Serine-Selective Bioconjugation.

The first general method for the rapid, chemoselective, and modular functionalization of serine residues in native polypeptides is reported using a reagent platform based on P(V) oxidation state. This redox-economic approach can be used to append nearly any kind of cargo onto serine, generating a stable, benign, and hydrophilic phosphorothioate linkage. The method tolerates all other known nucleophilic functional groups of naturally occurring proteinogenic amino acids. A variety of applications can be envisaged by this expansion of the toolbox of site-selective bioconjugation methods.

[1]  Julien C. Vantourout,et al.  Synthetic Elaboration of Native DNA by RASS (SENDR) , 2020, ACS central science.

[2]  Xiaoshu Jing,et al.  A gold mine for drug discovery: Strategies to develop cyclic peptides into therapies , 2020, Medicinal research reviews.

[3]  Martin D. Eastgate,et al.  Enantiodivergent Formation of C-P Bonds: Synthesis of P-Chiral Phosphines and Methyl-phosphonate Oligonucleotides. , 2020, Journal of the American Chemical Society.

[4]  Vishal Rai,et al.  Chemical Methods for Selective Labeling of Proteins , 2019, European Journal of Organic Chemistry.

[5]  Andy Chi-Lung Lee,et al.  A Comprehensive Review on Current Advances in Peptide Drug Development and Design , 2019, International journal of molecular sciences.

[6]  S. Shuto,et al.  Development of a Highly Potent Analogue and a Long-Acting Analogue of Oxytocin for the Treatment of Social Impairment-Like Behaviors. , 2019, Journal of medicinal chemistry.

[7]  Emily A. Hoyt,et al.  Contemporary approaches to site-selective protein modification , 2019, Nature Reviews Chemistry.

[8]  Christopher J. Chang,et al.  Bioinspired Thiophosphorodichloridate Reagents for Chemoselective Histidine Bioconjugation. , 2018, Journal of the American Chemical Society.

[9]  Martin D. Eastgate,et al.  Unlocking P(V): Reagents for chiral phosphorothioate synthesis , 2018, Science.

[10]  Han Liu,et al.  Serine/Threonine Ligation: Origin, Mechanistic Aspects, and Applications. , 2018, Accounts of chemical research.

[11]  J. Gonçalves,et al.  Vancomycin therapeutic drug monitoring and population pharmacokinetic models in special patient subpopulations , 2018, Pharmacology research & perspectives.

[12]  Chad J. Miller,et al.  Homing in: Mechanisms of Substrate Targeting by Protein Kinases. , 2018, Trends in biochemical sciences.

[13]  Phil S Baran,et al.  Residue-Specific Peptide Modification: A Chemist's Guide. , 2017, Biochemistry.

[14]  C. Heinis,et al.  Cyclic peptide therapeutics: past, present and future. , 2017, Current opinion in chemical biology.

[15]  D. Boger,et al.  Peripheral modifications of [Ψ[CH2NH]Tpg4]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics , 2017, Proceedings of the National Academy of Sciences.

[16]  Igor L. Medintz,et al.  Chemoselective and Bioorthogonal Ligation Reactions: Concepts and Applications , 2017 .

[17]  David Komander,et al.  Ubiquitin modifications , 2016, Cell Research.

[18]  N. Grishin,et al.  A Single Kinase Generates the Majority of the Secreted Phosphoproteome , 2015, Cell.

[19]  Gonçalo J L Bernardes,et al.  Advances in chemical protein modification. , 2015, Chemical reviews.

[20]  Kevin Y. Yip,et al.  Identification of a Major Determinant for Serine-Threonine Kinase Phosphoacceptor Specificity , 2014, Molecular cell.

[21]  M. Bakermans-Kranenburg,et al.  Sniffing around oxytocin: review and meta-analyses of trials in healthy and clinical groups with implications for pharmacotherapy , 2013, Translational Psychiatry.

[22]  Jui-Yoa Chang,et al.  Rapid and irreversible reduction of protein disulfide bonds. , 2010, Analytical biochemistry.

[23]  H. Chaimovich,et al.  Thiolysis and alcoholysis of phosphate tri- and monoesters with alkyl and aryl leaving groups. An ab initio study in the gas phase. , 2005, The journal of physical chemistry. A.

[24]  T. Hunter,et al.  The Protein Kinase Complement of the Human Genome , 2002, Science.

[25]  A. Ciechanover,et al.  The ubiquitin-proteasome proteolytic pathway: destruction for the sake of construction. , 2002, Physiological reviews.

[26]  J. Denu,et al.  Molecular reactions of protein phosphatases--insights from structure and chemistry. , 2001, Chemical reviews.

[27]  D. Boger.  Vancomycin, teicoplanin, and ramoplanin: Synthetic and mechanistic studies † , 2001, Medicinal research reviews.

[28]  J. Denu,et al.  Molecular Reactions of Protein PhosphatasesInsights from Structure and Chemistry , 2001 .

[29]  P. Kennelly,et al.  Protein phosphatases--a phylogenetic perspective. , 2001, Chemical reviews.

[30]  G. Gimpl,et al.  The oxytocin receptor system: structure, function, and regulation. , 2001, Physiological reviews.

[31]  P. Cohen,et al.  The regulation of protein function by multisite phosphorylation--a 25 year update. , 2000, Trends in biochemical sciences.

[32]  C. Pickart,et al.  Ubiquitin in chains. , 2000, Trends in biochemical sciences.

[33]  D. Boger,et al.  Total Synthesis of the Vancomycin Aglycon , 1999 .

[34]  R. Hughes,et al.  Total Synthesis of Vancomycin , 1999 .

[35]  L. Johnson,et al.  Structural basis for control by phosphorylation. , 1997, Chemical reviews.

[36]  W. Stec,et al.  Mechanism of the Chemoselective and Stereoselective Ring Opening of Oxathiaphospholanes: An Ab Initio Study , 1997 .

[37]  W. Stec,et al.  Ab initio investigation on nucleophilic ring opening of 1,3,2-oxathiaphospholane: nucleophilic substitution at phosphorus coupled with pseudorotation , 1996 .

[38]  G. Whitesides,et al.  Reagents for Rapid Reduction of Native Disulfide Bonds in Proteins , 1994 .

[39]  S. Harrison,et al.  The complex between phage 434 repressor DNA-binding domain and operator site OR3: structural differences between consensus and non-consensus half-sites. , 1993, Structure.

[40]  David A. Dixon,et al.  Ab initio conformational analysis of cyclohexane , 1990 .

[41]  F. Westheimer.  Why nature chose phosphates. , 1987, Science.

[42]  F. Bushman,et al.  Activation of transcription by the bacteriophage 434 repressor. , 1986, Proceedings of the National Academy of Sciences of the United States of America.

[43]  J. Petersen,et al.  Steric and electronic effects on the stereochemistry of the alkaline hydrolysis of acyclic dialkoxyphosphonium salts. Pseudorotation of intermediates in phosphorus ester reactions , 1972 .

[44]  D. B. Boyd.  Mechanism of hydrolysis of cyclic phosphate esters , 1969 .

[45]  F. Westheimer.  Pseudo-rotation in the hydrolysis of phosphate esters , 1968 .

[46]  D. Koshland,et al.  The conversion of serine at the active site of subtilisin to cysteine: a "chemical mutation". , 1966, Proceedings of the National Academy of Sciences of the United States of America.

[47]  L. Polgár,et al.  A New Enzyme Containing a Synthetically Formed Active Site. Thiol-Subtilisin1 , 1966 .

[48]  I. Um,et al.  Kinetic Study on Nucleophilic Displacement Reactions of Phenyl Y‐Substituted Phenyl Carbonates with 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene: Effects of Amine Nature on Reaction Mechanism , 2016 .

[49]  G. Koudelka.  Recognition of DNA structure by 434 repressor. , 1998, Nucleic acids research.

[50]  N. E. Brandon,et al.  Hydroxyl group catalysis. II. The reactivity of the hydroxyl group of serine. The nucleophilicity of alcohols and the ease of hydrolysis of their acetyl esters as related to their pKa. , 1962, Biochemistry.