Literature DB >> 24392870

Efficient asymmetric synthesis of tryptophan analogues having useful photophysical properties.

Poulami Talukder1, Shengxi Chen, Pablo M Arce, Sidney M Hecht.   

Abstract

Two new fluorescent probes of protein structure and dynamics have been prepared by concise asymmetric syntheses using the Schöllkopf chiral auxiliary. The site-specific incorporation of one probe into dihydrofolate reductase is reported. The utility of these tryptophan derivatives lies in their absorption and emission maxima which differ from those of tryptophan, as well as in their large Stokes shifts and high molar absorptivities.

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Year:  2014        PMID： 24392870      PMCID： PMC3955165          DOI： 10.1021/ol403429e

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  A general method for site-specific incorporation of unnatural amino acids into proteins.

Authors:  C J Noren; S J Anthony-Cahill; M C Griffith; P G Schultz
Journal:  Science       Date:  1989-04-14       Impact factor: 47.728

2.  Detection of dihydrofolate reductase conformational change by FRET using two fluorescent amino acids.

Authors:  Shengxi Chen; Nour Eddine Fahmi; Lin Wang; Chandrabali Bhattacharya; Stephen J Benkovic; Sidney M Hecht
Journal:  J Am Chem Soc       Date:  2013-08-22       Impact factor: 15.419

3.  Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors.

Authors:  Chun-Hsu Yao; Jen-Shin Song; Chiung-Tong Chen; Teng-Kuang Yeh; Tsung-Chih Hsieh; Szu-Huei Wu; Chung-Yu Huang; Yu-Lin Huang; Min-Hsien Wang; Yu-Wei Liu; Chi-Hui Tsai; Chidambaram Ramesh Kumar; Jinq-Chyi Lee
Journal:  Eur J Med Chem       Date:  2012-07-04       Impact factor: 6.514

4.  Mischarging Escherichia coli tRNAPhe with L-4'-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenylalanine, a photoactivatable analogue of phenylalanine.

Authors:  G Baldini; B Martoglio; A Schachenmann; C Zugliani; J Brunner
Journal:  Biochemistry       Date:  1988-10-04       Impact factor: 3.162

5.  The use of 5'-phospho-2 deoxyribocytidylylriboadenosine as a facile route to chemical aminoacylation of tRNA.

Authors:  S A Robertson; C J Noren; S J Anthony-Cahill; M C Griffith; P G Schultz
Journal:  Nucleic Acids Res       Date:  1989-12-11       Impact factor: 16.971

6.  Azatryptophans endow proteins with intrinsic blue fluorescence.

Authors:  Sandra Lepthien; Michael G Hoesl; Lars Merkel; Nediljko Budisa
Journal:  Proc Natl Acad Sci U S A       Date:  2008-10-14       Impact factor: 11.205

7.  T4 RNA ligase mediated preparation of novel "chemically misacylated" tRNAPheS.

Authors:  T G Heckler; L H Chang; Y Zama; T Naka; M S Chorghade; S M Hecht
Journal:  Biochemistry       Date:  1984-03-27       Impact factor: 3.162

8.  Blue fluorescent amino acids as in vivo building blocks for proteins.

Authors:  Lars Merkel; Michael G Hoesl; Marcel Albrecht; Andreas Schmidt; Nediljko Budisa
Journal:  Chembiochem       Date:  2010-02-15       Impact factor: 3.164

9.  Dipeptide formation with misacylated tRNAPhes.

Authors:  T G Heckler; Y Zama; T Naka; S M Hecht
Journal:  J Biol Chem       Date:  1983-04-10       Impact factor: 5.157

10.  Conformational distribution of a 14-residue peptide in solution: a fluorescence resonance energy transfer study.

Authors:  Matthew J Tucker; Rolando Oyola; Feng Gai
Journal:  J Phys Chem B       Date:  2005-03-17       Impact factor: 2.991
  10 in total
  6 in total

1.  Enhanced Binding Affinity for an i-Motif DNA Substrate Exhibited by a Protein Containing Nucleobase Amino Acids.

Authors:  Xiaoguang Bai; Poulami Talukder; Sasha M Daskalova; Basab Roy; Shengxi Chen; Zhongxian Li; Larisa M Dedkova; Sidney M Hecht
Journal:  J Am Chem Soc       Date:  2017-03-17       Impact factor: 15.419

2.  Blue fluorescent amino acid for biological spectroscopy and microscopy.

Authors:  Mary Rose Hilaire; Ismail A Ahmed; Chun-Wei Lin; Hyunil Jo; William F DeGrado; Feng Gai
Journal:  Proc Natl Acad Sci U S A       Date:  2017-05-22       Impact factor: 11.205

3.  A Mild and General Larock Indolization Protocol for the Preparation of Unnatural Tryptophans.

Authors:  Kangway V Chuang; Madeleine E Kieffer; Sarah E Reisman
Journal:  Org Lett       Date:  2016-09-06       Impact factor: 6.005

4.  Tryptophan-based fluorophores for studying protein conformational changes.

Authors:  Poulami Talukder; Shengxi Chen; C Tony Liu; Edwin A Baldwin; Stephen J Benkovic; Sidney M Hecht
Journal:  Bioorg Med Chem       Date:  2014-09-16       Impact factor: 3.641

5.  Tuning the electronic transition energy of indole via substitution: application to identify tryptophan-based chromophores that absorb and emit visible light.

Authors:  Robert J Micikas; Ismail A Ahmed; Arusha Acharyya; Amos B Smith; Feng Gai
Journal:  Phys Chem Chem Phys       Date:  2021-03-12       Impact factor: 3.676

Review 6.  Miniaturized Chemical Tags for Optical Imaging.

Authors:  Sam Benson; Fabio de Moliner; William Tipping; Marc Vendrell
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-21       Impact factor: 16.823
  6 in total

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