Epimerization-Free C-Term Activation of Peptide Fragments by Ball Milling.

Peptides were produced in high yields and, if any, very low epimerization, by mechanochemical coupling of peptide fragments containing highly epimerization-prone and/or highly hindered amino acids at C-term. Ball milling was clearly identified as the key element enabling one to obtain such results.

[1]  Jean Martinez,et al.  From JMV-1843 to Macrilen , 2020 .

[2]  Zhènglì Shí,et al.  Inhibition of SARS-CoV-2 (previously 2019-nCoV) infection by a highly potent pan-coronavirus fusion inhibitor targeting its spike protein that harbors a high capacity to mediate membrane fusion , 2020, Cell Research.

[3]  C. Bolm,et al.  Direct Visualization of a Mechanochemically Induced Molecular Rearrangement. , 2020, Angewandte Chemie.

[4]  Cynthia Liu,et al.  Research and Development on Therapeutic Agents and Vaccines for COVID-19 and Related Human Coronavirus Diseases , 2020, ACS central science.

[5]  F. Albericio,et al.  2019 FDA TIDES (Peptides and Oligonucleotides) Harvest , 2020, Pharmaceuticals.

[6]  L. Gentilucci,et al.  Green synthesis of bioactive oligopeptides promoted by recyclable nanocrystalline hydroxyapatite. , 2020, Future medicinal chemistry.

[7]  H. Titi,et al.  Mechanochemistry for Synthesis. , 2019, Angewandte Chemie.

[8]  J. Pawlas,et al.  ReGreen SPPS: enabling circular chemistry in environmentally sensible solid-phase peptide synthesis , 2019, Green Chemistry.

[9]  O. Melnyk,et al.  Native Chemical Ligation and Extended Methods: Mechanisms, Catalysis, Scope, and Limitations. , 2019, Chemical reviews.

[10]  R. Payne,et al.  Native chemical ligation in protein synthesis and semi-synthesis. , 2018, Chemical Society reviews.

[11]  Jean Martínez,et al.  Peptide Couplings by Reactive Extrusion: Solid-Tolerant and Free from Carcinogenic, Mutagenic and Reprotoxic Chemicals , 2018, ACS Sustainable Chemistry and Engineering.

[12]  C. Bolm,et al.  From Synthesis of Amino Acids and Peptides to Enzymatic Catalysis: A Bottom-Up Approach in Mechanochemistry. , 2018, ChemSusChem.

[13]  James Mack,et al.  Mechanochemistry and organic synthesis: from mystical to practical , 2018 .

[14]  T. Friščić,et al.  Enthalpy vs. friction: heat flow modelling of unexpected temperature profiles in mechanochemistry of metal–organic frameworks† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc05312f , 2018, Chemical science.

[15]  James C. Collins,et al.  The Current State of Peptide Drug Discovery: Back to the Future? , 2017, Journal of medicinal chemistry.

[16]  Jolene L. Lau,et al.  Therapeutic peptides: Historical perspectives, current development trends, and future directions. , 2017, Bioorganic & medicinal chemistry.

[17]  Jean Martínez,et al.  A mechanochemical approach to access the proline–proline diketopiperazine framework , 2017, Beilstein journal of organic chemistry.

[18]  R. Raines,et al.  Peptides on the Rise. , 2017, Accounts of chemical research.

[19]  Teng Zhang,et al.  Full solution-phase synthesis of acetyl hexapeptide-3 by fragments coupling strategy , 2017 .

[20]  Jean Martínez,et al.  Peptide synthesis: ball-milling, in solution, or on solid support, what is the best strategy? , 2017, Beilstein journal of organic chemistry.

[21]  C. Klein,et al.  Phenylglycine racemization in Fmoc-based solid-phase peptide synthesis: Stereochemical stability is achieved by choice of reaction conditions , 2017 .

[22]  Christiane Maierhofer,et al.  Warming up for mechanosynthesis - temperature development in ball mills during synthesis. , 2017, Chemical communications.

[23]  Shinichiro Fuse,et al.  Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation , 2016, Nature Communications.

[24]  Jean Martínez,et al.  Peptide Mechanosynthesis by Direct Coupling of N‐Protected α‐Amino Acids with Amino Esters , 2016 .

[25]  Jean Martínez,et al.  Amino Acids and Peptides in Ball Milling , 2015 .

[26]  Teng Zhang,et al.  Kilogram-Scale Synthesis of Osteogenic Growth Peptide (10–14) Using a Fragment Coupling Approach , 2015 .

[27]  Fernando Albericio,et al.  Peptide synthesis beyond DMF: THF and ACN as excellent and friendlier alternatives. , 2015, Organic & biomolecular chemistry.

[28]  B. Ranu,et al.  Ball Milling Towards Green Synthesis: Applications, Projects, Challenges , 2014 .

[29]  J. V. van Maarseveen,et al.  Epimerization-free C-terminal peptide activation. , 2013, Chemistry.

[30]  Jean Martínez,et al.  Environmentally benign peptide synthesis using liquid-assisted ball-milling: application to the synthesis of Leu-enkephalin , 2013 .

[31]  Helen F. Sneddon,et al.  Evaluation of alternative solvents in common amide coupling reactions: replacement of dichloromethane and N,N-dimethylformamide , 2013 .

[32]  O. Melnyk,et al.  Sequential native peptide ligation strategies for total chemical protein synthesis. , 2012, Chemical Society reviews.

[33]  M. Elsawy,et al.  Racemisation of N‐Fmoc phenylglycine under mild microwave‐SPPS and conventional stepwise SPPS conditions: attempts to develop strategies for overcoming this , 2012, Journal of peptide science : an official publication of the European Peptide Society.

[34]  Fernando Albericio,et al.  Peptide coupling reagents, more than a letter soup. , 2011, Chemical reviews.

[35]  E. Juaristi,et al.  Green synthesis of α,β- and β,β-dipeptides under solvent-free conditions. , 2010, The Journal of organic chemistry.

[36]  M. Khrestchatisky,et al.  Synthetic therapeutic peptides: science and market. , 2010, Drug discovery today.

[37]  Jean Martínez,et al.  Solvent-free synthesis of peptides. , 2009, Angewandte Chemie.

[38]  Fernando Albericio,et al.  Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion. , 2009, Chemistry.

[39]  S. Childs,et al.  The role of solvent in mechanochemical and sonochemical cocrystal formation: a solubility-based approach for predicting cocrystallisation outcome , 2009 .

[40]  F. Albericio,et al.  A novel protecting/activating strategy for beta-hydroxy acids and its use in convergent peptide synthesis. , 2008, The Journal of organic chemistry.

[41]  R. Patel,et al.  Large-scale synthesis of hematoregulatory nonapeptide SK&F 107647 by fragment coupling. , 1999, The journal of peptide research : official journal of the American Peptide Society.

[42]  Yongxin Han,et al.  Occurrence and Minimization of Cysteine Racemization during Stepwise Solid-Phase Peptide Synthesis(1)(,)(2). , 1997, The Journal of organic chemistry.

[43]  R A Houghten,et al.  Peptide libraries: Determination of relative reaction rates of protected amino acids in competitive couplings , 1994, Biopolymers.

[44]  G. Smith,et al.  Mechanism of the racemization of amino acids. Kinetics of racemization of arylglycines , 1983 .

[45]  Jean Martinez,et al.  Side Reactions in Peptide Synthesis , 1978 .