ForsterStephen C Blacklow
Nov 17, 2004·Current Protein & Peptide Science·Michael L J KorsinczkyDavid J Craik
Dec 29, 2005·Angewandte Chemie·Richard H KimuraJulio A Camarero
Apr 22, 2006·Nature Methods·Hiroshi MurakamiHiroaki Suga
Jun 23, 2006·The Journal of Biological Chemistry·Wei WangRobert I Lehrer
Nov 7, 2006·Nature Chemical Biology·Mohamed S DoniaEric W Schmidt
Sep 13, 2007·International Journal of Biological Sciences·Shingo UenoYuzuru Husimi
Sep 22, 2007·Current Opinion in Chemical Biology·Masaki OhuchiHiroaki Suga
Dec 22, 2007·Chemistry & Biology·Atsushi OhtaHiroaki Suga
Feb 6, 2008·Current Opinion in Chemical Biology·Atsushi OhtaHiroaki Suga
Dec 5, 2008·Journal of the American Chemical Society·Takashi KawakamiHiroaki Suga

❮ Previous
Next ❯

Citations

Jun 30, 2011·Accounts of Chemical Research·Jumpei MorimotoHiroaki Suga
Jun 4, 2011·Nature Protocols·Yuki GotoHiroaki Suga
Oct 5, 2010·Chemical Communications : Chem Comm·Ji Hoon LeeHyun-Suk Lim
Jul 19, 2011·Chemical Communications : Chem Comm·Takayuki KatohHiroaki Suga
Feb 14, 2012·Molecular BioSystems·Andrew GouldJulio A Camarero
Sep 18, 2013·Proceedings of the National Academy of Sciences of the United States of America·Kenneth V LawsonPatrick G Harran
Jun 19, 2012·The Journal of Biological Chemistry·Teshome L Aboye, Julio A Camarero
Sep 21, 2011·Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences·Hiroaki SugaNaohiro Terasaka
Mar 4, 2014·Annual Review of Biochemistry·Toby PassiouraHiroaki Suga
Feb 6, 2014·Applied Microbiology and Biotechnology·Darko BalkeSabine Müller
Jun 9, 2014·Nature Chemical Biology·Naohiro TerasakaHiroaki Suga
Mar 25, 2015·International Journal of Molecular Sciences·Naohiro TerasakaHiroaki Suga
Mar 20, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kenichiro ItoHiroaki Suga
Apr 10, 2012·Current Opinion in Biotechnology·D Calvin Harris, Michael C Jewett
Mar 10, 2012·Current Opinion in Chemical Biology·Christopher J Hipolito, Hiroaki Suga
Sep 29, 2011·Metabolic Engineering·C Eric Hodgman, Michael C Jewett
Oct 26, 2012·Journal of Nucleic Acids·Takashi Kawakami, Hiroshi Murakami
Apr 1, 2014·Current Opinion in Structural Biology·Christopher J HipolitoHiroaki Suga
Aug 19, 2014·Trends in Biochemical Sciences·Toby Passioura, Hiroaki Suga
Jan 17, 2015·European Journal of Medicinal Chemistry·Natia Tsomaia
Nov 7, 2014·The Journal of Physical Chemistry. B·Anne C ConibearDavid J Craik
Jan 17, 2017·Chemical Communications : Chem Comm·Toby Passioura, Hiroaki Suga
Dec 3, 2016·Nihon yakurigaku zasshi. Folia pharmacologica Japonica·Keiichi Masuya
Apr 10, 2016·Angewandte Chemie·Emilia OueisJames H Naismith
Jul 12, 2016·Angewandte Chemie·Emilia OueisJames H Naismith
Feb 22, 2012·Israel Journal of Chemistry·Derek MacmillanBhavesh Premdjee
Dec 4, 2012·Chembiochem : a European Journal of Chemical Biology·John R FrostRudi Fasan
Jul 22, 2014·Chemistry : a European Journal·Katherine R Lennard, Ali Tavassoli
Aug 1, 2014·Angewandte Chemie·Anne C Conibear, David J Craik
Jan 16, 2014·The Journal of Biological Chemistry·Xinying JiaDavid J Craik
Sep 15, 2018·Chembiochem : a European Journal of Chemical Biology·Shubhendu PaleiHenning D Mootz
Apr 20, 2010·Organic & Biomolecular Chemistry·Jaskiranjit Kang, Derek Macmillan
Jun 22, 2010·Biopolymers·Yossef Kliger
Mar 24, 2020·Nature Chemical Biology·Satoshi IshidaHiroaki Suga
Jan 15, 2015·Journal of Biomolecular Screening·Andrew D FosterAli Tavassoli
Mar 23, 2013·Chemistry : a European Journal·Toby Passioura, Hiroaki Suga

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.