Judit Tulla-Puche

Summary

Publications

  1. doi request reprint Enzyme-labile protecting groups for the synthesis of natural products: solid-phase synthesis of thiocoraline
    Judit Tulla-Puche
    Institute for Research in Biomedicine Barcelona, CIBER BBN, Baldiri Reixac 10, 08028 Barcelona Spain
    Angew Chem Int Ed Engl 52:5726-30. 2013
  2. doi request reprint NMe amide as a synthetic surrogate for the thioester moiety in thiocoraline
    Judit Tulla-Puche
    Institute for Research in Biomedicine, Barcelona Science Park, 08028 Barcelona, Spain
    J Med Chem 52:834-9. 2009
  3. doi request reprint Protection by conformationally restricted mobility: first solid-phase synthesis of triostin A
    Judit Tulla-Puche
    Institute for Research in Biomedicine, Barcelona Science Park, Barcelona, Spain
    Chemistry 14:4475-8. 2008
  4. ncbi request reprint Solid-phase synthesis of oxathiocoraline by a key intermolecular disulfide dimer
    Judit Tulla-Puche
    Institute for Research in Biomedicine, Barcelona Science Park, 08028 Barcelona, Spain, PharmaMar, S A U, 28770 Colmenar Viejo, Madrid, Spain
    J Am Chem Soc 129:5322-3. 2007
  5. doi request reprint Optimized Fmoc solid-phase synthesis of the cysteine-rich peptide linaclotide
    Miriam Góngora-Benítez
    Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain
    Biopolymers 96:69-80. 2011
  6. ncbi request reprint Total solid-phase synthesis of the azathiocoraline class of symmetric bicyclic peptides
    Núria Bayó-Puxan
    Barcelona Biomedical Research Institute, University of Barcelona, Barcelona Science Park PCB, 08028 Barcelona, Spain
    Chemistry 12:9001-9. 2006
  7. doi request reprint Acid-labile Cys-protecting groups for the Fmoc/tBu strategy: filling the gap
    Miriam Góngora-Benítez
    Institute for Research in Biomedicine, 08028 Barcelona, Spain
    Org Lett 14:5472-5. 2012
  8. doi request reprint ChemMatrix(®) for complex peptides and combinatorial chemistry
    Yésica García-Ramos
    Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, Barcelona, Spain
    J Pept Sci 16:675-8. 2010
  9. ncbi request reprint From the one-bead-one-compound concept to one-bead-one-reactor
    Mariela M Marani
    Institute for Research in Biomedicine, Barcelona Science Park, Josep Samitier 1 5, 08028 Barcelona, Spain
    J Comb Chem 9:395-8. 2007
  10. doi request reprint Understanding acid lability of cysteine protecting groups
    Iván Ramos-Tomillero
    Institute for Research in Biomedicine IRB Barcelona, Baldiri Reixac 10, 08028 Barcelona, Spain
    Molecules 18:5155-62. 2013

Collaborators

  • Fernando Albericio
  • Jan Spengler
  • Marta Pelay-Gimeno
  • Peter White
  • Pablo Cironi
  • George Barany
  • Luis J Cruz
  • Miriam Góngora-Benítez
  • Yésica García-Ramos
  • Eleonora Marcucci
  • Iván Ramos-Tomillero
  • Fayna Garcia-Martin
  • Matthieu Giraud
  • Marta Paradís-Bas
  • Núria Bayó-Puxan
  • Simon Côté
  • Lorena Mendive-Tapia
  • Gemma Vilar
  • Irina V Getun
  • Mariela M Marani
  • Tommaso Cupido
  • Ernesto Nicolas
  • Miriam Royo
  • Arjen C Breman
  • Michèle Cristau
  • Alessandra Basso
  • Thomas Bruckdorfer
  • Oleg Werbitzky
  • Clare Woodward
  • C Kent Brown
  • Douglas Ohlendorf
  • Silvia A Camperi
  • Osvaldo Cascone
  • Mercedes Alvarez
  • Carmen Cuevas
  • Catherine Gravel
  • Estela Riego
  • Martina Quintanar-Audelo
  • Robert Furic
  • Ariadna Fernandez
  • René Steinauer

Detail Information

Publications29

  1. doi request reprint Enzyme-labile protecting groups for the synthesis of natural products: solid-phase synthesis of thiocoraline
    Judit Tulla-Puche
    Institute for Research in Biomedicine Barcelona, CIBER BBN, Baldiri Reixac 10, 08028 Barcelona Spain
    Angew Chem Int Ed Engl 52:5726-30. 2013
    ..One-pot cleavage of the phenylacetamidomethyl protecting group using immobilized penicillin G acylase enzyme and disulfide formation are the key steps of the synthetic strategy...
  2. doi request reprint NMe amide as a synthetic surrogate for the thioester moiety in thiocoraline
    Judit Tulla-Puche
    Institute for Research in Biomedicine, Barcelona Science Park, 08028 Barcelona, Spain
    J Med Chem 52:834-9. 2009
    ..Moreover, NMe-azathiocoraline displayed an increased stability in human serum as compared to the parent natural product. This approach could be used in other depsipeptides and side chain to side chain cyclic peptides...
  3. doi request reprint Protection by conformationally restricted mobility: first solid-phase synthesis of triostin A
    Judit Tulla-Puche
    Institute for Research in Biomedicine, Barcelona Science Park, Barcelona, Spain
    Chemistry 14:4475-8. 2008
  4. ncbi request reprint Solid-phase synthesis of oxathiocoraline by a key intermolecular disulfide dimer
    Judit Tulla-Puche
    Institute for Research in Biomedicine, Barcelona Science Park, 08028 Barcelona, Spain, PharmaMar, S A U, 28770 Colmenar Viejo, Madrid, Spain
    J Am Chem Soc 129:5322-3. 2007
  5. doi request reprint Optimized Fmoc solid-phase synthesis of the cysteine-rich peptide linaclotide
    Miriam Góngora-Benítez
    Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain
    Biopolymers 96:69-80. 2011
    ..Here we describe an optimized solid-phase synthesis of linaclotide that should allow the production of this peptide in multigram amounts...
  6. ncbi request reprint Total solid-phase synthesis of the azathiocoraline class of symmetric bicyclic peptides
    Núria Bayó-Puxan
    Barcelona Biomedical Research Institute, University of Barcelona, Barcelona Science Park PCB, 08028 Barcelona, Spain
    Chemistry 12:9001-9. 2006
    ..The heterocyclic moiety was added in the last step of the synthesis to assist the preparation of libraries of new compounds with potential therapeutic applications...
  7. doi request reprint Acid-labile Cys-protecting groups for the Fmoc/tBu strategy: filling the gap
    Miriam Góngora-Benítez
    Institute for Research in Biomedicine, 08028 Barcelona, Spain
    Org Lett 14:5472-5. 2012
    ..S-Dpm proved to be compatible with the commonly used S-Trt group and was applied for the regioselecive construction of disulfide bonds...
  8. doi request reprint ChemMatrix(®) for complex peptides and combinatorial chemistry
    Yésica García-Ramos
    Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, Barcelona, Spain
    J Pept Sci 16:675-8. 2010
    ..Furthermore, the high loading of this resin permits the use of a tiny quarter of a bead as a microreactor for HPLC and MALDI-TOF analysis, thus further extending its applications in the field of combinatorial chemistry...
  9. ncbi request reprint From the one-bead-one-compound concept to one-bead-one-reactor
    Mariela M Marani
    Institute for Research in Biomedicine, Barcelona Science Park, Josep Samitier 1 5, 08028 Barcelona, Spain
    J Comb Chem 9:395-8. 2007
    ..The four bead parts show high homogeneity and can thus be considered to be replicas...
  10. doi request reprint Understanding acid lability of cysteine protecting groups
    Iván Ramos-Tomillero
    Institute for Research in Biomedicine IRB Barcelona, Baldiri Reixac 10, 08028 Barcelona, Spain
    Molecules 18:5155-62. 2013
    ..All the optimized geometries and energies presented in this study were determined using a B3LYP/6-31G(d,p) calculation. The results discussed herein may be of broader applicability for the development of new protecting groups...
  11. ncbi request reprint Cysteine-S-trityl a key derivative to prepare N-methyl cysteines
    Eleonora Marcucci
    Institute for Research in Biomedicine, Barcelona Science Park, 08028 Barcelona, Spain
    J Comb Chem 10:69-78. 2008
    ..Thus, this convenient route allows us to obtain many different protected NMe-Cys, which were of limited accessibility until now...
  12. doi request reprint The first total synthesis of the cyclodepsipeptide pipecolidepsin A
    Marta Pelay-Gimeno
    1 Institute for Research in Biomedicine, Baldiri Reixac 10, 08028 Barcelona, Spain 2 CIBER BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, 08028 Barcelona, Spain
    Nat Commun 4:2352. 2013
    ....
  13. doi request reprint Eco-friendly combination of the immobilized PGA enzyme and the S-Phacm protecting group for the synthesis of Cys-containing peptides
    Miriam Góngora-Benítez
    Institute for Research in Biomedicine, 08028 Barcelona, Spain
    Chemistry 18:16166-76. 2012
    ..Herein, the versatility and reliability of an eco-friendly combination of the immobilized PGA enzyme and the S-Phacm protecting group has been evaluated for the synthesis of diverse Cys-containing peptides...
  14. doi request reprint Solid-phase synthesis of NMe-IB-01212, a highly N-methylated cyclic peptide
    Eleonora Marcucci
    Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain
    Org Lett 14:612-5. 2012
    ..The resulting NMe-IB-01212 exhibits micromolar activity and considerable stability...
  15. doi request reprint Synthesis of orthogonally protected L-threo-beta-ethoxyasparagine
    Jan Spengler
    Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028, Barcelona, Spain
    Amino Acids 39:161-5. 2010
    ..Thus, a significant amount of 1 (1.8 g) was obtained in 21% overall yield. The synthesis reported is also expected to be useful for the preparation of other O-substituted L-threo-beta-hydroxyasparagine derivatives...
  16. doi request reprint Constella™(EU)-Linzess™(USA): the last milestone in the long journey of the peptide linaclotide and its implications for the future of peptide drugs
    Miriam Góngora-Benítez
    Institute for Research in Biomedicine, Barcelona Science Park, 08028 Barcelona, Spain
    Future Med Chem 5:291-300. 2013
    ..Particularly, the pharmacodynamic and pharmacokinetic properties of linaclotide, a small, disulfide-rich peptide, and its implications in the future of peptide drug discovery and development are discussed...
  17. doi request reprint A universal strategy for preparing protected C-terminal peptides on the solid phase through an intramolecular click chemistry-based handle
    Miriam Góngora-Benítez
    Institute for Research in Biomedicine, Barcelona Science Park PCB, Baldiri Reixac 10, 08028 Barcelona, Spain
    Chem Commun (Camb) 48:2313-5. 2012
    ....
  18. ncbi request reprint The synthesis of naturally occurring peptides and their analogs
    Tommaso Cupido
    Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1 5, Barcelona, Spain
    Curr Opin Drug Discov Devel 10:768-83. 2007
    ..This review provides an overview of the current state of peptide synthesis methodology, focusing mainly on the synthesis of natural peptides and their analogs...
  19. doi request reprint N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate (TCFH), a powerful coupling reagent for bioconjugation
    Judit Tulla-Puche
    Institute for Research in Biomedicine, Combinatorial Chemistry Unit, CIBER BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, 08028 Barcelona, Spain
    Bioconjug Chem 19:1968-71. 2008
    ..In contrast, the use of N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate (TCFH) resulted in good yields of ester prodrugs of thiocoraline and could be applicable to other drugs with similar limitations...
  20. ncbi request reprint ChemMatrix, a poly(ethylene glycol)-based support for the solid-phase synthesis of complex peptides
    Fayna Garcia-Martin
    Barcelona Biomedical Research Institute, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028 Barcelona, Spain
    J Comb Chem 8:213-20. 2006
    ..In addition to the difficulties of its synthesis, characterization of the beta-amyloid (1-42) peptide as a monomer is also a challenge, and methods for characterization by HPLC and MALDI-TOF have also been developed...
  21. ncbi request reprint The synergy of ChemMatrix resin and pseudoproline building blocks renders RANTES, a complex aggregated chemokine
    Fayna Garcia-Martin
    Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028 Barcelona, Spain
    Biopolymers 84:566-75. 2006
    ..Here we report on an efficient stepwise solid-phase synthesis of RANTES (1-68) by combining the advantages of the totally PEG-based ChemMatrix resin and pseudoproline dipeptides...
  22. doi request reprint Optimized Fmoc solid-phase synthesis of Thymosin alpha1 by side-chain anchoring onto a PEG resin
    Yésica García-Ramos
    Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain
    Biopolymers 92:565-72. 2009
    ..Here we report a straightforward stepwise solid-phase synthesis on a polyethylene glycol solid-support that enables the scaling-up of this key therapeutic peptide...
  23. pmc "Head-to-side-chain" cyclodepsipeptides of marine origin
    Marta Pelay-Gimeno
    Institute for Research in Biomedicine, Baldiri Reixac 10, Barcelona 08028, Spain
    Mar Drugs 11:1693-717. 2013
    ..This structural pattern, the presence of unique and complex residues, and relevant bioactivity are the main features shared by all the members of this new class of depsipeptides, which are reviewed herein...
  24. doi request reprint Handles for fmoc solid-phase synthesis of protected peptides
    Miriam Góngora-Benítez
    Institute for Research in Biomedicine IRB Barcelona, 08028 Barcelona, Spain
    ACS Comb Sci 15:217-28. 2013
    ....
  25. doi request reprint Rescuing biological activity from synthetic phakellistatin 19
    Marta Pelay-Gimeno
    Institute for Research in Biomedicine Barcelona, Baldiri Reixac 10, 08028 Barcelona, Spain
    J Med Chem 56:9780-8. 2013
    ....
  26. doi request reprint Orthogonal Chemistry for the Synthesis of Thiocoraline-Triostin Hybrids. Exploring their Structure-Activity Relationship
    Judit Tulla-Puche
    Institute for Research in Biomedicine Barcelona, Baldiri Reixac 10, 08028 Barcelona, Spain
    J Med Chem 56:5587-600. 2013
    ..In vitro studies and structure-activity relationships have been shown trends in the structure-activity relationship that will facilitate the design of new bisintercalators. ..
  27. ncbi request reprint Polymers and drug delivery systems
    Gemma Vilar
    Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain
    Curr Drug Deliv 9:367-94. 2012
    ..These polymeric systems have been used for a range of treatments for antineoplastic activity, bacterial infections and inflammatory processes, in addition to vaccines...
  28. ncbi request reprint Solid-phase syntheses of furopyridine and furoquinoline systems
    Pablo Cironi
    Biomedical Research Institute, Barcelona Scientific Park, Laboratory of Organic Chemistry, Faculty of Pharmacy, and Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain
    Org Lett 6:1405-8. 2004
    ..Reactions were monitored "in situ" in real time by a variety of spectroscopic techniques, which allowed full and accurate control of progress in these syntheses...
  29. ncbi request reprint Partially folded bovine pancreatic trypsin inhibitor analogues attain fully native structures when co-crystallized with S195A rat trypsin
    Irina V Getun
    Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA
    J Mol Biol 375:812-23. 2008
    ....