Site-specific chemical modification of peptide and protein by thiazolidinediones.

A direct aldol reaction employing 2,4-thiazolidinediones as nucleophilic donors was performed to modify peptides and protein under mild conditions. Various functional groups could be readily introduced into protein without conformation change.

[1]  M. Francis,et al.  Dual-surface modification of the tobacco mosaic virus. , 2005, Journal of the American Chemical Society.

[2]  Adam Heller,et al.  Electrochemical glucose sensors and their applications in diabetes management. , 2008, Chemical reviews.

[3]  H. Vogel,et al.  Labeling of fusion proteins with synthetic fluorophores in live cells. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[4]  De‐Cai Xiong,et al.  Enabling Wittig reaction on site-specific protein modification. , 2012, Chemical communications.

[5]  Carolyn R Bertozzi,et al.  Introducing genetically encoded aldehydes into proteins. , 2007, Nature chemical biology.

[6]  Harm-Anton Klok,et al.  Peptide/protein-polymer conjugates: synthetic strategies and design concepts. , 2008, Chemical communications.

[7]  T. Keller,et al.  Functionalization of peptides and proteins by Mukaiyama aldol reaction. , 2010, Journal of the American Chemical Society.

[8]  J. Errey,et al.  Facile conversion of cysteine and alkyl cysteines to dehydroalanine on protein surfaces: versatile and switchable access to functionalized proteins. , 2008, Journal of the American Chemical Society.

[9]  K. Rose,et al.  Construction of protein analogues by site-specific condensation of unprotected fragments. , 1992, Bioconjugate chemistry.

[10]  Yiming Li,et al.  Engineered fluorescence tags for in vivo protein labelling , 2014 .

[11]  Do ligand binding and solvent exclusion alter the electrostatic character within the oxyanion hole of an enzymatic active site? , 2007, Journal of the American Chemical Society.

[12]  Ronald T Raines,et al.  Hydrolytic stability of hydrazones and oximes. , 2008, Angewandte Chemie.

[13]  Yiran Wang,et al.  C‐Terminal Incorporation of Bio‐Orthogonal Azide Groups into a Protein and Preparation of Protein–Oligodeoxynucleotide Conjugates by CuI‐Catalyzed Cycloaddition , 2007, Chembiochem : a European journal of chemical biology.

[14]  P. Dawson,et al.  Nucleophilic catalysis of oxime ligation. , 2006, Angewandte Chemie.

[15]  Jennifer A. Prescher,et al.  Finding the right (bioorthogonal) chemistry. , 2014, ACS chemical biology.

[16]  A. Tiwari,et al.  An uncatalyzed aldol reaction of thiazolidinediones , 2012 .

[17]  A. Dondoni.  Die Entwicklung der Thiol‐En‐Kupplung als Klick‐Prozess für die Materialwissenschaften und die bioorganische Chemie , 2008 .

[18]  C. Bertozzi,et al.  Site-specific chemical modification of recombinant proteins produced in mammalian cells by using the genetically encoded aldehyde tag , 2009, Proceedings of the National Academy of Sciences.

[19]  Pete Crisalli,et al.  Water-soluble organocatalysts for hydrazone and oxime formation. , 2013, The Journal of organic chemistry.

[20]  D. Burton,et al.  A Glycoconjugate Antigen Based on the Recognition Motif of a Broadly Neutralizing Human Immunodeficiency Virus Antibody, 2G12, Is Immunogenic but Elicits Antibodies Unable To Bind to the Self Glycans of gp120 , 2008, Journal of Virology.

[21]  M. Francis,et al.  Protein-cross-linked polymeric materials through site-selective bioconjugation. , 2008, Angewandte Chemie.

[22]  M. Francis,et al.  Tyrosine-selective protein alkylation using pi-allylpalladium complexes. , 2006, Journal of the American Chemical Society.

[23]  C. Rizzo,et al.  CHAOTROPIC SALT EFFECTS IN A HYDROPHOBICALLY ACCELERATED DIELS-ALDER REACTION , 1991 .

[24]  Jennifer A. Prescher,et al.  Functionalized cyclopropenes as bioorthogonal chemical reporters. , 2012, Journal of the American Chemical Society.

[25]  Neel S. Joshi,et al.  N-terminal protein modification through a biomimetic transamination reaction. , 2006, Angewandte Chemie.

[26]  Tsubasa Okano,et al.  Dry and wet prolines for asymmetric organic solvent-free aldehyde-aldehyde and aldehyde-ketone aldol reactions. , 2007, Chemical communications.

[27]  D. Parker.  Tumour targeting with radiolabelled macrocycle–antibody conjugates , 1990 .

[28]  Peng R. Chen,et al.  Genetically encoded alkenyl–pyrrolysine analogues for thiol–ene reaction mediated site-specific protein labeling , 2012 .

[29]  Tsubasa Sasaki,et al.  N-terminal labeling of proteins by the Pictet-Spengler reaction. , 2008, Bioorganic & medicinal chemistry letters.

[30]  Fei Liu,et al.  Labeling proteins with small molecules by site-specific posttranslational modification. , 2004, Journal of the American Chemical Society.

[31]  M. Francis,et al.  Optimization of a biomimetic transamination reaction. , 2008, Journal of the American Chemical Society.

[32]  T. Kodadek,et al.  Techniques: Oxidative cross-linking as an emergent tool for the analysis of receptor-mediated signalling events. , 2005, Trends in pharmacological sciences.

[33]  W. Humphreys,et al.  Strategy and its implications of protein bioanalysis utilizing high-resolution mass spectrometric detection of intact protein. , 2011, Analytical chemistry.

[34]  M. Francis,et al.  Reductive alkylation of proteins using iridium catalyzed transfer hydrogenation. , 2005, Journal of the American Chemical Society.

[35]  J. V. Hest,et al.  Bioorthogonal chemistry in living organisms , 2014 .

[36]  K. Rose,et al.  High yield, site-specific coupling of N-terminally modified beta-lactamase to a proteolytically derived single-sulfhydryl murine Fab'. , 1994, Bioconjugate chemistry.

[37]  M. Distefano,et al.  A highly efficient catalyst for oxime ligation and hydrazone-oxime exchange suitable for bioconjugation. , 2013, Bioconjugate chemistry.

[38]  S. W. Kim,et al.  Effects of PEG conjugation on insulin properties. , 2002, Advanced drug delivery reviews.

[39]  J. Reek,et al.  Transition-metal catalysis as a tool for the covalent labeling of proteins. , 2006, Angewandte Chemie.

[40]  S. Weiss,et al.  Efficient site-specific labeling of proteins via cysteines. , 2008, Bioconjugate chemistry.

[41]  Joseph M. Fox,et al.  Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity. , 2008, Journal of the American Chemical Society.