Literature DB >> 23210918

New TFA-free cleavage and final deprotection in fmoc solid-phase peptide synthesis: dilute HCl in fluoro alcohol.

Pasquale Palladino1, Dmitry A Stetsenko.   

Abstract

A novel method for cleaving from resin and removing acid-labile protecting groups for the Fmoc solid-phase peptide synthesis is described. 0.1 N HCl in hexafluoroisopropanol or trifluoroethanol cleanly and rapidly removes the tert-butyl ester and ether, Boc, trityl, and Pbf groups and cleaves the common resin linkers: Wang, HMPA, Rink amide, and PAL. Addition of just 5-10% of a hydrogen-bonding solvent considerably retards or even fully inhibits the reaction. However, a non-hydrogen-bonding solvent is tolerated.

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Year:  2012        PMID： 23210918     DOI： 10.1021/ol303124r

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Chemical synthesis of proteins using peptide hydrazides as thioester surrogates.

Authors:  Ji-Shen Zheng; Shan Tang; Yun-Kun Qi; Zhi-Peng Wang; Lei Liu
Journal:  Nat Protoc       Date:  2013-11-14       Impact factor: 13.491

Review 2.  Greening the synthesis of peptide therapeutics: an industrial perspective.

Authors:  Vincent Martin; Peter H G Egelund; Henrik Johansson; Sebastian Thordal Le Quement; Felix Wojcik; Daniel Sejer Pedersen
Journal:  RSC Adv       Date:  2020-11-24       Impact factor: 4.036

Review 3.  Marine Cyclic Peptides: Antimicrobial Activity and Synthetic Strategies.

Authors:  Ricardo Ribeiro; Eugénia Pinto; Carla Fernandes; Emília Sousa
Journal:  Mar Drugs       Date:  2022-06-15       Impact factor: 6.085

4.  Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction.

Authors:  Hashim F Motiwala; Charlie Fehl; Sze-Wan Li; Erin Hirt; Patrick Porubsky; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2013-06-07       Impact factor: 15.419

5.  O-GlcNAcase Fragment Discovery with Fluorescence Polarimetry.

Authors:  Vladimir S Borodkin; Karim Rafie; Nithya Selvan; Tonia Aristotelous; Iva Navratilova; Andrew T Ferenbach; Daan M F van Aalten
Journal:  ACS Chem Biol       Date:  2018-05-02       Impact factor: 5.100

Review 6.  Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry.

Authors:  Anamika Sharma; Iván Ramos-Tomillero; Ayman El-Faham; Ernesto Nicolas; Hortensia Rodriguez; Beatriz G de la Torre; Fernando Albericio
Journal:  ChemistryOpen       Date:  2017-03-08       Impact factor: 2.911

7.  Rapid and Quantitative De-tert-butylation for Poly(acrylic acid) Block Copolymers and Influence on Relaxation of Thermoassociated Transient Networks.

Authors:  Alexei D Filippov; Ilse A van Hees; Remco Fokkink; Ilja K Voets; Marleen Kamperman
Journal:  Macromolecules       Date:  2018-10-12       Impact factor: 5.985

8.  1,4-Benzenedimethanethiol (1,4-BDMT) as a scavenger for greener peptide resin cleavages.

Authors:  Jan Pawlas; Thomas Svensson; Jon H Rasmussen
Journal:  RSC Adv       Date:  2019-11-28       Impact factor: 3.361

9.  Total Synthesis and Structure Correction of the Cyclic Lipodepsipeptide Orfamide A.

Authors:  Yuko Bando; Yu Hou; Lydia Seyfarth; Jannik Probst; Sebastian Götze; Marta Bogacz; Ute A Hellmich; Pierre Stallforth; Maria Mittag; Hans-Dieter Arndt
Journal:  Chemistry       Date:  2022-03-09       Impact factor: 5.020

10.  Sequence-defined positioning of amine and amide residues to control catechol driven wet adhesion.

Authors:  Lukas Fischer; Alexander K Strzelczyk; Nils Wedler; Christian Kropf; Stephan Schmidt; Laura Hartmann
Journal:  Chem Sci       Date:  2020-08-31       Impact factor: 9.825
  10 in total

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