For Publishers
DiscoveryMetadataPeer reviewHostingPublishing
For Researchers
JoinPublishReviewCollect
Register
Blog
About
Search
Advanced search
My ScienceOpen
Search
For Publishers
For Researchers
Blog
About
1
views
43
references
 Top references
cited by
0
    
0 reviews
 Review
0
comments
 Comment
0
recommends
+1 Recommend
0 collections
    0
    shares
      171
      similar
       All similar
      • Record: found
      • Abstract: found
      • Article: found
      Is Open Access

      Solid-Phase Synthesis of Head to Side-Chain Tyr-Cyclodepsipeptides Through a Cyclative Cleavage From Fmoc-MeDbz/MeNbz-resins

      research-article

      Read this article at

      ScienceOpenPublisherPMC
      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          Cyclic depsipeptides constitute a fascinating class of natural products. Most of them are characterized by an ester formed between the β-hydroxy function of Ser/Thr -and related amino acids- and the carboxylic group of the C-terminal amino acid. Less frequent are those where the thiol of Cys is involved rendering a thioester (cyclo thiodepsipeptides) and even less common are the cyclo depsipeptides with a phenyl ester coming from the side-chain of Tyr. Herein, the preparation of the later through a cyclative cleavage using the Fmoc-MeDbz/MeNbz-resin is described. This resin has previously reported for the synthesis of cyclo thiodepsipeptides and homodetic peptides. The use of that resin for the preparation of all these peptides is also summarized.

          Related collections

          Most cited references43

          • Record: found
          • Abstract: not found
          • Article: not found

          Peptide coupling reagents, more than a letter soup.

          Ayman El-Faham, Fernando Albericio (2011)
          Article 0 comments Cited 181 times – based on 0 reviews     Review now
            Bookmark
            • Record: found
            • Abstract: not found
            • Article: not found

            Amino acid-protecting groups.

            Albert Isidro-Llobet, Mercedes Álvarez, Fernando Albericio (2009)
            Article 0 comments Cited 126 times – based on 0 reviews     Review now
              Bookmark
              • Record: found
              • Abstract: found
              • Article: not found

              Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion.

              Rafel Prohens, Ramon Subirós-Funosas, Fernando Albericio … (2009)
              Oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate] has been tested as an additive for use in the carbodiimide approach for formation of peptide bonds. Its performance in relation to those of HOBt and HOAt, which have recently been reported to exhibit explosive properties, is reported. Oxyma displayed a remarkable capacity to inhibit racemization, together with impressive coupling efficiency in both automated and manual synthesis, superior to those of HOBt and at least comparable to those of HOAt, and surpassing the latter coupling agent in the more demanding peptide models. Stability assays showed that there was no risk of capping the resin under standard coupling conditions. Finally, calorimetry assays (DSC and ARC) showed decomposition profiles for benzotriazole-based additives that were consistent with their reported explosivities and suggested a lower risk of explosion in the case of Oxyma.
              Article 0 comments Cited 81 times – based on 0 reviews     Review now
                Bookmark
                All references

                Author and article information

                Contributors
                Journal
                Journal ID (nlm-ta): Front Chem
                Journal ID (iso-abbrev): Front Chem
                Journal ID (publisher-id): Front. Chem.
                Title: Frontiers in Chemistry
                Publisher: Frontiers Media S.A.
                ISSN (Electronic): 2296-2646
                Publication date (Electronic): 22 April 2020
                Publication date Collection: 2020
                Volume: 8
                Electronic Location Identifier: 298
                Affiliations
                [1] 1CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, University of Barcelona (UB) , Barcelona, Spain
                [2] 2Department of Organic Chemistry, University of Barcelona , Barcelona, Spain
                [3] 3Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), Spanish National Research Council (CSIC) , Barcelona, Spain
                [4] 4Associated Unit, Spanish National Research Council-University of Barcelona (CSIC-UB) , Barcelona, Spain
                [5] 5KwaZulu-Natal Research Innovation and Sequencing Platform (KRISP), School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal , Durban, South Africa
                [6] 6Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal , Durban, South Africa
                Author notes

                Edited by: Laszlo Otvos, Olpe LLC, United States

                Reviewed by: Mare Cudic, Florida Atlantic University, United States; Max Julian Cryle, Monash University, Australia

                *Correspondence: Fernando Albericio albericio@ 123456ukzn.ac.za

                This article was submitted to Chemical Biology, a section of the journal Frontiers in Chemistry

                Article
                DOI: 10.3389/fchem.2020.00298
                PMC ID: 7189019
                SO-VID: 32cf83bf-7aed-46a4-b154-f0b03baf8176
                Copyright © Copyright © 2020 Acosta, Murray, Royo, de la Torre and Albericio.
                License:

                This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

                History
                Date received : 11 February 2020
                Date accepted : 25 March 2020
                Page count
                Figures: 9, Tables: 1, Equations: 0, References: 50, Pages: 9, Words: 4834
                Funding
                Funded by: Ministerio de Economía, Industria y Competitividad, Gobierno de España 10.13039/501100010198
                Funded by: Departament d'Innovació, Universitats i Empresa, Generalitat de Catalunya 10.13039/501100002943
                Categories
                Subject: Chemistry
                Subject: Original Research

                Keywords: cyclothiodepsipeptides,heterodetic cyclic peptides,homodetic cyclic peptides,native chemical ligation,solid-phase peptide synthesis
                Data availability:
                Keywords: cyclothiodepsipeptides, heterodetic cyclic peptides, homodetic cyclic peptides, native chemical ligation, solid-phase peptide synthesis

                Comments

                Comment on this article