Literature DB >> 19246005

Photocleavage of the polypeptide backbone by 2-nitrophenylalanine.

Francis B Peters1, Ansgar Brock, Jiangyun Wang, Peter G Schultz.   

Abstract

Photocleavage of the polypeptide backbone is potentially a powerful and general method to activate or deactivate functional peptides and proteins with high spatial and temporal resolution. Here we show that 2-nitrophenylalanine is able to photochemically cleave the polypeptide backbone by an unusual cinnoline-forming reaction. This unnatural amino acid was genetically encoded in E. coli, and protein containing 2-nitrophenylalanine was expressed and site-specifically photocleaved.

Entities:  

Mesh:

Substances:

Year:  2009        PMID: 19246005      PMCID: PMC2714363          DOI: 10.1016/j.chembiol.2009.01.013

Source DB:  PubMed          Journal:  Chem Biol        ISSN: 1074-5521


  14 in total

1.  Photoremovable protecting groups: reaction mechanisms and applications.

Authors:  Anna Paola Pelliccioli; Jakob Wirz
Journal:  Photochem Photobiol Sci       Date:  2002-07       Impact factor: 3.982

2.  Design and synthesis of photochemically controllable caspase-3.

Authors:  Masayuki Endo; Koji Nakayama; Yuka Kaida; Tetsuro Majima
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-25       Impact factor: 15.336

3.  A ligation and photorelease strategy for the temporal and spatial control of protein function in living cells.

Authors:  Jean-Philippe Pellois; Tom W Muir
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-05       Impact factor: 15.336

Review 4.  Photochemical control of biological processes.

Authors:  Douglas D Young; Alexander Deiters
Journal:  Org Biomol Chem       Date:  2006-12-20       Impact factor: 3.876

5.  The nitrodibenzofuran chromophore: a new caging group for ultra-efficient photolysis in living cells.

Authors:  Atsuya Momotake; Nicolas Lindegger; Ernst Niggli; Robert J Barsotti; Graham C R Ellis-Davies
Journal:  Nat Methods       Date:  2006-01       Impact factor: 28.547

6.  Expanding the genetic code of Escherichia coli.

Authors:  L Wang; A Brock; B Herberich; P G Schultz
Journal:  Science       Date:  2001-04-20       Impact factor: 47.728

7.  Site-specific, photochemical proteolysis applied to ion channels in vivo.

Authors:  P M England; H A Lester; N Davidson; D A Dougherty
Journal:  Proc Natl Acad Sci U S A       Date:  1997-09-30       Impact factor: 11.205

Review 8.  An expanding genetic code.

Authors:  Jianming Xie; Peter G Schultz
Journal:  Methods       Date:  2005-07       Impact factor: 3.608

9.  Generation of a bacterium with a 21 amino acid genetic code.

Authors:  Ryan A Mehl; J Christopher Anderson; Stephen W Santoro; Lei Wang; Andrew B Martin; David S King; David M Horn; Peter G Schultz
Journal:  J Am Chem Soc       Date:  2003-01-29       Impact factor: 15.419

10.  Photoprocesses of molecules with 2-nitrobenzyl protecting groups and caged organic acids.

Authors:  Filiz Bley; Klaus Schaper; Helmut Görner
Journal:  Photochem Photobiol       Date:  2008 Jan-Feb       Impact factor: 3.421

View more
  20 in total

1.  Photochemical cleavage of leader peptides.

Authors:  Noah Bindman; Remco Merkx; Robert Koehler; Nicholas Herrman; Wilfred A van der Donk
Journal:  Chem Commun (Camb)       Date:  2010-11-02       Impact factor: 6.222

Review 2.  Beyond the canonical 20 amino acids: expanding the genetic lexicon.

Authors:  Travis S Young; Peter G Schultz
Journal:  J Biol Chem       Date:  2010-02-10       Impact factor: 5.157

3.  Hydrophobic Tags for Highly Efficient Light-Activated Protein Release.

Authors:  Karthik Nadendla; Bhagyesh R Sarode; Simon H Friedman
Journal:  Mol Pharm       Date:  2019-05-31       Impact factor: 4.939

Review 4.  At the Interface of Chemical and Biological Synthesis: An Expanded Genetic Code.

Authors:  Han Xiao; Peter G Schultz
Journal:  Cold Spring Harb Perspect Biol       Date:  2016-09-01       Impact factor: 10.005

5.  Synthesis and incorporation of a caged tyrosine amino acid possessing a bioorthogonal handle.

Authors:  Marshall S Padilla; Christopher A Farley; Lindsay E Chatkewitz; Douglas D Young
Journal:  Tetrahedron Lett       Date:  2016-09-10       Impact factor: 2.415

6.  Modular synthesis of biodegradable diblock copolymers for designing functional polymersomes.

Authors:  Joshua S Katz; Sheng Zhong; Brendon G Ricart; Darrin J Pochan; Daniel A Hammer; Jason A Burdick
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

Review 7.  Incorporation of Non-Canonical Amino Acids.

Authors:  Lilia Leisle; Francis Valiyaveetil; Ryan A Mehl; Christopher A Ahern
Journal:  Adv Exp Med Biol       Date:  2015       Impact factor: 2.622

8.  A selenide-based approach to photochemical cleavage of peptide and protein backbones at engineered backbone esters.

Authors:  Amy L Eastwood; Angela P Blum; Niki M Zacharias; Dennis A Dougherty
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

9.  Synthesis and evaluation of photoreactive tetrazole amino acids.

Authors:  Yizhong Wang; Qing Lin
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

10.  Evolution of amber suppressor tRNAs for efficient bacterial production of proteins containing nonnatural amino acids.

Authors:  Jiantao Guo; Charles E Melançon; Hyun Soo Lee; Dan Groff; Peter G Schultz
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.